A Cuckold's First Creampie

i apologize for the brevity of this post.  It's short for a couple of reasons.  The first one is that i haven't totally organized my thoughts about this whole topic yet.  i felt many different emotions about what i did and they seem like they're all over the map.  We're also leaving in a few hours for the weekend and i've still got to get a few things ready before i leave to pick up Diane at Her office.  i may post more this weekend.

Anyway, i did it.  i came home to Diane after She had been with Brian for a few hours on Wednesday evening and was immediately "put to the test" as She put it.  In a rather unceremonious fashion, i was quickly ordered to strip down to just my panties and get between Diane's thighs and orally worship Her.

Brian had been gone awhile and the most recent sex they had was by Diane's estimation, "a little more than an hour ago", but the scent and taste of their sex was overwhelming.

i hesitated at first but Diane, who was more understanding that Dominant, encouraged me to take my time and "savor it."  "You'll feel more like a cuckold when you're through."

She was right.  And i pleased Her in the process as well.
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Deeper Cuckolding

A week between posts is a long time for me.  The combination of family commitments, things to do and my own difficulty in mentally processing everything i'd like to write about are the primary causes for the delay.  i'm just going to give it my best shot.

It's been about seven months since Diane reunited with Brian at a wedding we attended.  So much has happened since then.  Most of what's happened I know about, but not what Diane revealed to me this weekend.

As She was going through some office correspondence on Saturday morning and making notes, She nonchalantly said "Well, it looks as if you won't be buying me condoms anymore."  It was a confusing statement and my initial thought was that She and Brian had somehow broken up and She wouldn't be seeing him again.   Then realizing that if that had happened, i would have more than likely noticed a change in Her moods, i began to think a little differently.

Awkwardly, i asked Her what She meant.  Again, it was something that came out sounding stupid.

"You know how careful I am" She said.  "I've had extensive blood work done for both of us.  Brian is clean as a whistle.  I knew I was free of anything, but in all fairness, wanted to provide him with the same level of comfort."

i didn't know what to say and could feel myself blushing, but not in a good way.  i felt nervous, uneasy, unsure and emotional.  i stayed quiet and continued doing what i was doing.   The silence in the room was deafening.

"Cat got your tongue?" Diane asked me.  "Don't you have anything to say?"

Again i hesitated and said "i'm not sure what to say.  i want you to be happy and i'm sure you've thought this through."

"Of course I have" She told me, "But, I want you to be happy also.  I think you'll enjoy it as well, don't you?"

All of these questions that point out my submissiveness and sissy cuckold status are difficult to answer.  i know the answers but the words are difficult to say.  Speaking them in some ways is an admission of sorts, an admission of many things.

"i don't know.  If it makes You happy, i'll enjoy that" i told Her.

"Well, we're going to find out this week when Brian comes over for a few hours.  When I call you to come home, there will be a little something waiting for you between my legs" She said.

Brian comes over tonight.  i'm going to find ways to keep myself busy while waiting for Diane to call.  i wish i could be with Jake but that's not a possibility.  i'm very anxious about the whole thing and i'm probably making a mountain out of a molehill.  After all, i'm going to be doing what a countless number of other cuckolds do, and i bet many of them enjoy it. 

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Sex for Sissies

Last week i received the following message on my Tumblr Blog, A married sissy, from an anonymous follower:

"Hi, I read your blog regularly and really enjoy it I was wondering whether you think you might ever have 'normal straight sex' again? and If you miss it?"
Since i couldn't respond to the anonymous questioner privately, i suppose he or she expected a public answer on my tumblr. blog.  i've thought about it for several days because it's a very intimate and personal question and decided just this morning to answer it her, with a link to this post on the other blog as well.

i made the decision to post the answer this morning because coincidentally, Jake asked me a very similar question when we met for coffee this morning.  We got to talking about some pretty personal things, among them our sex lives with our wives when he asked how often i had sex with Diane, sex meaning regular male-female intercourse.  i feel bad because i lied to him.  i told him we had sex about once per week, sometimes more, sometimes less.  i also volunteered that i performed oral sex on her more often, since it was something she enjoyed, and that my estimate of regular sex once per week was probably a little on the high side.

