Diane's Decision - Chastity

A few weeks ago i wrote that Jake, the man i had an affair with a while back, had contacted me again and wanted to reestablish our relationship.  This time, Jake seems far more interested in taking on a more dominant role than he did before, something i also wanted.  However, i needed Diane's permission to see Jake again.  i discussed it with Her and She told me She would think it over and decide.  

i followed this up with a post called "The Sissy Waiting Game" where i wrote: "Diane hasn't yet given me permission to get together with Jake.  This morning She assured me Her decision was imminent.  "Don't be so impatient" She said with a laugh.  i have the feeling She is going to let me see Jake.  At least that's how She's acting.  She just seems to be enjoying the "waiting game" She's making me play.

After that post, i didn't put anything up here for a week.  When i finally wrote again i explained my silence by letting everyone know that i had some things to sort out in my life and how i wanted to proceed.  i'm ready now to let you know what led to the silence and what i've decided.

Diane did give me permission to see Jake.  From the way She was acting i thought She would, but i also thought She was simply enjoying the control She had over me and the fact that She could make me wait while She took all the time She wanted to make Her decision.  Her decision however came with a catch.  The condition She put upon my seeing Jake took me completely by surprise.  It was something She'd previously expressed no interest in.

"You can see Jake" Diane said.  i immediately thanked Her but was quickly interrupted.  "I'm not finished.  There's a condition attached to my decision.  If you're going to see him, you're going to be wearing a chastity belt when you do."

"What?  i'm not sure what You mean." i stammered.  Diane had usually discounted chastity as a means of expressing Her dominance.  i'd brought it up several years ago and whenever the topic came up She dismissed it immediately, saying the whole process or lifestyle was simply "too much work."  She would also say that She knew i masturbated and it didn't bother Her that i did.

"That's my decision" She continued.  "I ordered a chastity belt and it should be here in a couple of days.  If you're with Jake, you're in chastity.  Besides, isn't it a fantasy of yours?"

i suppose it is.  It was then that i remembered having a discussion with Diane and Her teasing me about locking me up while i was home alone.  i wrote a post about it and finished the post writing about what it might feel like to be locked up while with a man of my own.  Diane doesn't comment much about my posts, but it's clear that She had read this one and filed it away.  

The chastity belt arrived as scheduled and i've been wearing it regularly, beginning with only a few hours and working my way up to most of the day after about 10 days.  It's not as uncomfortable as i thought it would be, but i haven't yet been made to wear it at night.  It's a  CB-3000 pink package  from A.L. Enterprises.

i want to see Jake but haven't yet got back to him to let him know i'm "available."  If i do, i'll have to explain to him that i'll be in chastity and that will no doubt lead to an explanation on my part that will reveal far more about my relationship with Diane than he already knows. 

The fact that Diane decided to have me in any type of chastity is not the only thing that's surprised me about this whole thing.  i'm also very surprised that Diane is prepared to have me share this part of our life with Jake.  She knows Jake, but not in an way that She'd want me to share such intimate details of Her dominance over me.  

i'm going to call Jake early this week.  i want to be with him again, and i think he'll understand.  His only contact with my cock has been fondling it through my panties and seeing me masturbate in front of him after providing him with pleasure.  The fact that it would be locked up while i serve him shouldn't be an issue as far as that concerned.  i'm hoping that perhaps, he might even be aroused by it.  i would think that some Dominant men would enjoy having a chastised sissy to use.  We'll see,

Once again, Diane's exerted Her control in an a way i never thought She would. 

love,

sissy terri

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The Sissy Waiting Game

It's been a weekend of "waiting."  Waiting is a pretty common activity for submissives i would say.  i did plenty of it this weekend and am still doing it.

Diane took advantage of my absence on Saturday to schedule a date with Paul at their usual location:  our house and bedroom.  It's not that She needs my permission or has to wait for me to be away to invite Paul over, it's just that She knew i'd be gone for most of the day.

i played in a charity golf tournament that had an 8 AM shotgun start.  It was a four-man scramble with a total of 144 golfers; two teams on every hole.  If you've played in something like that you know it's going to be a long round.  It also included lunch, door prizes, raffles, etc.  i wasn't ready to leave until close to 3 PM.  Problem was, i hadn't received Diane's permission to return home yet.

i stayed at the club, showered (careful not to reveal my panties in what was fortunately for me a deserted locker room), watched some college football in the bar area and waited for a text from Diane.  It came a little bit after 4.  "Hurry home" is all it said.  No more than twenty minutes later i was down between Her thighs, completing the obligatory cuckold cleaning that happens after the lover's gone.  my own pleasure had to wait until Diane was totally pleased, both sexually and with my cleanup of Her privates.

