Carla Takes Me

This is the closest Carla came to dominating me. She knew I loved to be stimulated anally. Being a lover of anal sex herself, she knew well the delightful feeling of being penetrated “back there.” There were many times while blowing me when she would finger fuck me into a crazed orgasm. I often brought over a number of favorite toys for our weekends together which included a medium sized butt plug. She knew well the affect it had on me. By this time, I had not yet purchased a strapon, but I had talked about them, and I think Carla would have been open to using one on me. We broke up before we ever got to trying that.

However, one night Carla lubed up the butt plug and I smiled and rolled over to have her put it in my bottom. Usually, it was put in and stayed in while we played and fucked. But this night she gave me a lot more than I expected. I could sense Carla was positioning herself behind me, and I turned back to see her holding the plug against her pubis and getting ready to mount me! She had a wicked grin on her face. I let out a stunned, “oh my god!” as the cold KY slathered up and down my crack. Then gently, she pushed the plug in about halfway, pulled it out most of the way, and then buried it as she lay on top of me.

I whimpered a breathy “oh!” as I felt like an innocent girl being taken for the first time. Carla slowly pulled the plug back out and thrust it back in again. After about a half dozen strokes, I thought we might move on to some other mutually satisfying activities. With a smile, I started to turn around and roll over. Carla had a determined look on her face, and not so gently pushed my shoulder back around and pushed my face into the pillow. She pumped faster as I moaned out loud into the bedding.

She got my ass up higher so she could get a better stroke. She was very lean and strong. I was amazed by her persistence in doing this all while holding the base of the plug firmly against her pubes while she fucked me like a man would. Several times she grabbed me with both hand by the hips and just slammed against me, slapping her pelvis against the plug, driving against it every time. I was whimpering and nearly crying by this time, but she was relentless as if it was her cock, and I wasn’t going to deny her getting off.

Several times she would tease me with a reach-around, and stroked me with one hand as she butt fucked me with the other. There was some lingerie on the bed, and she took a pair of panties and stroked me with them. Knowing I was getting close to the edge, she pushed me back down with a half-slip and several pair of panties between my dick and the bed. She fucked me and giggled as I humped the lingerie. As I moved, I was also fucking myself against her.

Between the silky lingerie rubbing my cock and the mixture of pain and pleasure in my ass, I was in a frenzy. Carla whispered for me to let go. I felt like a virgin bride at the hands of her husband on her wedding night being urged to let go as he fucked her. I came like a bitch, I squealed, I screamed, I whimpered, and Carla kept right on fucking me. I thought she wasn’t going to stop, and I was about to beg her to because it was starting to hurt. Finally, she collapsed on top of me while I laid there with a plug in my pussy-bottom and a huge wet spot in the lingerie under me.

After some time, Carla started to kiss the back of my neck and tell me how good I was. I felt like I was just taken like a girl. After we rolled over, she put the covers over me, and she held me in her arms. I felt safe and protected.

House Dressing

One evening on the way over to Carla’s apartment, I picked up a couple of salads from Wendy’s. There was a promising night ahead. When I got there, I was already turned on, and as she got our dinner out of the bags, Carla wanted a panty report. That is, she wanted to see what panties I had worn for her that night. I was only too happy to oblige, and quickly got my pants off so I could model my panties for her. Of course, she approved with a few gropes here and there, which only served to get me all the more turned on. She even got me out for a few strokes to tease me for what was ahead after dinner.

She had put the salads into some bowls of her own, and we were going to dine on her couch. Feeling frisky, I was stroking myself and jokingly asked if she would like the “house dressing.” She replied, “Well, of course!” and her wicked smile. I acted like I was going to jerk off into her salad, but of course I was only acting. She continued to hold out her bowl.

I started to sit down. “I’m waiting for the ‘house dressing,’” she said coyly.

“Are you serious?” I asked.

“Well, you offered the house dressing, and I accepted. Now, when do I get the house dressing, waiter?”

Shit, she was fucking serious! I stood back up while she held out her bowl. She had a grin with raised eyebrows. She started a little role-play like I was the waiter in a restaurant.

“You know, I’ve heard the ‘house’ is really good… very creamy and warm… just the way I like it. I hope you’ll give me a little extra on my salad.” She started to play with my balls. “Can I pump it for awhile?”

