Do you like this cute little babydoll nightie? i just love it.
Bedtime can be so much fun for a sissy like me!
Good night everyone.
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Bedtime can be so much fun for a sissy like me!
Good night everyone.
6/29/12
Being Jake's Sissy
It was a wonderful Friday morning. i was up early to see Diane off to work and couldn't wait to see Jake. He was supposed to be coming over around 8 to pick me up for a golf game, at least that was what he told his wife Nancy. Instead, we stayed here and played "other games." Diane was gone by 7:30 and told me to have fun and "be a good girl for your man." i love how She teases me.
i wore a read bra and panty set with a white polo shirt, some very short and tight ladies's short shorts and some pink sandals. i was hoping i wasn't overdoing it and that Jake would like what he saw. i didn't want to dress to the nine's with a dress, heels, makeup, etc. You could see the red bra through the polo shirt and i liked that. i hoped he would to. Slowly, i want him to see me as a feminine man, playing the role of his woman.
When the doorbell rang i minced over to open the door and greet him. i could tell he liked what he saw but seemed a little nervous. i told him not to worry, that Diane wouldn't be home until the middle of the afternoon at the earliest. It would be the start of a long weekend for Her, since She's taking Monday and Tuesday off next week.
Jake told me how nice i looked and when i closed the door, i stood in front of him and told him he looked pretty hot too. i had brewed a fresh pot of coffee and offered him some. He accepted and we made our way to the kitchen. i felt so submissive as i poured him a cup and served it to him at the counter we have. As i put the cup down in front of him, he ran his hand over my ass and it felt so nice. Instinctively, i kissed him. He responded passionately. i was on his lap and we were embracing. It got hot pretty quick, while the coffee got cold.
"Would you like to go to the bedroom?" I asked him, "we can bring our coffees." He thought that was a good idea and he followed me to the guest bedroom I had decided we would use.
"I have to admit that I've been thinking of you sucking my cock all week" he said. "So have i" i told him. If i had told him the truth, he would have known that i'd actually dreamed about it also.
"Why don't you get naked for me? I love to watch a woman get undressed." He said. i'll remember those words forever - he used the word "woman".....the fact that he referred to me that way made me feel as special as i ever had with a man.
i slipped the sandals off and then slid the tight short shorts off. After taking off my shirt, i stood in front of him in my red bra and panties. He held me close again and kissed me, running his hands on my ass and his fingers along the outline of the bra cups. i felt so much like a woman. i turned around and unhooked the bra and let it slide to the floor. "You do that so elegantly" he said, "you must be used to it." That made me giggle. If he only knew the whole story about how Diane had me practice putting on and taking off bras!
Soon, i was naked and on my knees before him at the foot of the bed. He had me undo his pants and told me to start sucking him before his pants were even lowered. He got hard and fully erect very quickly. i took my time. i wanted to treat his cock gently and lovingly. From the sounds he was making, he appreciated my efforts.
The best part was how he talked to me. The words "good girl" made me swoon. He was more verbal than our first two meetings. i loved that. Finally, i figured it was time for me to say something to him. "i love being your girl. i want to be your sissy."
i could tell from his reaction that he loved that. His moans were followed by an aggressive thrusting of his cock into my mouth. "Then be a good sissy girl and please me" he said.
Yes, i pleased him this morning. More than once. i wonder if he knows just how much i'm pleasing myself when doing so.
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i wore a read bra and panty set with a white polo shirt, some very short and tight ladies's short shorts and some pink sandals. i was hoping i wasn't overdoing it and that Jake would like what he saw. i didn't want to dress to the nine's with a dress, heels, makeup, etc. You could see the red bra through the polo shirt and i liked that. i hoped he would to. Slowly, i want him to see me as a feminine man, playing the role of his woman.
When the doorbell rang i minced over to open the door and greet him. i could tell he liked what he saw but seemed a little nervous. i told him not to worry, that Diane wouldn't be home until the middle of the afternoon at the earliest. It would be the start of a long weekend for Her, since She's taking Monday and Tuesday off next week.
Jake told me how nice i looked and when i closed the door, i stood in front of him and told him he looked pretty hot too. i had brewed a fresh pot of coffee and offered him some. He accepted and we made our way to the kitchen. i felt so submissive as i poured him a cup and served it to him at the counter we have. As i put the cup down in front of him, he ran his hand over my ass and it felt so nice. Instinctively, i kissed him. He responded passionately. i was on his lap and we were embracing. It got hot pretty quick, while the coffee got cold.
"Would you like to go to the bedroom?" I asked him, "we can bring our coffees." He thought that was a good idea and he followed me to the guest bedroom I had decided we would use.
"I have to admit that I've been thinking of you sucking my cock all week" he said. "So have i" i told him. If i had told him the truth, he would have known that i'd actually dreamed about it also.
"Why don't you get naked for me? I love to watch a woman get undressed." He said. i'll remember those words forever - he used the word "woman".....the fact that he referred to me that way made me feel as special as i ever had with a man.i slipped the sandals off and then slid the tight short shorts off. After taking off my shirt, i stood in front of him in my red bra and panties. He held me close again and kissed me, running his hands on my ass and his fingers along the outline of the bra cups. i felt so much like a woman. i turned around and unhooked the bra and let it slide to the floor. "You do that so elegantly" he said, "you must be used to it." That made me giggle. If he only knew the whole story about how Diane had me practice putting on and taking off bras!
The best part was how he talked to me. The words "good girl" made me swoon. He was more verbal than our first two meetings. i loved that. Finally, i figured it was time for me to say something to him. "i love being your girl. i want to be your sissy."
i could tell from his reaction that he loved that. His moans were followed by an aggressive thrusting of his cock into my mouth. "Then be a good sissy girl and please me" he said.
Yes, i pleased him this morning. More than once. i wonder if he knows just how much i'm pleasing myself when doing so.
6/27/12
Sissy Sex with Diane
Yesterday afternoon Diane called me from Her office around 4:30. She was using Her speakerphone, which always makes me feel uncomfortable, even though She's assured me that our conversation is private. There have been a few times where She's told me to hold on and put me on hold while someone comes into Her office. i still get nervous.