There's also another piece of waiting going on.  Diane hasn't yet given me permission to get together with Jake.  This morning She assured me Her decision was imminent.  "Don't be so impatient" She said with a laugh.  i have he feeling She is going to let me see Jake.  At least that's how She's acting.  She just seems to be enjoying the "waiting game" She's making me play.

In the meantime, Jake's been peppering me with saucy and sexy emails, hinting that he can't wait to have me put a lovely lipstick ring on his cock!  Those type of things drive me crazy and test my patience.  He's also hinted at some spankings, light bondage and even more.  i hope Diane's decision comes soon....very soon.

Here's a collection of very pretty panties i just re-posted on my tumblr page.  Think Jake would like to see me in some of these?  i know i'd love wearing them :)

love,

sissy terri

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My Bisexual Sissy Urges

It's been months since i've been with a man but my bisexual urges and fantasies haven't lessened at all.  If you recall, Diane decided that She didn't want me to be having an "affair" with Jake or any other man.  When that happened back in February, i was growing frustrated with Jake and his "on again off again" need for bi sex.  When he was in the mood it was very good.  When he wasn't, i wouldn't hear from him for weeks.

Just prior to Diane's decision i was also corresponding with a man named Howard.  He seemed like a great guy and the type of Dom i was looking for.  Unfortunately, i couldn't proceed with Howard and told him so.  i even told him why.  Howard thought i was a very lucky submissive. 

A couple of weeks ago, Jake contacted me again via email and asked me to give him a call.  i used to see him at the gym once and awhile but i hadn't seem him there in months either.  i was reluctant to call him and procrastinated about it.  i decided i would but thought it best that i let Diane know first.  She had no objection to my calling him in response to his email.

i talked to Jake for more than an hour when i finally called.  A couple of things have changed in his life, giving him more free time to play golf and do other things.  And naturally, once again he's interested in meeting with me like we used to with assurances that this time it would be different.  He says he's had the urge for awhile, and it's not going away this time.  i have reason to be doubtful but, i also have reason to want to give it another try....if only i could.  "Let me think it over" is how i left it.  However, we both left the conversation very aroused.  He certainly knows how to make me feel sissy and femme when he wants to.

i talked to Diane about our conversation and Jake's request.  "Are you asking for permission to see him?" She asked.  i told Her i wasn't sure, but that if i wanted to, knew that i would need Her permission.  She told me to let Her know when i decided what i wanted to do.

We had a follow up discussion about it last night and i told Her that i'd like to give it another try with Jake and asked for permission.  i wasn't totally surprised that She said "yes" though i was certainly prepared for a "no" answer.  But with Diane, nothing is as simple as it seems.  She's going to allow me to see Jake, but not just yet.  "I'll let you know when you can start seeing him" is what She told me.  In the meantime, i'm supposed to tell him i'm still mulling it over if he asks. 

i don't know how long Diane is going to make me wait, nor do i know why She's doing so.  If i didn't have to wait, i would probably call Jake and invite him over today.  i'm home alone and would dress in anything he wanted.  i'm aching to please him. 

i'm hoping that he's going to be as dominant and as charming as he sounded on the phone when we talked.  i know he can be.  i want to feel his hands roaming over me.  i want him to put me over his lap and spank me.  i want to drop to my knees and please him.   My list of wants is long, very long.

i hope Diane doesn't make me wait too long.

love,

sissy terri

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Deeper Submission, Cuckolding & Daddy's Little Girl

This may sound so silly to my readers - if i still have any left after not posting in so long - but i've been a little anxious about posting.  i have so much that i want to share and that's part of the problem.  The length of time between posts causes this, but so do the emotional swings i'm going through.  i'll do my best to get my feelings "out there" and hope you all understand.

Diane has fully embraced Her dominant role in our marriage, something that i never thought would happen when all of this first started.  i can honestly say that She is now far more dominant than i ever imagined She'd be, and it often goes further than i want it to.  She's come to the conclusion that it's what She wants, and knows She can have it. 

Diane's quest to find a lover took a break while we were on vacation for a little more than two weeks.  She continued to correspond a little with the three men She had decided were worth pursuing, but during that correspondence, She realized that only one was the type of man She was looking for.  During this time, She also shared with me that there was another man.  It was someone She worked with and they'd exchanged a few casual flirtatious remarks.  They have a lunch date scheduled next week. 

