The Office Sissy

i just returned home from dropping Jake off at the airport today.  He closed his firm at noon today, giving everyone the rest of the week off and had asked me if i could drive him to the airport.  i agreed and he told me to come on up to his office around 11:30 this morning. 

"Wear something pretty under you clothing.  It's time we play out that fantasy I told you about" he said. 

The fantasy?  my sucking his cock while he sat at his desk.

i was nervous all morning.  He not only insisted on something pretty, but i had to be wearing a bra.  i arrived at his office in stockings, garter, panties and a bra.  The bra was easily concealed under my shirt and jacket. 

His administrative assistant let me in to see him and it was evident she was getting ready to leave soon.  He told me to have a seat and take my jacked off.  "i prefer to keep it on i said" in a joking manner, a little concerned that Jackie, the administrative assistant would walk in and possibly see my bra or bra straps through my shirt.  "I said take it off" he said  in a stern manner.  i laid it over one of the chairs in front of his desk as sat in the other.

Jake made a couple of calls, both of them on speaker phone.  During the first call he walked over behind me and ran his hands over my chest.  It was more to feel if i was wearing the bra than any affectionate touching.  When he felt it i could tell he was pleased that i had obeyed, the groping turned into a softer touching with his fingers running along the outline of the straps as he continued to talk on the phone. 

As expected, Jackie did come in to announce that she was leaving for the day and wished Jake a Happy Thanksgiving.  Jackie, a very efficient looking 50-something year old woman, looked very nice in a greyish pinstripe business suit, white blouse and heels.  Jake saw me looking her over.  When she was gone, he said "I bet you'd like to be my secretary wouldn't you?"  We both laughed.

He then went over and locked the door.  "Show me what you're wearing" he said.  "Don't be nervous.  There's nobody left here.  Trust me."  With the door locked, i felt somewhat safe and began to strip. 
"All the boy clothes off" he ordered.  "Model for me" he said.  i slowly turned around to show him my lingerie.  My cock strained in the chastity belt.  It would strain for long time.

Jake dialed the phone and began to talk to a client in Wilmington Delaware, almost ignoring me while motioning that i stand next to him.  He sat there, rubbing my ass through the panties as he talked on the speaker phone.  He stood up and motioned to his crotch, indicating that he wanted me to loosen his trousers and start with his cock.  i did.

Soon, i was kneeling in front of him and kissing his crotch, balls, and cock.  He was put on hold briefly by the client during which time he had ma take his shoes and slacks off.  He stood before me and told me to start sucking him.  He finished the conversation in that position, wishing his client a Happy Thanksgiving and promising to touch base with him next week. 

There was one more call that lasted only 5 minutes or so.  I had his cock in my mouth the entire time, sucking but also trying to be quite with my slurps, kisses and licks.  By the time he hung up, he was rock hard. 

"Ready for a big load?" he asked.  i sucked and nodded at the same time.  "Beg for it."

"Please Daddy" i said in my softest and sexiest voice, looking up into his eyes. 

"No mess on the floor.  Promise?" he asked. 

"Yes Daddy, i promise." i said.

He grabbed the sides of my head and thrusted back and forth.  He went deep into my throat and i gagged several times, and i was careful that i caught the saliva mixed with precum that was dripping down my chin with my hands. 

Jake was farm more aggressive than usual - "I love it when you gag on my cock" he said passionately and immediately shoving it in deeper, causing another gagging reaction. 

"Ready?" he asked and without waiting for an answer shouted out "Here you go sissy!" 

Typically he enjoys cumming all over my face but not this time.  He did his best to stay in my mouth and i did mine to keep him there.  It was a totally different sensation, large spurts of his semen hitting the back of my throat and filling my mouth, only a small portion finding its way to my lips. 

i was proud, i don't think i spilled a drop.

We came down from our high, got dressed and made our way to the airport.  Naturally, there was no good bye kiss.  Instead, there was a slight caress of my thigh, with a "love tap" on my CB-3000.

"Be a good girl while I'm gone" he said as we pulled up to the curb.  "Some day, I'd like to have you bent over my desk.  Would you enjoy that?"

"Yes Daddy, i would" i said with a very content smile on my face.

It was a very, very, very sexy and gurly afternoon!

love,

sissy terri

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Submissive Pleasures

i was planning on spending a few hours with Jake here on Friday afternoon.  He was taking the afternoon off and was going to stop by before heading to his son's baseball game at 4:30 PM.  i was all dressed and ready to greet him by around noon time when he called to tell me that he was going to be late.  i was mildly disappointed, but at least the afternoon wasn't completely cancelled.

i waited patiently for what turned out to be more than three hours.  During that time, Jake texted me several times letting me know that he was in a meeting (one that he called by the way) and that he would be here to see me as soon as he could.