"Would you like some sissy sex tonight when I get home" she asked me and, with just a slight pause added "I would" before i could even answer. i told Her i would enjoy that. "Good, get yourself looking pretty for me and have the strap-on and stuff ready and I'll be home by 6 o'clock" She said and hung up.
i was ready well before 6, a pink flowered babyoll top with matching bikini panties and some pink ballet type slippers were all i wore. i debated whether or not i should put a touch of makeup on or some jewelry but decided against it. The bed was taken down and Diane's strap-on, lubricant and a couple of small towels also lay on the bed, ready for Her use.
She hadn't arrived by 6:30 so i called Her cell phone and when it rang, i could tell from the beep at the end of the ring that She was on a call, so i hung up without leaving a message. A few minutes later She called back and said She was just a few minutes away. "You're just a horny little sissy and can't wait" She laughed.
Indeed a few minutes later She was walking through the door and it didn't take Her long to slip out of Her clothes and into the strap-on. As She did, i admired Her body and how beautiful She looked to me. When She was done, i approached Her and started to kiss Her softly on the lips and and touch Her arms softly.
"Don't be wasting time. Get your girly bottom on the bed and show me how much you want it" she barked, somewhat out of character. Our lovemaking is usually soft and sensual, but last night it had a much different feel to it. When i lay on my back and spread my legs, Diane immediately told me to turn over because She wanted to take me doggie style.
The softness in style that i usually enjoy was replaced by a firmness that i wasn't familiar with. She was far more verbal with me. i can't remember how many times She used the term "sissy". She made me beg for Her "cock", making me tell Her how much i loved Her "cock." There were plenty of slaps on my bottom also between the Hard strokes of the strap-on.
The difference was noticeable, even though i couldn't describe it exactly, then just before i climaxed as She seemed to be deeper inside of me then She'd ever been, i realized what it was. There was more of a "manliness" to Her lovemaking. i came like a woman, letting out some deep moans and cries as my juices dampened the towel Diane had placed under me. It was an awesome orgasm.
Later, i couldn't help but wonder if Diane's approach to our lovemaking was a reflection of some of the things She had done with Brian. Was She treating me like Brian treated Her? Rougher? More manly? More verbal? She called me Her sissy very often while She made love to me. Did Brian have a special name for Her?
my sissy cuckold mind was working overtime last night.
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"Would you like some sissy sex tonight when I get home" she asked me and, with just a slight pause added "I would" before i could even answer. i told Her i would enjoy that. "Good, get yourself looking pretty for me and have the strap-on and stuff ready and I'll be home by 6 o'clock" She said and hung up.
i was ready well before 6, a pink flowered babyoll top with matching bikini panties and some pink ballet type slippers were all i wore. i debated whether or not i should put a touch of makeup on or some jewelry but decided against it. The bed was taken down and Diane's strap-on, lubricant and a couple of small towels also lay on the bed, ready for Her use.
She hadn't arrived by 6:30 so i called Her cell phone and when it rang, i could tell from the beep at the end of the ring that She was on a call, so i hung up without leaving a message. A few minutes later She called back and said She was just a few minutes away. "You're just a horny little sissy and can't wait" She laughed.
Indeed a few minutes later She was walking through the door and it didn't take Her long to slip out of Her clothes and into the strap-on. As She did, i admired Her body and how beautiful She looked to me. When She was done, i approached Her and started to kiss Her softly on the lips and and touch Her arms softly.
"Don't be wasting time. Get your girly bottom on the bed and show me how much you want it" she barked, somewhat out of character. Our lovemaking is usually soft and sensual, but last night it had a much different feel to it. When i lay on my back and spread my legs, Diane immediately told me to turn over because She wanted to take me doggie style.
The difference was noticeable, even though i couldn't describe it exactly, then just before i climaxed as She seemed to be deeper inside of me then She'd ever been, i realized what it was. There was more of a "manliness" to Her lovemaking. i came like a woman, letting out some deep moans and cries as my juices dampened the towel Diane had placed under me. It was an awesome orgasm.
Later, i couldn't help but wonder if Diane's approach to our lovemaking was a reflection of some of the things She had done with Brian. Was She treating me like Brian treated Her? Rougher? More manly? More verbal? She called me Her sissy very often while She made love to me. Did Brian have a special name for Her?
my sissy cuckold mind was working overtime last night.
6/25/12
My Tennis Panties
i felt so feminine this morning, almost devilishly so. Maybe because i'm all excited about my upcoming dates with Jake and how well things are going. i keep thinking about how hot it was to go down on him before our golf date the other day, right in his dining room!
i couldn't help myself today. i slipped some ruffled tennis panties on along with a pleated tennis skirt and matching top (i put some taupe colored pantyhose on also to make my legs look a little more tan) and just twirled around over and over so that my panties were exposed when the skirt lifted. It felt so good. i even went outside for a bit and did the same. i was in a very secluded area of our property, so there was almost no chance of my being seen. i felt so naughty!
i got so excited that when i came in, i laid on the bed and stroked myself softly until i came in the panties.
i know it's silly, but sometimes sissies just have to get certain things out of their systems.
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i got so excited that when i came in, i laid on the bed and stroked myself softly until i came in the panties.
i know it's silly, but sometimes sissies just have to get certain things out of their systems.
6/24/12
Sissy Dates
My golf date with Jake went real well on Friday. i picked him up at his house in the afternoon and even though there was no one around, we didn't want to take the chance to fool around just in case his wife came home early. Well, we fooled around just a little bit! He wanted to see the panties i was wearing and when i lowered my shorts to show him, he didn't hesitate to have me turn around and model them for him. He also caressed my butt which immediately sent me swooning and got me aroused.
i wasn't the only one aroused! Jake took my hand and put it over his crotch. i loved the feeling and couldn't help myself. Instinctively, i was on my knees in his kitchen and feeling for his cock. He stopped me, but only briefly, so we could move over to the dining room where he could stand and see if anyone was coming up the driveway! His home is set about 40 or 50 yards from the road and the dining room window allowed him to see anyone driving up to the house.
i felt so submissive and feminine on my knees taking care of Jake's masculine needs. At the same time, i was fulfilling needs of my own. The need to serve. The need to feel like a man's "wife", "girlfriend" or "sissy." The need to please. And the need to feel a man in my mouth. i was totally aroused but didn't touch myself. i hoped Jake wouldn't make me play with myself like the last time and he didn't. Sometimes, the Dominant's pleasure is more than satisfying for a submissive.