Jake doesn't know that i'm a cuckold and that Diane gets her enjoyment of "normal straight sex" from her boyfriend Brian.  He also doesn't know that it's been a very long time since i've had this type of sex with Diane.

Before i answer the question, i want to tell you about something that happened about a month ago when i was pleasuring Diane.  She had just had a very powerful orgasm, one that was more intense than usual.  While between her thighs, i became very, very aroused at how excited she seemed; more aroused than usual.  As her orgasm began to subside, i had a strong urge to make love to her like a man does.  My penis was hard, stiff and felt larger than usual.  i wasn't about to force myself on her by any means but felt like gently inserting myself into her very, very well-lubricated vagina.  i got up from between her thighs, knelt between her legs and held my penis against her vaginal opening and looked at her with a smile.  Diane had other ideas....

"Hey! Hey! Hey!" she said with a grin of her own as she gently pushed me away, "What do you think you're doing?"

i really wanted her, if for no other reason than to feel the warmth of her vagina envelop my penis, knowing that her lover was there on a regular basis.  i stammered a bit and said "i just thought i could make love to you just a little."  It sounded so stupid after i said it.

"You know better than that" she said.  "Now be a good sissy and lick me again."

It made me even hornier.  i did lick her again, this time the orgasm taking a little longer but in the end, she seemed to enjoy it just as much.  As i licked her, i thought about how she had just dismissed me.  When her orgasm began, the humiliating manner in which she had  rebuked my efforts and told me to return to my licking duties was too much for me.  i came at the same time she did and messed the sheets of the bed.

Just a few moments later, after i submissively apologized for messing the sheets, she said "I don't know what's gotten into you.  All this aggression and lack of discipline.  Maybe you do need a chastity belt."  i don't think i'll end up in chastity because Diane thinks they're too much work and She hasn't expressed an interest in them.

As a sissy, i do get a fair amount of sex.  But the sex is always on Diane's terms, or when i'm with Jake, his terms. i provide them with sex and in turn, they also provide me with pleasure when they see fit.  i'm allowed to masturbate in front of them and with Diane, She sometimes enjoys stroking me softly until i cum.  i've also had orgasms while Diane takes me with Her strap-on, and those are very enjoyable.  That's the extent of sex for sissies, and it's probably as it should be.

Will i ever have "normal straight sex" again?  i don't think i will.  It might happen, but i think it's unlikely.

Do i miss it?  Yes, i do miss it.  However, i don't miss it nearly as much as i once did.  My needs to have "normal straight sex" seem to diminish the more i get into the married sissy lifestyle.

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Wifey Stuff

My part-time consulting commitment has been rather slow lately.  It should have given me more time to blog but it hasn't worked out that way.  A couple of other things came up this past week which kept me away from the computer.  And, my consulting thing is going to heat up in a couple of weeks when the next phase of the project starts.

In the meantime, Diane's kept me focused on more "wifey things" as She likes to call them.  The list of to-do's seems to get longer every day.  Our house looks spotless, with not one thing out of place.  Washing floors, walls, windows, and anything else you can think of that can be washed keeps it looking that way.  There's also plenty of reorganizing, filing, cleaning out the garage, etc.  It never seems to end. 

Since i'm dressed all the time when at home, all of the housework is done en-femme, which definitely puts me in the housewife mood, but doesn't take away from much of the drudgery.  i change into more suitable attire when i go out to run errands, only to get back into my women's clothing when i return home.

i made a couple trips to the dry cleaners this week to bring some clothes Diane took out of our large cedar closet that She plans on wearing this fall.  She would take them out and lay them on the bed before She left for work, telling me they were to be taken to the dry cleaners.  Yesterday, amid the half dozen or so items She left, was one of my maids uniforms that i hadn't worn in a while. 

"It could use a cleaning" She said.

It's a satiny black uniform, with a flared skirt edged with lacy ruffles.  There are also ruffles at the arms and neckline and a sewn in white ruffly bib front.  It clearly has the look of a costume more than a working maids outfit.  Someone seeing it would definitely know it wasn't meant for everyday maids work.