“Yes, of fuck!” My panties were down to my thighs as Carla pumped my cock with an innocent look on her face. She continued to make her little teasing double entendre remarks in a matter-of-fact tone of voice. I took over and started to jack it faster.

“Is that dressing ready for my salad yet? I’m getting hungry!” She acted like she was getting impatient.

I started to moan and scream. She held the bowl in place to be sure she caught it just right. As I started to shoot, she rotated the bowl to get coverage of the salad with the house dressing. I couldn’t believe I was cumming on her salad.

“That looks yummy!” she said with wide eyes as she licked her lips. Another spasm of cum shot out on top of the lettuce leaves. She continued to rotate the bowl to try to catch the jizz dressing on more of the lettuce. I moaned again as she giggled. Unbelievable!

I collapsed on the couch next to her as she laughed and thanked her waiter for delivering a nice amount of the ‘house.’ She promised a nice tip for me later. Next was a mind fuck the likes of which I’ve never experienced before or since.

Slowly, Carla took her fork and selected a few leaves of cum-soaked lettuce and ate it. I was stunned that she’d actually do it. I mean, first of all, it was now cold. And secondly, it wasn’t like it was on me or something. She was just eating salad with jizz on it.

“Mmmmm…. this is very good dressing,” she reported. She took another forkful as I watched in stunned amazement. Then, by about the fourth forkful, she carefully dipped leaves into the puddles of cum still in the bowl and then held it up to my mouth to feed me. Inside, I thought ‘I can’t possibly do this,’ but Carla had this way of just doing things with full expectation that I would participate, and I would. I ate the cold salad with the cold cum dressing. Truthfully, it wasn’t really as bad as I thought it would be since the lettuce was nice and fresh. The water content diluted the taste of the cum.

She then prepared another fork-full for herself and ate it. Again it was my turn, and I obliged as she fed me. We giggled like two girls wearing our panties eating on her couch. But this was just another lesson in sissy cum eating. Carla had no shame when it came to sex, and from that shamelessness, she was teaching me to enjoy eating cum the way she loved it.

There were many shared cum eating episodes to follow. Almost every blowjob was snowballed. She might give me a handjob in the car and then lick her fingers and offer some of it to me so I could help her lick her fingers clean. She liked me giving her a "facial" so that afterward I could lick it off her face and we could share it in our kisses. In the end, Carla taught me to be a cumslut.

Carla's First Lesson

Wearing panties every time we were together was by now typical and soon progressed to my wearing pantyhose, which she just LOVED. I wondered just how far I could go with this. Could I get it to the point I was with Terri of years gone by? Could we play dress up together and wear bras and everything? Short answer: mostly yes, all in due time. More about that later.

As I mentioned in my previous post, Carla's lessons were in the form of learning acceptance. One of those lessons came in a most unexpected way. First a little background. This girl could suck cock 'til the cows came home. She was never slutty. She never acted slutty or talked dirty. It's hard to explain, but she was the only woman I've ever known who could look demure with a dick in her mouth. And, OMG, she could deep throat! I've never experienced that before or since. At first it was scary! I thought she was going to swallow my cock and consume it. She always swallowed my cum and was certain to get every last drop by stoking it in her mouth until my balls were drained and I went limp from the pain.

But this lesson is really about cum. Cum. Cum everything. Cum all over your face. Cum in your mouth. Cum down your throat. Hers... and mine. You see, while some guys are totally turned off by a woman kissing them after given them a blowjob, I've always thought it was particularly sexy to french kiss a woman after she had swallowed my load and I could taste the remnants of it. I wanted Carla to know how evolved I was by letting her know that I thought the taste of cum was sexy. I even licked it off her breast after cumming on her chest one time.

SNOWBALL

Once after giving me a particularly ball-draining blowjob one night, Carla gave me a VERY big surprise. She had sucked me completely dry to the point where I thought I might not ever cum again! I was lying there in an exhausted heap, and she returned quietly to my side and snuggled me for a moment while I caught my breath. Several minutes had passed before I started to show interest in her again and started kissing her. She slowly moved to gently kiss my lips, then moved above me. Eventually as her tongue met mine, an avalanche of warm cum began draining into my mouth as she continued a most passionate kiss. It was intoxicating. Her mouth was now sealed over mine to prevent any loss of the jizz as she stirred it in my mouth with her tongue.