The golf was fun. Of course, we shared the same cart and Jay would often sneak a nice feel on my smooth legs. i really loved that. We also got a chance to talk. At one point, he told me that he'd like to have me wear a bra, maybe just a sports bra, when we played golf. i was surprised at that comment but so happy. It made me feel like he was enjoying my femininity and would be willing to exploit it even more.
We also talked about future dates. We're going to meet some day this week, possibly at my place and i want to wear something special for him. We also talked about the possibility of going on a golfing weekend together! i'm not sure how much golf we would play but the thought of spending a weekend with him would be so awesome!
When we got back to his place his wife was there and Jake introduced me to her. Nancy seemed very nice and was both welcoming and hospitable. She asked if we wanted something to drink and some snacks so i stayed a little while and chatted. She asked if my wife played golf and i jokingly answered that the fact that she didn't was probably the secret to our successful marriage. She laughed about that and said that she also didn't play. The meeting went well and Jake seemed like he was relaxed about it. i thought he looked a little tense at first but by the time i left, he was fine.
In closing today's post, i do have to say that meeting Jake has been really great for me. However, it does bring up a small dilemma that i've been struggling with internally for several weeks. Ken, the man i had an affair with until he moved away, will be visiting in a couple of weeks. i told Jake about Ken, but not that i was planning to see him while he was here. i've thought it over and gone back and forth. As much as i wanted to see Ken and play with him, things have changed and i wouldn't feel right being intimate with him while doing the same with Jake.
i know it sounds silly, but when i met Jake, we were both looking for a regular friendship that wouldn't involve running around with others. i know i would be disappointed if Jake saw an old friend of his and had sex with him. i've decided that i'm probably going to have lunch with Ken or something like that but no sex. i hope he understands.
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i wasn't the only one aroused! Jake took my hand and put it over his crotch. i loved the feeling and couldn't help myself. Instinctively, i was on my knees in his kitchen and feeling for his cock. He stopped me, but only briefly, so we could move over to the dining room where he could stand and see if anyone was coming up the driveway! His home is set about 40 or 50 yards from the road and the dining room window allowed him to see anyone driving up to the house.
i felt so submissive and feminine on my knees taking care of Jake's masculine needs. At the same time, i was fulfilling needs of my own. The need to serve. The need to feel like a man's "wife", "girlfriend" or "sissy." The need to please. And the need to feel a man in my mouth. i was totally aroused but didn't touch myself. i hoped Jake wouldn't make me play with myself like the last time and he didn't. Sometimes, the Dominant's pleasure is more than satisfying for a submissive.
The golf was fun. Of course, we shared the same cart and Jay would often sneak a nice feel on my smooth legs. i really loved that. We also got a chance to talk. At one point, he told me that he'd like to have me wear a bra, maybe just a sports bra, when we played golf. i was surprised at that comment but so happy. It made me feel like he was enjoying my femininity and would be willing to exploit it even more.
We also talked about future dates. We're going to meet some day this week, possibly at my place and i want to wear something special for him. We also talked about the possibility of going on a golfing weekend together! i'm not sure how much golf we would play but the thought of spending a weekend with him would be so awesome!
When we got back to his place his wife was there and Jake introduced me to her. Nancy seemed very nice and was both welcoming and hospitable. She asked if we wanted something to drink and some snacks so i stayed a little while and chatted. She asked if my wife played golf and i jokingly answered that the fact that she didn't was probably the secret to our successful marriage. She laughed about that and said that she also didn't play. The meeting went well and Jake seemed like he was relaxed about it. i thought he looked a little tense at first but by the time i left, he was fine.
In closing today's post, i do have to say that meeting Jake has been really great for me. However, it does bring up a small dilemma that i've been struggling with internally for several weeks. Ken, the man i had an affair with until he moved away, will be visiting in a couple of weeks. i told Jake about Ken, but not that i was planning to see him while he was here. i've thought it over and gone back and forth. As much as i wanted to see Ken and play with him, things have changed and i wouldn't feel right being intimate with him while doing the same with Jake.
i know it sounds silly, but when i met Jake, we were both looking for a regular friendship that wouldn't involve running around with others. i know i would be disappointed if Jake saw an old friend of his and had sex with him. i've decided that i'm probably going to have lunch with Ken or something like that but no sex. i hope he understands.
6/23/12
A Day for Sissies?
Earlier today i read All Mine, a blog written by Ms. Suzanne which is one of my favorites, and discovered that yesterday was "No Panty Day." i don't think i would have risked upsetting Jake by not wearing panties for our golf date, and i doubt this special day was created with sissies like me in mind. Who would want to go a full day without panties anyway?
After reading Ms. Suzanne's post, i did some research of my own and found out that today is actually "National Pink Day." Were it not for reading All Mine today, this quasi-sissy holiday would have totally passed me by.
Diane is gone to a baby shower this afternoon and now that i've finished all my housework i'm going to take a bubble bath and get dressed into something very, very pink before She gets home!
Don't you think there should be a National Sissy Day?
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Diane is gone to a baby shower this afternoon and now that i've finished all my housework i'm going to take a bubble bath and get dressed into something very, very pink before She gets home!
Don't you think there should be a National Sissy Day?
6/22/12
Cuckolding Keepsakes
My business trip lasted a day longer than planned this week, so i didn't get home until pretty late last night. Diane knew what time i'd be home, which flight i was on, its status, etc., so She was able to plan Her time with Brian right down to the minute if She wanted to. Brian was in town this week and they got to hook up twice; Wednesday and Thursday nights.
i suspected they would get together this week, but didn't know for sure until after i got home. As is typical of Diane, She withheld the information from me, instead mentally teasing me by making me wonder if She was in our bed with Brian while i was away. As it turns out, Brian was in our bed making love to Diane right around the time my flight landed.
Diane was waiting for me when i got home. Waiting to be serviced orally after what She called "two awesome fucks" with Brian. It was just another way for Her to taunt me. She was in her black satin robe and looked like a woman who had just been completely satisfied by a "real man." Only she still wasn't totally satisfied. In Her opinion, "cuckolding isn't complete until the sissy cleans the wife."
Even though Brian used a condom (i know because the used ones were still laying on some tissues on the nightstand), Diane insists there's still cleaning up to do. "The tenderness of your soft tongue is so soothing after deep fucking with Brian" she tells me.