The waiting for him to arrive made me feel very submissive.  i knew that the longer i waited, the shorter our time together would be.  As the afternoon wore on, it became apparent that if he came at all, it was going to be for a real "quickie."  The final text i got came at 2:33 PM - "Leaving now.  Get ready for my cock."

i waited before i responded.  i was upset that he himself had scheduled a meeting knowing that i was waiting for him.  i didn't know the circumstances and i'm sure he had a good reason, but it made me feel used.  However, all the things that upset me and the negative feelings were minimized by the powerful submission i felt.  i texted Jake back with a simple "Yes Sir."  It was the first time i used that term in a text with him.

Jake called when he was minutes away and told me to be on my knees waiting for him.  It was about 3:30.  i knew he'd have to leave by 3:45 to be on time for his son's game.  We'd have about ten minutes.

Jake arrived at 3:35 and left just before 4 PM.  i had time to pleasure him twice.  Not once did i think about my own pleasure in the form of an orgasm, my submission was so strong and the feeling itself was pleasure enough for me.

Jake was especially dominant, wasting no time in telling me to take his cock into my mouth.  He held my head in place with both of his strong hands and made sure that i swallowed everything when he came the first time.  There was quite a bit, and I gagged several times.  i think my gagging made him even hornier.

His second orgasm took a little longer but was just as satisfying; to both of us.  He pulled out and came all over my face.  His warm semen felt wonderful, so did licking it off his fingers when he was finished cumming.

Before i knew it, he was putting his pants on and looking at his watch.  He apologized for being so rushed, and told me he would make it up to me.  Before he left he told me how awesome i was today.  "A real good girl" was what he called me.

He thanked me and was out the door on the way to his son's game.  When he thanked me i said "You're welcome" just out of habit.  i should have actually thanked him for making me feel the way i did.

love,

sissy terri

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Sharing Fantasies

It's taken a little time but both Jake and i seem to be more comfortable with sharing some of our kinkier fantasies with each other.  i suppose once a man takes another anally, and similarly once you've given yourself up that way to another man, you don't feel like you've got much to hide.

Yesterday i was on the phone with Jake and we both got each other aroused.  i was telling him how i wished i could be kneeling in front of him with his cock in my mouth and he told me how much he loved it when i did that.  "I love it when you look up at me when you suck me" he said "and when our eyes meet as I'm looking down at you.  Just thinking about it has me real hard.'  i could only let out a sigh of frustration, indicating that i wanted nothing more than to be doing that very thing.

"You know what else i'd like?" he asked.

"Please tell me" i answered him, almost begging.

"Well, you know when I'm laying back on the bed and you're between my legs licking my balls and cock?" he asked me.

"Yes..." i said in anticipation of what was to follow."

"Well....I really love the way you use your tongue on my balls and..." there was a hesitation here, as if he was a little inhibited about what he was going to ask me.  "Well, I'd love it if you'd rim me and lick my ass."

I didn't want to hesitate, for fear that he'd misinterpret it as reluctance on my part.  "Jake, i'd absolutely LOVE to do that for you!" i said like a giddy little girl.

"Really?  You'd like to rim me?  Lick my ass?" he asked.

"God yes.  It's one of my biggest fantasies" I told him.

We both laughed. It was one of his fantasies and one of mine, yet it took this long for us to share it.

"I still want you to start with my cock and balls though" he joked "so that I can see those pretty eyes of yours.  Then when I'm ready, I'll tell you to slide that tongue of yours down to my ass."
 
We talked a little while longer but he had to run.  If the conversation had continued, i'm sure more fantasies would have have been brought up.  We promised to be more open about such things from now on.

i can't wait to see him again.  i want to please him, and fulfill his fantasy. 

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A Sissy Spanking

i had a wonderful afternoon with Jake on Friday.  It was the most relaxed we've been when together since we first met.  Trysts like ours (two married men getting together for sex) are usually accompanied with lots of anxiety and nervousness for obvious reasons.  It's also more difficult for the partner who's going to the other partner's home.  They can't experience the same level of security the other feels.  It's only natural.

Jake was here at our house on Friday afternoon.  His golf clubs for our Friday afternoon game never made it out of the trunk of his car.  Neither did mine.  Instead, we played other types of games.  Diane wasn't due home until around 7 PM and as the afternoon wore on, Jake seemed more and more comfortable.  He was more dominant as well.

Getting ready for his arrival had me in a high state of arousal.  i swear i came close to cumming just thinking about being feminine for him.  i wanted to surprise him , but couldn't decide what to wear to greet him.  i had bought a pretty powder blue babydoll set just like he wanted, but i didn't want to be wearing it right away.  Instead, i laid it out on the bed in a guest bedroom and thought i'd lead him by the hand into the bedroom and slip it on for him.

i changed into some cute white short shorts with pink panties underneath, a white bra and a sleeveless pink blouse.  i also wore a pair of heels, a cute faux pearl necklace, a short wig, light makeup and mascara and a hint of lip gloss. 