There was no choice here: she was on top, and this load was mine to swallow. She had patiently saved it and brought it back to me as a gift. This kiss lasted for at least ten minutes while she silently demonstrated to me what an erotic woman does with a mouthful of her man's orgasm. It wasn't until all of it was extracted from her mouth and she was sure I had swallowed every last drop that she removed her mouth from mine and returned to my side without a word. I was speechless.

I had eaten my cum before, but this was the first time I had really experienced it, really savored it in my mouth. She had just shared with me a very intimate experience that is one normally only a woman could have. Carla gave me that experience--without any shame or guilt--as a gift.

Carla

Carla was the all-time kinkiest woman I've ever dated. She seemed to have no shame at all. We became emotionally and sexually involved on our first date. I spent the night on Friday, and we fucked our way well into Saturday. After showering, I was going to run home, get some fresh clothes and return. I thought I'd test her a little by pointing out that I didn't have any clean underwear.





This is a little game I've played with girlfriends to see if they'd offer something of theirs. It had never worked in the past.















"Well, just don't wear


any," she said with a wicked smile.

"That always feels so yucky," I whined. I'd hoped she'd come up with a helpful suggestion. She did.














She smiled coyly. "Would you like to borrow some of mine?"

I blushed and stammered. I'm such a good actor. I let her talk me into it. As she pulled opened her panty drawer, I gasped at all the sexy and silky panties she had. "You have some naughty little things here..."

She pulled out one of the more daring pairs and held them up. I protested in feigned embarrassment that I couldn't wear something like that. But I had to be careful; I didn't want her to pull out some boring cotton ones.

"Well," I said with a smile, "since you're lending me your panties, I should let you choose the ones you'd like me to wear."

Carla was like a kid in a candy store considering so many different styles to find the right one that she was going to have my wear home. As she would hold up the smaller bikinis, I would remind her that I needed some room to accommodate my equipment.

After considering at least a dozen pairs and being taken on a very nice tour of her lingerie drawer, she finally displayed a pair of silky white bikini panties with a sheer lace front inset. She held them open near the floor so I could step into them, and my dick started throbbing. As she started to bring the panties up my legs, Carla took notice of my condition which was now right in her face. She smiled approvingly, and said, "Well, are we getting a little turned on here?"

She was teasing the shit of me and loving it. Once she had pulled the panties up to the top of my thighs, she acted as if she didn't know how she would get them over my dick sticking straight out. She looked quizzically at the situation and said in a dumb voice, "Hmmm.... well maybe they won't fit after all."

"You might have to make things fit!" I suggested.

"O-o-o-o-hhhhh," she said, and then giggled.

Then she softly handled my dick in such a way as to be stroking it as she made various attempts and re-attempts to put it in the panties. The moving and stroking caused me noticeable frustration which I voiced.

"Well I'm sorry," she said in a mock apologetic tone, "I'm just trying to get everything to fit right."

"You're only making matters worse!" I countered.

"Yes, I can see that," she gleamed.

After all this fussing, she finally had me turn around so she could admire the fit. She was enjoying the view. "I love it!"

I thought I was in heaven. Here was this incredibly sexy woman who had just put me in her panties, and she was enjoying this! Could I tell her that I have my own collection at home?

I drove home with a raging hardon wearing these lacy underthings, debating all the while if I should wear them on my return. I decided I should act "normal" and return wearing men's underwear and politely thank her for the loan but also let her know that I really did have fun wearing them.

On my return, she was actually disappointed that I wasn't wearing her panties. I told her I'd be glad to wear them again. Before the weekend was over, we did have another experimentation session with some other pairs of Carla's panties. I knew this was going to be a fun ride.

I brought up the subject of panties a couple times again when we talked on the phone. This was still almost too much for me to believe. She really liked seeing me in panties! It was the subject of some coy conversation, and I hinted at the idea of wearing something "for her" upon my return.



When I returned, I was in fact wearing a pair of my own lace trimmed panties. I was really nervous about it. This would be a revealing moment as she would know that I had my own. Then again, I figured if things went terribly wrong, I could also make a joke of it and tell her that I bought a single pair as a joke just to play with her head.

After I had been there for awhile, I told her I had a surprise for her and hinted where the surprise might be. Once she took the clue, she put her hand down my pants, she smiled and said, "Well, we know what they are, but we need to find out what color they are."