As i lay between Her legs, licking Her well used pussy, She tells me how She and Brian may soon eliminate the condoms. "You'd like that wouldn't you?" She asks, not expecting an answer since my lips are busy. i get harder and She knows the thought excites me. "I'd enjoy it too" She says, "knowing that you'll be able to taste my lover so intimately. I've tasted him too you know. Directly from the source."
Like any good submissive, i can tell when She's ready to cum. She's stopped talking to me and soon She's in the throes of another orgasm, holding my head in place and telling me to "Suck and lick." When it subsided, She even thanked me and told me to lie on my back. i rolled over and felt a wet spot on the bed that I hadn't noticed before. A wet spot from Diane's lovemaking with Brian.
i can feel the dampness of their juices on the middle of my back as Diane spreads Her gorgeous ass cheeks over my face. i lick Her ass without being told. She is facing my feet and can see how hard my little cock is as it juts out of the panties. As i lick, she begins to toy with it softly, "sissy masturbation" or "milking" style.
"You know, Brian's mentioned several times how he'd like to fuck my ass" She tells me. "I bet you'd like to clean that mess up wouldn't you?"
With those words, i couldn't help myself and made a mess, cumming on Diane's hand and in my panties. She slid the panties off of me and cleaned up the mess with them. She told me to keep licking Her. "You just started for God's sake" She said.
When She had had enough, She got off of me and walked into the bathroom. i couldn't help but notice that She left my cum filled panties on the nightstand, right next to the condoms filled with Brian's cum. It's a cuckolding moment i'll ever forget. i gazed at it in somewhat of a trance until Diane said "You don't have to change the bed tonight. It's late. Do it in the morning." i slept on the damp spot. It was on my side of the bed.
i did my housework this morning and changed the bed. i'm now getting ready to have lunch then drive over to pick up Jake for our golf game this afternoon. i'll be wearing pink panties just like he told me. i guess i was born to take orders.
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i suspected they would get together this week, but didn't know for sure until after i got home. As is typical of Diane, She withheld the information from me, instead mentally teasing me by making me wonder if She was in our bed with Brian while i was away. As it turns out, Brian was in our bed making love to Diane right around the time my flight landed.
Diane was waiting for me when i got home. Waiting to be serviced orally after what She called "two awesome fucks" with Brian. It was just another way for Her to taunt me. She was in her black satin robe and looked like a woman who had just been completely satisfied by a "real man." Only she still wasn't totally satisfied. In Her opinion, "cuckolding isn't complete until the sissy cleans the wife."
Even though Brian used a condom (i know because the used ones were still laying on some tissues on the nightstand), Diane insists there's still cleaning up to do. "The tenderness of your soft tongue is so soothing after deep fucking with Brian" she tells me.
As i lay between Her legs, licking Her well used pussy, She tells me how She and Brian may soon eliminate the condoms. "You'd like that wouldn't you?" She asks, not expecting an answer since my lips are busy. i get harder and She knows the thought excites me. "I'd enjoy it too" She says, "knowing that you'll be able to taste my lover so intimately. I've tasted him too you know. Directly from the source."
Like any good submissive, i can tell when She's ready to cum. She's stopped talking to me and soon She's in the throes of another orgasm, holding my head in place and telling me to "Suck and lick." When it subsided, She even thanked me and told me to lie on my back. i rolled over and felt a wet spot on the bed that I hadn't noticed before. A wet spot from Diane's lovemaking with Brian.
i can feel the dampness of their juices on the middle of my back as Diane spreads Her gorgeous ass cheeks over my face. i lick Her ass without being told. She is facing my feet and can see how hard my little cock is as it juts out of the panties. As i lick, she begins to toy with it softly, "sissy masturbation" or "milking" style.
"You know, Brian's mentioned several times how he'd like to fuck my ass" She tells me. "I bet you'd like to clean that mess up wouldn't you?"
With those words, i couldn't help myself and made a mess, cumming on Diane's hand and in my panties. She slid the panties off of me and cleaned up the mess with them. She told me to keep licking Her. "You just started for God's sake" She said.
When She had had enough, She got off of me and walked into the bathroom. i couldn't help but notice that She left my cum filled panties on the nightstand, right next to the condoms filled with Brian's cum. It's a cuckolding moment i'll ever forget. i gazed at it in somewhat of a trance until Diane said "You don't have to change the bed tonight. It's late. Do it in the morning." i slept on the damp spot. It was on my side of the bed.
i did my housework this morning and changed the bed. i'm now getting ready to have lunch then drive over to pick up Jake for our golf game this afternoon. i'll be wearing pink panties just like he told me. i guess i was born to take orders.
6/19/12
Sissy Notes
It's been a few days since i've posted. A busy weekend filled with housework and some travel early this week because of my part-time consulting job has kept me very busy. When all the traditional "women's" work in a household falls on your shoulders, there's usually not much free time.
i'm not sure what Diane's plans are to meet with Brian this week while i'm away or, perhaps She doesn't even have any. She's continuing to keep me in the dark about when they meet until the very last moment possible if that's necessary or, after the fact whenever She can.
Diane is also a little bit upset because i haven't updated the blog format like She insisted a few weeks ago. i wrote about it in this post, but haven't gotten it done yet. My delay has led Her to tell me that if She "...was into corporal punishment, you'd be in for quite the beating. Instead, I'll have to think of some other punishment. Keep in mind that the longer you delay, the more severe it will be."
i started to update the blog's format twice, but made a few mistakes and didn't have the time to start over. i promised Her to get it done as soon as possible, especially with some unknown punishment hovering over my head. Diane is not into the physical aspects of Dominance very much, but certainly has the potential to be very creative when dealing out Her own form of discipline.
i'm tentatively supposed to play golf with Jake on Friday. He was so pleased with the way things went the last time we played and he got to meet Diane, he now thinks it might be a good idea for me to meet his wife Nancy! He might think it's a good idea but i'm a little nervous. i'm sure it will be fine being introduced as a golfing friend and it will help make getting together for future dates easier.
Finally, i thought my readers might enjoy this little article and video clip since you all know how important i think it is for sissies to learn how to put on a bra properly:
How to Put on a Bra: A Video Tutorial
Also, the star of the video is my kind of woman!
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i'm not sure what Diane's plans are to meet with Brian this week while i'm away or, perhaps She doesn't even have any. She's continuing to keep me in the dark about when they meet until the very last moment possible if that's necessary or, after the fact whenever She can.