When we returned from vacation, Diane had a meeting with the lone gentleman from Her initial search and it was a huge disappointment.  He misrepresented his physical description for starters.  Diane wanted someone at least 5'11" or taller.  His claim that he was 6'0" was an obvious lie.  Less obvious was his misstating his professional status.  There was no attraction whatsoever. 

Diane's new potential lover does pose a few minor problems.  For starters, it's never a good idea to mix work with any type of romance.  However, the nature of their profession and the difference in their positions makes it a bit easier.   The other issue is that Diane and I both had the same profession, only in different fields, and I know this man.  He's not a close friend but we do know one another.  He's younger than the both of us, very good looking and masculine and it's obvious why a woman would be attracted to him.  He's also married. 

Diane definitely has a physical attraction to "Paul" and knows that he has one for Her.  Last week She told me that She's not going to insist that Paul agree to full blown cuckolding like She insisted upon with other suitors.  Instead, if he needs reassurance, She's going to tell him about our "arrangement."  Not all of it, but basically that She can have a lover if She wants.  In Her opinion, if Paul is into the whole cuckolding thing, then it's "a bonus."

My ultimate cuckold fantasies of being present when another man makes love to my wife and all the different things that can take place may never be realized.  That's not necessarily a bad thing.  i'm having a difficult time accepting some aspects of my increasingly submissive role in my marriage, so i'm sure i'd have a more difficult time with the extreme cuckolding.

i'm also seeing Jake again and that's fulfilling my bisexual and feminine needs.  He's become a bit more aggressive with me and i wonder if that will continue and if so, how far he wants to go.  The last time we were together he really enjoyed calling me "Daddy's little girl" while i sucked him.  i loved it.

i'll try to post more often.  Promise.

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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Repressing My Sissy Urges

Earlier this week i got an email from Jake, then a phone call.  i didn't answer the email right away although it was my intention to do so, so a few hours later he called me.  There was some small talk and he asked me how i was doing, how the holidays were and so on.  i had a feeling i knew why he was calling and sure enough, he asked me if i'd like to get together with him again.

The honest answer would have been a "yes."  The more difficult one was to say no.  Luckily i had thought this through before and anticipated that he would contact me again at some point.  To be honest, i'd even thought about getting in touch with him but i didn't.  Jake had often told me that his desires to be with another man, to have someone orally please him without any reciprocation, would come and go.  There were periods where the desire was so intense according to him, and other times when it would wane and be almost non-existent.

It made me feel so "used" and inferior.  i felt like i was his little toy to be used during one of his needy periods; someone to be tossed aside when he didn't feel like it anymore.  i didn't only feel like that.  Facing reality, i really was that plaything of his to use until his urges subsided.  The urges are back now, and he wants me on my knees in front of him once again.

Being looked upon that way by another man has its own perverse sort of pleasure for a submissive.  i'd love to feel his cock on my lips and in my mouth once again.  i'd love to dress sexy for him and be told to drop to my knees and pleasure him.  i just can't do it. 

The urge to be a submissive sissy to a man remains.  It was hard to say no, but i'm glad i did.  Maybe i'll change my mind someday, but i doubt it.

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My Sissy Emotions

i want everyone to know that I'm fine.  Funny how you can make friends through this relatively anonymous phenomenon we call blogging.  i haven't posted in a little over two weeks and i've received five emails from blogger friends (all but one of them a submissive sissy like myself) asking if i was okay.  It's quite touching and heartwarming to be totally honest with you.

i've been in some sort of funk.  Diane calls it a "sissy funk" most of the time but She's also said it's my feminine hormones taking over.  No, i'm not taking anything but She tells me that's it's totally understandable that the more i behave and adopt traditional feminine roles and behaviors, the female hormones that do exist in me will become more dominant.

my affair with Jake seems like it could be over.  i wrote last time about how i thought Jake might be headed to one of those "valleys" he referred to at the outset of our relationship.  His bi urges seemed to come in peaks and valleys he said.  But soon after i posted two weeks ago, he called me to say that he thought his wife was getting suspicious, asking him some odd questions.  He felt she might be thinking he was messing around on her and thought it was a good idea to cool it for awhile.  I heard from him a couple times on email since then and saw him at the gym once, but it's been about 10 days since we've communicated.  i understand, but can't help feeling he's just plain lost interest in me.