However, minutes before he was scheduled to arrive, i changed my mind!  i thought it over and felt he might be expecting me to be wearing the blue babydoll set, so i hurried to make the change.  i'm glad i did.

i answered the door wearing the babydoll pajamas, in heels, makeup, necklace and smiling at him with my pink pouty lips.  i could tell right away that i had pleased him.

"I'm happy you followed directions" he said, "otherwise I would have had to spank you."

He must have sensed a little disappointment in me because he quickly added that "I may decide to give you a sissy spanking anyway."   He immediately put me into femme subspace.

Submissive as i felt, i did take him by the hand and led him into the guest bedroom.  He took me in his arms and held me while he kissed me and told me to get him undressed.  With my clit throbbing n my panties, i tried to take my time while i undressed him, but wanted him naked quickly.  i kissed his chest when i took off his shirt.  i stroked and kissed his thighs when his pants came down.  i buried my face in his crotch and kissed his cock when i slid down his briefs.

He pushed me down on the bed and lay on top of me.  i wrapped my smooth legs around me as i felt his strong muscled chest against my smooth bosom.  "Soon, I hope you're ready to let me take you like a woman" he said.  i felt my heart flutter.  i was stunned.  Nervous and unsure about what to say, i waited a little and said "i'd love that."   Before i could say anything else, his massive cock was parting my lips.

We spent the afternoon in bed, talking in between bouts of sex.   There was also a little modeling for him.  When i told him how i had changed my mind about what to wear to greet him, he told me to put the original outfit on for him.  He liked it.  It's the outfit i wore for my spanking.

It's not the first time i found myself over a man's lap.  Ken had spanked me before but not that often.  Jake got into it.  It was more than a playful spanking.  i loved being told what a naughty girl i was.

When the spanking was over, i proved it by taking his beautiful cock in my mouth and swallowing every drop of his hot and loving cum.

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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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Feminine Feelings & Desires

My feminine feelings and desires go well beyond my crossdressing urges.  Diane knows about my bisexuality as I admitted my desire to be with another man many years ago, even before I was with my first man.  My admission came about for a couple of reasons.  I wanted to be open and honest with her and most importantly, she would often tease me about it in some way when I was dressed or when I was playing the female role in our sex play. 

Once I told her, she asked me if I felt better about telling her.  I told her I was glad I did and hoped that it wouldn't change her love for me.  She reassured me that it wouldn't but also said that she "kind of"knew I had those urges all along.  She said she could tell just by the way I reacted to things she said and how she acted when she took the dominant and aggressive role with me, and how much I enjoyed strap-on play, particularly sucking on her make believe cock before she made love to me.

The discussion led to some "ground rules" about my playing with other men (and there haven't been many.  The rules were pretty simple.  I could only play with married men and there could be no anal sex.  We also agreed that like myself, they would have a high need for discretion, cleanliness and safety.  While she never met them, I would have to get her "approval" before meeting them, giving her whatever details I had about them.  So far it's worked very well even though I haven't been with a man in nearly a year.  The last man I had "an affair" with retired and moved away.  I'm picky, and haven't found anyone since.

This brings me to one of the moods I'm in today.  I feel overly feminine.  I got all dressed today with wig, makeup, heels, etc.  All day, I was craving cock.  I wanted to be on my knees in front of a man.  I wanted to look up into his eyes and beg for his cock.  I wanted him to make me beg.  I wanted him to tease me with his cock, slap my face with it, run his cock's head over my lips, over my eyes, nose and entire face.  When he finally let me put his cock into my mouth, I wanted him to fuck my face hard, make me gag, see the saliva dribble down my chin, call me names and shove his cock deep down my throat.

When he was ready and had fucked my face enough, I wanted him to splatter his cum all over my face and into my mouth.  I wanted to look up at him with my face covered with his juices, marked like his sissy bitch.  He might even scoop up the cum with his fingers and feed it to me. 

I would be there for his satisfaction.  There would be no sexual release for me, but my feminine needs and desires would have been met. 

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Sucking Cock in Panties

The panties shown on the left under my "Daily sissy Stuff" section are similar to the one's I wore the first time I sucked a man's cock.  I was on business in a city a few hours away from home and had finally decided to meet "Rob."  He was a married retired man and was home during the week while his wife worked.  He also drove a Harley.  He wasn't a nasty biker, member of a gang or anything, but the fact that he rode a Harley sort of turned me on.

I was wearing a business suit that day but had those pretty white panties on underneath with lovely lace all over my smooth bottom.  Rob just loved the panties!  "As sexy as anything my wife has" he told me.  They got him aroused, and most importantly, they put me in the mood to suck my first ever cock. 

Lingerie and other type of women's clothing all help to make a sissy feel for feminine.  But so does a warm load of cum shot all over your face.  Paired with the panties, it was the most femme feeling I'd had in my life to that point. 

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