Diane is also a little bit upset because i haven't updated the blog format like She insisted a few weeks ago. i wrote about it in this post, but haven't gotten it done yet. My delay has led Her to tell me that if She "...was into corporal punishment, you'd be in for quite the beating. Instead, I'll have to think of some other punishment. Keep in mind that the longer you delay, the more severe it will be."
i started to update the blog's format twice, but made a few mistakes and didn't have the time to start over. i promised Her to get it done as soon as possible, especially with some unknown punishment hovering over my head. Diane is not into the physical aspects of Dominance very much, but certainly has the potential to be very creative when dealing out Her own form of discipline.
i'm tentatively supposed to play golf with Jake on Friday. He was so pleased with the way things went the last time we played and he got to meet Diane, he now thinks it might be a good idea for me to meet his wife Nancy! He might think it's a good idea but i'm a little nervous. i'm sure it will be fine being introduced as a golfing friend and it will help make getting together for future dates easier.
Finally, i thought my readers might enjoy this little article and video clip since you all know how important i think it is for sissies to learn how to put on a bra properly:
How to Put on a Bra: A Video Tutorial
Also, the star of the video is my kind of woman!
6/16/12
A Sissy Cuckold and Her Boyfriend
This is a real difficult blog post for me. i'm struggling with what to say and how to say it for a couple of different reasons.
i had my first real "date" with Jake yesterday. By real, i mean that finally we had the opportunity to be intimate with each other. Both of us were very nervous, even though there was no chance that Diane would come home. In fact, She told me early Friday morning that She would be out of town for most of the day at a meeting. This seemed to make Jake a little more comfortable but it was still our first time together so there was a natural nervousness.
He got over it pretty quickly though, and that made me feel real, real good. He knew i was wearing panties and asked if i was wearing anything else. i told him i wasn't so he asked me if i'd like to put something pretty on for him. Of course i agreed but in my mind i was hoping he would be a little more forceful and demanding, TELLING me to put something on instead of just asking. Maybe in time.
i came back in a short yellow nightie, kind of like a babydoll but not quite. i also wore white high heels and even had a faux pearl necklace on. Jake just loved it. He had me model it for him. i stood in front of him and in my most feminine and coquettish manner, twirled around, curtsied and bent over so he could look me over. Things just got better from there and i pulled me close to him and put me on my knees while he sat on the loveseat in our living room.
Soon after i started this blog, i decided that i wouldn't get into overly graphic sex scenes. i wanted to keep it more R-rated than anything else. That's one of the things i'm struggling with. How do i keep it R-rated and still be able to convey the intimacy that took place between Jay and i? Or, do i abandon that philosophy and tell everyone everything that happened, in explicit detail? For now, i hope you can read between the lines. i will tell you that i serviced Jake three times with my mouth, and he promised to come back for more.
i was also happy that my submissive side was more than satisfied, particularly since there was no reciprocation on his part. It's just me, but i don't look at a Dominant Man and expect him to go down on me. i'd enjoy it with another sissy, but not a Real Man. Instead, Jake wanted me to masturbate in front of him. i did, and did it in my usual sissy way. He just loved that....thought it was so "F*&%(^ hot" - his exact words.
When he left, he told me to "be a good girl" and he kissed me. That was totally awesome.
Diane got home a little later than usual last night due to her out of town meeting. She called and told me to make sure i was dressed pretty for Her, something casual but feminine so we could enjoy a glass of wine together. After pouring the wine and setting out some cheese and crackers, She asked me how my "date" with Jake went. She wanted to know absolutely everything, down to the smallest detail. Diane took it all in and really made me feel comfortable. Her encouragement and support was really uplifting.
When I asked Her how Her day went and Her out of town meeting, the answer I got shocked the heck out of me. Her out of town meeting was actually a hook up with Brian. "I didn't want to tell you about it this morning because I figured you were nervous enough about your first time with Jake" She said.
"It's my turn to tell you about my date" She said with a big smile on Her face, "you can also ask me anything you want." She went on to tell me all that happened that afternoon with Brian. i didn't ask any questions. i didn't have to. She was very explicit.
When She was done telling me about Her date, She told me to follow Her to the bedroom. "I could use a nice licking" She told me.
As i began to worship Her, She asked me "Do I taste different?"
She did and i told her so.
"Do you like it?" She asked.
"Yes Diane. i do." i told Her. To be totally honest, i loved it.
"It was nice that we were both with our boyfriends today" She said, not expecting an answer.
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i had my first real "date" with Jake yesterday. By real, i mean that finally we had the opportunity to be intimate with each other. Both of us were very nervous, even though there was no chance that Diane would come home. In fact, She told me early Friday morning that She would be out of town for most of the day at a meeting. This seemed to make Jake a little more comfortable but it was still our first time together so there was a natural nervousness.
He got over it pretty quickly though, and that made me feel real, real good. He knew i was wearing panties and asked if i was wearing anything else. i told him i wasn't so he asked me if i'd like to put something pretty on for him. Of course i agreed but in my mind i was hoping he would be a little more forceful and demanding, TELLING me to put something on instead of just asking. Maybe in time.
i came back in a short yellow nightie, kind of like a babydoll but not quite. i also wore white high heels and even had a faux pearl necklace on. Jake just loved it. He had me model it for him. i stood in front of him and in my most feminine and coquettish manner, twirled around, curtsied and bent over so he could look me over. Things just got better from there and i pulled me close to him and put me on my knees while he sat on the loveseat in our living room.
Soon after i started this blog, i decided that i wouldn't get into overly graphic sex scenes. i wanted to keep it more R-rated than anything else. That's one of the things i'm struggling with. How do i keep it R-rated and still be able to convey the intimacy that took place between Jay and i? Or, do i abandon that philosophy and tell everyone everything that happened, in explicit detail? For now, i hope you can read between the lines. i will tell you that i serviced Jake three times with my mouth, and he promised to come back for more.
i was also happy that my submissive side was more than satisfied, particularly since there was no reciprocation on his part. It's just me, but i don't look at a Dominant Man and expect him to go down on me. i'd enjoy it with another sissy, but not a Real Man. Instead, Jake wanted me to masturbate in front of him. i did, and did it in my usual sissy way. He just loved that....thought it was so "F*&%(^ hot" - his exact words.