On the other hand, Diane and Brian see each other very regularly.  Somehow, Brian's been able to arrange his schedule to be in our city at least one night per week over the last month, sometimes two.  Diane's been telling him more and more about my submission to Her.  She tells me that he's fascinated by it and seems turned on that he's her "alpha" lover.  That's the term i'm using not his.  Diane tells me She's very confident now that it's only a matter of time before he "knows everything" and that i'll be cuckolded in their presence.  It's something i fantasize but am also anxious about.

Through all this, Diane's been very understanding and supportive of my feelings.  It seems like when i'm feeling very low, at my lowest points for example, She uses that as an opportunity to exert more dominance over me and exaggerate my femininity.

In those instances, usually after i've completed some humiliating task while dressed in a very sissy-like outfit, we sit and talk about where we are in our marriage and whether or not we're happy with where it's headed.  In spite of the emotional roller coaster i've experienced of late, i have to admit i want it to continue.  Diane insists that "turning back now would be a big mistake."  i have to agree with Her.

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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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Just Like a Woman - My First Time

i got to meet with Jake this week (at his place no less) and it was an intensely sensual and pleasurable meeting.  Jake's wife was gone for a few days staying with her mother and he had the whole house to himself.  There was something very naughty about him taking me into the master bedroom and telling me i was going to be his "wife for the day."

The deep purple short nightgown he bought me as a surprise got me hard instantly.  Jake joked that i certainly didn't look very feminine with my little erection and suggested i do my best to hide it.  It was difficult, but i tucked it between my legs for him while modeling the nightie and he got a laugh out of that.  The black lace on the gown made me feel more sexy than sissy-like and i think Jake felt the same way.  i was soon on my back on the big bed with  my smooth legs wrapped around him as he lay on top of me.  i was swooning and wanted him.

Jake was as hard as i'd ever seen or felt him.  i wanted him in my mouth, but part of me wanted him inside of me even more.  He could tell and said "Do you think you're ready?"  As much as i had been thinking about this moment, it was another one of those things that caught me by surprise.  i wasn't sure what to say and i think he was uncomfortable with the silence and finally told me it was fine if i didn't want to.   But i did want to.

"Can we try?" i asked him.

"Of course.  We can stop anytime" he said as he lay on top of me and stroked my thighs, "just say so."

Well, after plenty of foreplay (really the best part), a large amount of lube, some discomfort, and plenty of tenderness and understanding on Jake's part, i took his beautiful cock in my bottom.

It took awhile before he entered me fully.  In fact, he let me control how deep he went, instructing me to back onto his cock when i felt comfortable enough.  i was on all fours on the bed and i just loved feeling the tip of his cock pressed up against me.  The most difficult part, much like taking Diane's strap-on, was the initial penetration.  i relaxed after awhile and enjoyed it immensely.

Jake used a condom of course, but knowing he came from making love to me that way drove me wild and i had an ograsm of my own, without even touching my own penis.  i felt like i had an orgasm "just like a woman."  In fact, those are the terms Jake used when he told me i was cumming "just like a woman."

When it was all over, i felt different and still do.  It's hard to explain exactly how i feel different.  Part of it is as if i've taken a huge step towards becoming more like a woman, while still retaining my physical masculinity.  There's a huge emotional component to it also.  i seem to feel an inner glow that's difficult to explain, a feeling of fulfillment.  i can't wait to do it again.

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"Marking" a Sissy

This is going to be a very unusual post for me.  With few exceptions, my posts typically avoid graphic sex scenes, explanations or accompanying pictures.  i've always tried to focus on my inner feelings, attempting to express what's going through my mind and how my relationship with Diane affects our lives.

This break from routine is a result of my meeting with Jake yesterday.  We hadn't seen each other in awhile and even thought there wasn't a tremendous amount of pre-meeting planning, it was clear from the time we saw each other that we were both very horny.  i was aching to suck his cock and he was looking to be pleased by me.

i dressed in a short red nightie and some black heels after his phone call that instructed me to wear something sexy.  i told hime that the front door would be unlocked and to come right in and lock it behind him and come upstairs to one of the guest bedrooms where i would be waiting for him.  When i heard the front door open, i decided to stand in what i thought was a seductive pose at the head of the stairs.  My sissy penis was already "tenting" the nightie with excitement.  i also had my dirty blonde wig on and a light touch of makeup.

When Jake got upstairs, he didn't even wait until we got to the bedroom.  Right there in the hallway, he forced me down to my knees and immediately took out his cock, rubbing it all over my face.  i was ordered to keep my mouth closed until he told me otherwise.  He continued to rub his cock all over me as it got bigger and bigger.