It was embarrassing to bring it to the dry cleaners.  The young girl (probably a high school aged teen working a summer job) smiled and said "Oh this is so cute" when she took it.  i had a nervous giggle and couldn't help blushing a little.  i wondered what she thought.  If she only knew what i was  wearing underneath my shorts and shirt!

Yesterday was also the start of my "period", two days earlier than i had planned.  The tampon and pad i were also set out by Diane yesterday morning.  Those two items are far more telling of my lifestyle and status than the  maids uniform i brought to the dry cleaners. 
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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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Babydoll Boy

It's been a busy week, but not busy enough where i couldn't at least post a couple of times.  However, it's been a pretty emotional week for me.  And maybe for Diane as well.  Predictably, to some readers and some who have left comments, i'm beginning to struggle with Diane's decision to cuckold me with Brian.  We knew it wouldn't be easy and some struggles were to be expected, but i'm having a much more difficult time than She is.

And therein lies one of the problems i guess.  She's enjoying Herself tremendously.  But that's only one of the issues i've had to deal with this week.  The other involves Diane's close friend Linda.  Linda's also having an affair with a married man, so i suppose it would be natural that the two of them would share things.  However, i never thought that Diane would share that i know about Her and Brian.  i almost died when She told me that. 

Part of what led to Diane doing so had to do with how turned on i get when Diane would verbally tease me about telling Linda about me being a sissy cuckold.  Linda's very attractive and Diane knows that i think she's very sexy, so She's often brought up Her name in our fantasy play scenes.  Many involve me serving the two of them as a sissy maid or even being disciplined in front of Linda.  So apparently during one of their more intimate discussions, when Linda asked how Diane made it look so easy to meet up with Brian, She explained to Linda how i knew about it and was ok with it. 

Diane insists the conversation was in the strictest confidence, and that Linda doesn't know that Diane told me about it.  So when Linda's around, i'm supposed to act like she knows nothing about my being a willing cuckold. 

i'm also jealous that Diane seems to have none of the emotional issues that i'm dealing with.  i'm jealous and envious of the calm and collected way She's dealing with all of this.  i made a comment that got Her upset.  i told Her that i felt She was exploiting my submission.  She doesn't see it that way at all.  She feels She's helping me with it, nurturing it, and providing an open environment where i can experience what i truly want. 

It's an emotional roller coaster.  Everything that's happened are things that i've fantasized about before and got turned on when i did.  Yet when they happen and i have to live through them,  get all emotional about it.  When it's all over though, admittedly there's a certain fulfillment that i do enjoy.

i do have a date with Jake tomorrow.  i'm hosting him here at home where i'll have the house to myself all day.  Diane won't be home until 7 PM.  I'm also going shopping today for something to wear for Jake.  He wants to see me in a baby blue short nighty.  Pretty specific.  i love the dominance that specificity shows. 

i told Diane i was going shopping and got permission to buy the babydoll.  She thought it was pretty cool that i was going shopping to please my boyfriend.  She's already sent me a text asking:

"Has my babydoll boy done her shopping yet? xox D"

She knows how to push my sissy buttons.  That's one of the reasons i still love Her.
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A Cuckold Night

Tonight's a cuckold night.  I'm home alone and Diane is spending the night with Brian and a rather upscale hotel downtown.  She's been primping for it all week; purchasing new lingerie, getting a pedicure and manicure at the spa, and overall just being obsessed with seeing Brian tonight.

i traveled a bit this week on business and this part-time job is becoming a grind for both me and Diane.  She wants me to quit and has given me an ultimatum.  Either my hours reduce dramatically or i'll be forced to resign.  "Your housewife duties are suffering and I'm not going to put up with it" She said.  i understand our contract and She's right.  "Don't you miss being a full time housewife?" She said laughingly.

Her teasing might be the same but it seems a little more pointed lately.  Maybe i'm just being overly sensitive.  She's also becoming more dominant and in some ways, i feel She's being a little less "careful" about Her affair with Brian.  Meeting him at the hotel tonight is an example of what I mean.

Before She left this morning She reminded me that i was due to start my period today.  The box of tampons and a pad were left on the vanity for me to use.  Maybe that's why i'm feeling overly sensitive.

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