When he left, he told me to "be a good girl" and he kissed me. That was totally awesome.
Diane got home a little later than usual last night due to her out of town meeting. She called and told me to make sure i was dressed pretty for Her, something casual but feminine so we could enjoy a glass of wine together. After pouring the wine and setting out some cheese and crackers, She asked me how my "date" with Jake went. She wanted to know absolutely everything, down to the smallest detail. Diane took it all in and really made me feel comfortable. Her encouragement and support was really uplifting.
When I asked Her how Her day went and Her out of town meeting, the answer I got shocked the heck out of me. Her out of town meeting was actually a hook up with Brian. "I didn't want to tell you about it this morning because I figured you were nervous enough about your first time with Jake" She said.
"It's my turn to tell you about my date" She said with a big smile on Her face, "you can also ask me anything you want." She went on to tell me all that happened that afternoon with Brian. i didn't ask any questions. i didn't have to. She was very explicit.
When She was done telling me about Her date, She told me to follow Her to the bedroom. "I could use a nice licking" She told me.
As i began to worship Her, She asked me "Do I taste different?"
She did and i told her so.
"Do you like it?" She asked.
"Yes Diane. i do." i told Her. To be totally honest, i loved it.
"It was nice that we were both with our boyfriends today" She said, not expecting an answer.
6/13/12
"What Color Panties....
...are you wearing today?" Jake asked me as soon as i answered his call yesterday afternoon. It was the very first thing he said and i felt excited and relieved at the same time. Excited just by the way he said it; dominant, firm and demanding of an answer. Within the question lied the insinuation that i had better be wearing panties. Relieved that the question was proof that he was more interested in my feminine side that i thought. The fears i relayed in one of my earlier posts were more imagined than real.
"i'm wearing pink ones" i told him.
"Describe them to me" he said.
i went on to describe the pair of pink, size 6, cotton candy colored Jockey bikini panties i was wearing. They were sort of "striped", with two different shades of pink stripes running horizontally on the panties, one stripe a deeper shade of pink than the other to provide contrast. i own several similar pairs, mostly pink but one in white and another in blue.
"I bet you look very sexy in them" he said. i blushed, not knowing what to say. "i try to" i said.
"Good girl" he answered.
Wow. What a feeling to hear that from him. It made me feel so feminine and in need of his attention.
We talked for about 20 minutes. Jake admitted that it was a good idea to meet Diane and even suggested that at some point I meet his wife so that she could also view me as a new friend or golfing buddy. We're going to try to meet this Friday at the gym and i will have him over "for coffee" after our workout! Diane will be at work and it will be just the two of us. i'm a little nervous, hoping that everything goes just right!
read more
"i'm wearing pink ones" i told him.
"Describe them to me" he said.
i went on to describe the pair of pink, size 6, cotton candy colored Jockey bikini panties i was wearing. They were sort of "striped", with two different shades of pink stripes running horizontally on the panties, one stripe a deeper shade of pink than the other to provide contrast. i own several similar pairs, mostly pink but one in white and another in blue.
"I bet you look very sexy in them" he said. i blushed, not knowing what to say. "i try to" i said.
"Good girl" he answered.
Wow. What a feeling to hear that from him. It made me feel so feminine and in need of his attention.
We talked for about 20 minutes. Jake admitted that it was a good idea to meet Diane and even suggested that at some point I meet his wife so that she could also view me as a new friend or golfing buddy. We're going to try to meet this Friday at the gym and i will have him over "for coffee" after our workout! Diane will be at work and it will be just the two of us. i'm a little nervous, hoping that everything goes just right!
6/11/12
A Boy and his Bra
i can't say for sure, but i probably have a greater fascination with bras than most crossdressers. It hasn't always been that way. Like most cd's or tv's growing up, panties were the object of my desire and the easiest things to sneak away and even wear on rare occasions!
i remember sneaking my sister's bra out of her drawer when no one was home and discovering how difficult it was to put on. By the time i had the courage to try and wear it, my sister had graduated from training bras and the larger cup sizes had me fantasizing about what it would feel like to have small budding breasts! Later, during one of my more daring "searches" i came across an older white training bra of hers and decided to see if she would miss it. i hid it in a secret hiding place in the attic and no one ever found out about it.
i've also written about how i've become rather skilled at putting on a bra as well as taking it off. These two posts (here and here) discuss the progress i've made in large part because of Diane's insistence that i practice. Since then, Diane's also mentioned what appears to her to be my infatuation with brassieres. Yesterday, She stated that She wants me to wear one all the time while i'm at home, and to start going out in public with one as much as possible. "Doesn't it make you feel more feminine" She asked me? It certainly does.
The brassiere isn't something that remains out of sight as easily as so many other items of feminine clothing. Panties, pantyhose, thigh highs, even corsets can be worn much more discreetly than a bra. In addition, the tightness of a bra around your chest is a feeling that is with you the entire time it's on. It's hard to forget you're wearing it.
Late yesterday afternoon, Diane decided that it was time to get intimate and sent me upstairs to get a few things ready. i was to strip down to just my bra and nothing else and get her strap-on ready. Once the strap-on was secured onto Her, She also was wearing nothing but Her own bra. After the foreplay, i found myself on all fours with Diane behind me, teasing me with the tip of Her rubber cock while She gently touched my bra.
Once She was firmly inside of me and stroking back and forth, She ran Her hands over the straps of my bra, even snapping them back in a teasing sort of way. "You love wearing a bra don't you sissy?" She asked me as She leaned over and stroked me. i came instantly, once again exhibiting little if any self control. It was an awesome feeling!
read more
i remember sneaking my sister's bra out of her drawer when no one was home and discovering how difficult it was to put on. By the time i had the courage to try and wear it, my sister had graduated from training bras and the larger cup sizes had me fantasizing about what it would feel like to have small budding breasts! Later, during one of my more daring "searches" i came across an older white training bra of hers and decided to see if she would miss it. i hid it in a secret hiding place in the attic and no one ever found out about it.
The brassiere isn't something that remains out of sight as easily as so many other items of feminine clothing. Panties, pantyhose, thigh highs, even corsets can be worn much more discreetly than a bra. In addition, the tightness of a bra around your chest is a feeling that is with you the entire time it's on. It's hard to forget you're wearing it.