Then, he turned very, very dominant.  More dominant than he's ever been with me.

He slapped me with his hard cock.  Hard.  Real hard.  It hurt.

"You're going to suck me like a good girl" he said, "and when I'm ready I'm going to officially mark you as my sissy."

The words almost made me cum.  If i had been stroking myself, i'm sure i would have.  "....officially mark you as my sissy.."  i loved it.

"Now suck me" he ordered, and i obeyed.  i'd never felt more submissive, sexy or feminine.  All i wanted to do was please him.  i felt like his sissy, his slave, his bitch.  i couldn't wait for him to cum.  He talked dirty to me.  He held my head in place.  He pumped back and forth and there were several times that he made me gag.  i loved it all.  Then he slowed down and told me what a good girl i was.

i knew he was going to cum soon and couldn't wait to feel his cum all over my face and to taste it.  He took his cock out of my mouth and told me to close my mouth and eyes.  I looked up at him, closed my eyes and obeyed, waiting for his warm manjuice.  He unloaded on me....big time.

Jake's given me facials before, but this one was the best.  When it was over, he told me not to move and keep my eyes closed.  He wanted to admire his handiwork.  Again, the feeling of his cum on my face, his 'official mark', was a feeling i will never, ever forget.

When i was told to open my eyes, Jake used his fingers to scoop up his sperm and feed it to me.  i licked his fingers eagerly, making sure i got every drop.  He called me "a hungry little girl."  i was, but i was horny as well.  He knew that.  When i was done, he let me masturbate in front of him....like a sissy.

i guess it's official now.  i belong to Diane, but i'm also marked as Jake's sissy. 

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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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Looking for Panties

A busy week came to a difficult end yesterday. i wrote several times about a previous bi relationship i had with Ken until he moved away, and how i was looking forward to seeing him when he visited this summer.  That was before i met Jake and i just wouldn't have felt right playing with Ken while being involved with Jake.

i had lunch with Ken yesterday even though i had told him i didn't want to play.  We had plenty of intimate and fun times together and are still friends.  It was a difficult lunch.  He told me how disappointed he was that we couldn't play together while he was here and left the door open if i wanted to do so.  i'm not going to change my mind.  When i played with Ken, he was the only man i was involved with.  That was our agreement.  He understands and we're still friends and i have to say that he still makes me horny.

Things seem to take more time with Jake than they did with Ken when it comes to expressing his fantasies openly.  i can understand because i'm the same way.  But we're both making progress.  Yesterday, Jake revealed to me how a certain type of panty really turned him on (not wearing them..lol...but seeing them on me!) and how he'd like me to get a few pairs.  He loves panties that have a seam straight up the back along a woman's ass cheeks.  i'm not sure what you call panties like that and he even sent me a picture of what he meant.

 So now, i'm on the market for panties like that and haven't been able to find many online.  i haven't gone out shopping for them yet either but if any of my readers know where i can find something similar (he would love to see me in a pair of white ones) please let me know.  i'd love to have them for our date next week!

Feel free to leave your suggestions here, or if you prefer send me an email.  Thanks :)

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A Complete Cuckold?

i had to take somewhat of an unexpected business trip this week and haven't been able to post anything on the blog.  i procrastinated in doing so last weekend and then when i found out i had to travel late Sunday, i just ran out of time.  In fact, i'm still away from home and won't be back until tomorrow night. 

There was a time when traveling alone was something i looked forward to because of the opportunity it gave me to fully express my feminine self.  i would bring some lingerie with me, do some shopping and several times i even visited a woman who provided makeovers for crossdressers.  There was no sex involved, but just an entire makeover from head to toe that included makeup, a wig, and just about any type of clothing you could think of.  i used to love my trips to Chicago!

For the most part, that thrill is gone because i have the opportunity to express my feminine self both at home and with Jake.  At home, my role as Diane's wife couldn't be any clearer.  Not only am i expected to do all the things a real wife would do, She goes out of Her way to make sure i know that i'm the wife and She wears the pants in the family.  It's become more pronounced since She and Brian have been seeing each other.

My Friday date with Jake was really nice.  i got to get dressed fully for him at his house despite my nervousness.   It was silly because there was no way anyone was going to be around.  It was the first time i wore a dress, hose, heels and a wig for him.  It felt so awesome to be held by him and have him cup my ass as he brought me close to him.  It wasn't the first time we kissed, but it was the best by far.  i pleasured him several times and after the last time, he "allowed" me to play with myself (in sissy fashion of course) and i came while i licked his balls one last time.  He also loved watching me lick up whatever cum spilled on to the kitchen floor!  i am beginning to really love his growing dominance.