Late yesterday afternoon, Diane decided that it was time to get intimate and sent me upstairs to get a few things ready. i was to strip down to just my bra and nothing else and get her strap-on ready. Once the strap-on was secured onto Her, She also was wearing nothing but Her own bra. After the foreplay, i found myself on all fours with Diane behind me, teasing me with the tip of Her rubber cock while She gently touched my bra.
Once She was firmly inside of me and stroking back and forth, She ran Her hands over the straps of my bra, even snapping them back in a teasing sort of way. "You love wearing a bra don't you sissy?" She asked me as She leaned over and stroked me. i came instantly, once again exhibiting little if any self control. It was an awesome feeling!
6/10/12
A Picky Sissy
Friday's golf date with Jake went very well overall. Rather than stop for a cold drink at the "19th hole", we came to our place where Jake had a beer and the opportunity to meet Diane. In addition to finding him very handsome, Diane also thought he was a nice guy and gave me Her approval to move forward. That little meeting between the three of us was totally vanilla, with no indications by anyone about the underlying relationships that exist, or will exist. That's just the way Diane wanted it to be.
The golf game was interesting. Since we were a twosome, we were paired with a husband and wife who played the first nine with us. Although that limited our ability to converse openly much of the time, i found it almost prophetic that here i was playing golf with a man who i fantasized would treat me like a "wife" someday, and we were paired with another husband and wife. i don't know, but i bet i was wearing prettier panties than Cindy (the woman we played with).
i was alone with Jake for the second nine holes and we got a chance to talk much more openly. Discussing fantasies and fetishes is difficult with someone you haven't known for very long. Even long time partners might find it awkward for fear of rejection or ridicule. So, i was careful about what i mentioned and how i brought things up.
The bottom line is that Jay is "perfectly fine" with my feminine side. He also said that he really only has an interest in "a man who would be willing to be submissive." Both those things sound wonderful and would seek that everything is on the right track. However, i've had this nagging feeling all weekend that Jake is just "fine" with my dressing and being femme, but not as excited about it as i am. i wanted my femininity to be something he really, really, really wanted. In a perfect world, i'd be exactly what he was looking for: a secret sissy wife, one who would be as feminine as possible for him. i know it's not a perfect world and i'm probably being picky, but i was hoping for some unbridled enthusiasm from him about the whole femme thing.
There was one positive sign about it though. After one of my errant drives into the edge of the woods and while looking for my ball, Jake did ask me what kind of panties i had worn that day. When i told him about the pink polka dotted ones, he asked if he could catch a peek at them. With no one around, i obliged and showed him the panties. "Wow!" was all he said.
After i hit my shot from the woods back out into the fairway, i hopped into the cart with him. The late afternoon heat made the course mostly empty. He took my hand and put it over his crotch. His cock was at least semi-erect. "I want you to wear those panties the next time we're together" he told me. That made me hard as well. i hope he wants me to wear more than just the panties!
read more
The golf game was interesting. Since we were a twosome, we were paired with a husband and wife who played the first nine with us. Although that limited our ability to converse openly much of the time, i found it almost prophetic that here i was playing golf with a man who i fantasized would treat me like a "wife" someday, and we were paired with another husband and wife. i don't know, but i bet i was wearing prettier panties than Cindy (the woman we played with).
i was alone with Jake for the second nine holes and we got a chance to talk much more openly. Discussing fantasies and fetishes is difficult with someone you haven't known for very long. Even long time partners might find it awkward for fear of rejection or ridicule. So, i was careful about what i mentioned and how i brought things up.
The bottom line is that Jay is "perfectly fine" with my feminine side. He also said that he really only has an interest in "a man who would be willing to be submissive." Both those things sound wonderful and would seek that everything is on the right track. However, i've had this nagging feeling all weekend that Jake is just "fine" with my dressing and being femme, but not as excited about it as i am. i wanted my femininity to be something he really, really, really wanted. In a perfect world, i'd be exactly what he was looking for: a secret sissy wife, one who would be as feminine as possible for him. i know it's not a perfect world and i'm probably being picky, but i was hoping for some unbridled enthusiasm from him about the whole femme thing.
There was one positive sign about it though. After one of my errant drives into the edge of the woods and while looking for my ball, Jake did ask me what kind of panties i had worn that day. When i told him about the pink polka dotted ones, he asked if he could catch a peek at them. With no one around, i obliged and showed him the panties. "Wow!" was all he said.
After i hit my shot from the woods back out into the fairway, i hopped into the cart with him. The late afternoon heat made the course mostly empty. He took my hand and put it over his crotch. His cock was at least semi-erect. "I want you to wear those panties the next time we're together" he told me. That made me hard as well. i hope he wants me to wear more than just the panties!
6/8/12
Golfing Panties
Guess what i'm wearing for my golf date with Jake today?
i chose the pink one's of course. And just the panties. i don't want to overdo it!
And the best part is that they are a gift from Diane! That's right, she bought each of us a bra and panty set. Her's is the grey one with pink bows. She knows how much i love polka dots and bows. i'm so excited.
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And the best part is that they are a gift from Diane! That's right, she bought each of us a bra and panty set. Her's is the grey one with pink bows. She knows how much i love polka dots and bows. i'm so excited.
6/6/12
Girlie Stuff
i had to be away for a couple of days because of my part-time consulting commitment, but that doesn't mean I didn't have time to fantasize about Jake and a few other sissy things. Unfortunately for Diane however, she's not going to be seeing Brian until next week. Brian's absence has her really looking forward to their meeting and taking steps to make sure everything goes well. i've already been forewarned to make my self disappear next Wednesday afternoon and evening so they can have time together!
i've written a few times about the "art" of dressing in a feminine manner, not just in terms of what you're wearing, but how you put things on and take them off. Learning how to put a bra on and fastening it was one of the things i had a difficult time with but thanks to Diane's insistence on my practicing it over and over, it's now second nature. Another thing that's important is how to put panties on and take them off in a feminine way. This photo shows a woman who is very elegantly slipping her panties either on or off. The legs are kept close together rather than the knees bent up and trying to shove a leg through the right opening! When sliding panties on, i always bend my right leg at the knee but bring it straight up, holding the panties directly in front of me until i can slide my foot through the leg opening. It's much more ladylike!