Brian and Diane got together tonight, and i still haven't heard from Her yet.  She told me if i didn't hear from Her than Brian may be spending the night. 

i hate to admit it, but the fact that Diane has become submissive to another man seems to be a type of humiliation i crave.  In some ways, it seems to be a step towards making me a more complete cuckold.   But i also have a feeling there's even further to go. 

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Meeting a "Wife's" Needs

Other than going into the office just briefly yesterday, Diane decided to take the entire week off.  It's been nice.  We got to spend time together, talk, shop and just enjoy being together while our "boyfriends" are away on their own family vacations. 

Despite having my period this week, we've been rather sexually active.  Diane's teased me about how horny She's been all week and how much She misses manly sex with Brian.  i've pleasured Her as best i could (at least twice each day) orally and a few times, using a hand held vibrating dildo on Her as She fantasizes about Brian.  This form of pleasure for Her has given me an insight into some of their lovemaking.  Diane might be exaggerating some of the things She talks about while i pleasure Her this way, but there's clearly a change in Her approach to sex since She's been with Brian. 

She hasn't made love to me with Her own strap-on since i started my period on Sunday.  However, there have been multiple "sissy masturbation" sessions, even a few while i was still "fully pantied."  It does make for a little bit of a mess and Diane laughed and told me since i lacked so much control that "maybe you should wear a diaper instead of panties."  She's also been teasing me by saying that She hopes my period is a short one so that She can make real love to me before the weekend.  That's a good sign.  I'm expecting Her to let me know today that my "time-of-the-month" has come to an end.

We were shopping the other day and Diane picked out a cute little summer nightgown for me.  i also pointed out something that i thought would look good on Her.  Her first comment was "Do you think Jake would like it?"  i told Her i thought he would, but that i really liked it.  We bought it and She wore it for me the next night. 

As we were shopping i thought about how each of us works hard to please each other as their "wife."  In our relationship, we really are each others "wife."  i don't sexually pleasure Diane like a real man would, and we're both more than okay with that.  But She definitely pleases me like a wife gets pleased.  She's even back to calling me "wifey" more and more.  i am loving all of it.  The more She does these things, the more submissive and feminine i feel.

By all indications, She's loving it too. 

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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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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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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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"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!

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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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Flying "More Femme"

i leave with Diane today for about 5 days.  We're going to a niece's college graduation and will be flying out tomorrow.  The graduation is this weekend and we'll be spending some time with family. 

This morning, Diane told me that tomorrow i need to wear four items of feminine clothing for our flight out.   At first, i was shocked and incredulous about this demand.  Four items is quite a bit to wear without bring unnecessary attention to myself.  Diane told me i was making way too big a deal out of it and was worrying for nothing.  "I bet you could get by with more items than that and nobody would even bat an eye" She said.  

She proceeded to suggest several things i could wear in various combinations that would amount to four items.  Some of the things she mentioned were bra, panties, pantyhose, garter belt, thigh highs, ladies oxford or golf shirt, ladies slacks or jeans, ladies socks, a chemise, a girdle, etc.  There was more on the list but i can't remember.  She's correct (again), and i should be able to get the four items without much of a problem.

Wednesday night was an interesting one.  Brian did hook up with Diane, but couldn't stay very long.  When i spoke with Her later that evening, She said even though the time with Brian was short, it was still worth it.  "I still wish you were here tonight though.  I like being with Brian, but there's something special about having you there after he leaves" She said.  "Makes it feel more like I'm cuckolding you."  Those last words got me hard.

Also, i got up the courage to call Jake and am glad i did.  We're meeting for coffee next Thursday and i'm now sure this is going to work out.  We couldn't talk long but i finally asked him what made him approach me at the gym.  He in turn asked me if i was glad he did.  "Of course" i said, then realizing how i probably sounded a little too giddy about it.  "Well, I'm a little embarrassed to say this" he said "but I'd been looking you over for awhile and, well, was intrigued by your legs."

Wow was all I could think.  There was silence and i finally told him that now i was the one who was embarrassed, blushing too.  "Good" he said, "now I don't feel so bad."

i think this thing with Jake might work out after all.  Now i just have to decide what i am going to wear this afternoon!

See you next week :)

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