With the economy teetering on another recession and unemployment a persistent problem, most people fear hearing the term "pink slip." i tend to have different thoughts when hearing it! The slip as a woman's undergarment seems to be a rapidly disappearing thing. i always found my mother's and sisters' slips to be so elegant and pretty. Diane has some but i doubt she wears them very often. i have a few of my own but they're ones i bought many years ago. Of course, my favorite is the pink slip with lace on the bodice and around the hem. Remember the old saying "Pssst, your slip is showing"???? i also remember my sister owning a half slip with the panties built in! It was a pastel green with lace scalloped lace around the edges. That particular item provided me with fodder for many a masturbation session!
The background in this photo isn't the sexiest (looks like some pretty primitive office setting) but the look of that woman with beautiful legs dangling her shoe off her foot is to die for! i think it is so damn sexy. i've seen women do it and even Diane has done it from time to time. i always thought that it was a very deliberate and coquettish move by the woman, fully cognizant that she either had or would quickly get the attention of any males around. It's also a pretty suggestive pose and act in my opinion. i asked Diane once about it and she thought my ideas were silly, saying that most of the time she does it without even thinking about it. Then, she finally admitted that once she noticed that it got some men's attention, she sort of liked it. Just one more thing i should practice!
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6/3/12
Feeling Femme with Jake
In most respects my coffee date with Jake went much better than i thought it would. Looking back, i was probably more nervous than i needed to be, but i think being on edge and nervous makes me more careful and in situations like this, i think that's important. When i think back about the comments Jake's made at the gym and in past conversations, i shouldn't have been as anxious as i was. i'm glad it's finally over!
We talked for more than two hours and about halfway through our time together, i found the right time to bring up my feminine side and desires. By that time we had discussed likes, dislikes and fantasies enough to determine that Jake was much more inclined to being dominant and i submissive. i finally went out on a limb carefully and asked him if he would mind if i wore panties for him. That question opened the door and led our conversation in exactly the direction i was hoping for.
Jake paused and looked me right in the eyes and said "I'd like that. I might even insist on it."
The second part of his comment did catch me by surprise and he could tell. The way he said it turned me on as well. i didn't say anything and after getting over a tinge of embarrassment, smiled back at him.
"Are you wearing panties now?" he asked me. i told him i was and he proceeded to ask me what color they were. i told him they were white and he asked if that was my favorite color. "Not really. i just thought it would be easier for me to slip white ones on at the gym" i told him and let out a nervous laugh.
"Next time wear something a little more feminine" he told me. There was a smile on his face but there was no doubting his seriousness. i got that submissive feeling once again and enjoyed it.
The most awkward part of the conversation came when i told him i wanted my wife to meet him as a friend of mine so that i would be able to establish a "cover" for getting together with him and not raise suspicions. Initially, i thought i would have a hard time convincing him of this because he seemed to be reluctant to do it. Finally, he agreed it might be a good idea. It was awkward for a couple of moments, but at least now i've set it up so that Diane will be able to meet him and hopefully give me permission to move forward. i told Jake that they'd already met at the gym and this would just reinforce our being friends.
Our next date is supposed to be later this week. We're going to get together for a late afternoon round of golf. The plan is for Jake to pick me up and drop me off after the golf when he'll get a chance to meet Diane.
i know this all sounds very complex, but good things take a lot of work most of the time. This time, i'm hoping it's worth the effort.
read more
We talked for more than two hours and about halfway through our time together, i found the right time to bring up my feminine side and desires. By that time we had discussed likes, dislikes and fantasies enough to determine that Jake was much more inclined to being dominant and i submissive. i finally went out on a limb carefully and asked him if he would mind if i wore panties for him. That question opened the door and led our conversation in exactly the direction i was hoping for.
Jake paused and looked me right in the eyes and said "I'd like that. I might even insist on it."
The second part of his comment did catch me by surprise and he could tell. The way he said it turned me on as well. i didn't say anything and after getting over a tinge of embarrassment, smiled back at him.
"Are you wearing panties now?" he asked me. i told him i was and he proceeded to ask me what color they were. i told him they were white and he asked if that was my favorite color. "Not really. i just thought it would be easier for me to slip white ones on at the gym" i told him and let out a nervous laugh.
"Next time wear something a little more feminine" he told me. There was a smile on his face but there was no doubting his seriousness. i got that submissive feeling once again and enjoyed it.
The most awkward part of the conversation came when i told him i wanted my wife to meet him as a friend of mine so that i would be able to establish a "cover" for getting together with him and not raise suspicions. Initially, i thought i would have a hard time convincing him of this because he seemed to be reluctant to do it. Finally, he agreed it might be a good idea. It was awkward for a couple of moments, but at least now i've set it up so that Diane will be able to meet him and hopefully give me permission to move forward. i told Jake that they'd already met at the gym and this would just reinforce our being friends.
Our next date is supposed to be later this week. We're going to get together for a late afternoon round of golf. The plan is for Jake to pick me up and drop me off after the golf when he'll get a chance to meet Diane.
i know this all sounds very complex, but good things take a lot of work most of the time. This time, i'm hoping it's worth the effort.
6/1/12
A Tennis Date?
i'm on my way to the gym to meet Jake and really looking forward to our coffee date after. If it were up to me, i'd skip the gym and maybe even the coffee date! i'm just kidding, but our phone conversations have gone very, very well and i'm becoming much more comfortable with sharing things with jake. i'm not quite where i want to be and haven't discussed my dressing femme for him, but all indications are that when i do, he'll be very open to it.
i also discovered that he enjoys golf and tennis. i still golf and used to play tennis regularly. It's been some time but i'd love to start playing again with Jake. We talked about how having other things in common are important as well. Having a friend to enjoy sports with is a great way to provide a "cover" for the wives! Not that i need one since i will be doing this with Diane's permission after her final approval of Jake.
Anyway, the thought of playing tennis with him had me fantasizing again this morning. i always found tennis dresses, particularly the old fashioned ones, especially sexy and feminine. No wonder Renee Richards finally made the decision to live full time as a female! Just imagine how fun it would be playing tennis dressed in this cute little outfit! i'm sure i'd be guilty of more than a few "double faults."
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Anyway, the thought of playing tennis with him had me fantasizing again this morning. i always found tennis dresses, particularly the old fashioned ones, especially sexy and feminine. No wonder Renee Richards finally made the decision to live full time as a female! Just imagine how fun it would be playing tennis dressed in this cute little outfit! i'm sure i'd be guilty of more than a few "double faults."
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