Before long, she was giving me more of her panties on permanent loan and buying me frilly, lacy, bikini panties with the expectation that I would wear them for her on dates and, more importantly, in bed. She knew how much they turned me on, and she reaped the benefits thereof.

Carla seemed to have no inhibitions whatsoever about most anything concerning sex. It was only my inhibitions and fears that kept me from fully revealing myself to her.

Now you're probably thinking this was too good to be true. It only lasted less than a year for reasons that I will soon reveal to you, but in that year, Carla taught me a lot about self-acceptance.

Leotards and Tights

One of my favorite sissy outfits at home has always been leotards and tights. I would dress up in my favorite outfits consisting of shiny black tights, a bright colored thong leotard over a padded bra, and high heels. It was a very sissy-slut look!

I started a late night ritual of going out wearing my dancewear under regular shirt, pants and shoes. In the car, I'd take off my pants, unbutton my shirt and put on my slutty pumps. Then I'd have fun just driving around in my ultra-slut outfit. When I was sure I wasn't going to be noticed, I would take off my shirt and drive in just the leotard and tights with my ample, shapely breasts jutting out on either side of the seat belt. With my dick tucked tightly inside my tights and leotard, I would rub my crotch for hours as I drove around feeling like a naughty dancer girl. Sometimes I would have a butt plug inserted, making the ride all the more erotic.

My self-daring brought me to drive past night clubs where I knew really hot and often drunk girls would be coming or going. I would time things so that I would be out of my car, totally exposed in my sissiness in front of a group of hysterically laughing women. Feigning embarrassment as they saw me, I would try to cover my boobs, turn and walk the other way. This only served to entertain them all the more as they caught sight of my thong bottom in shiny black nylon. Embarrassed and humiliated, I would run off awkwardly, teetering in my 3" heels. One girl ran after me so she could pinch my nylon covered bottom. Another wanted to squeeze my padded boobs. It was a classic case of reverse sexual harrassment.

This little scenario was met with dozens of appreciative audiences of women of various ages. Sometimes these women would start up conversations with me. Frequently they would compliment me on my legs and ass, and sometimes they'd ask me why I was so attired. I would usually tell them that I lost a bet and my girlfriend was making me do it, or I would simply tell them the truth that I'm a sissy. On a few occasions, the girls would feel me up for laughs. The giggling and laughing was positively addictive.

One girl put her hands on her hips, and with a look of contempt asked, "Are you looking for a man to fuck you?" Some of the things are still burning in my ears.

My craving for this humiliation caused me to become more daring. Sometimes I'd go for the jazzercize look and instead of wearing the bra and heels, I'd just wear sneakers. I made an unlikely looking male candidate for an aerobics class. Only a sissy would wear a leotard and tights!

I had a lot of fun trying on leotards in dance shops, too. Most places were friendly to male clientele, and I was permitted to try on all varieties of feminine dancewear in the stores. Some of the clerks couldn't believe I really wanted to try on thong leotards.

Women's Jeans in Public

I just had this thing for Chic jeans. They were the hot pair at the time, and I ALWAYS noticed whenever a woman wore them. The logo stiched in the back, the inverted curve in the pockets that came to a point. There was also this little reinforced stitch at the bottom of the fly that was unique to the brand. I could tell from any angle that a woman was wearing them. Terri wore them and looked hot in them, and I had always wanted a pair.







After we split up, I bought a pair and strutted around my apartment in them, checking out my ass in the mirror. I had a way of pulling up my pantyhose that gave me this sexy, feminine ass that looked really hot in Chic jeans. It was a long time before I finally worked up the nerve to wear them in public.







I was empowered one day when I saw this guy in a public building near where I worked. He was with his girlfriend, and he was wearing Chic jeans! I was stunned. I followed them for awhile. Did he know he was wearing girls' jeans? Was he wearing her jeans or were his own? I had to do this, too!

When I finally did, I wore them with a jacket or sweater over the logo. When I would let the logo show, I was making the message clear: "I'm wearing girls jeans!" I had a bit of control that way. Even though the pocket came to a point, from a distance, nothing really looked out of the ordinary. Then, if I wanted to dare expose the fact that I was wearing feminine jeans, I could let the jacket ride up and they could easily see that yellow stitched logo that sometimes literally had young women in stitches.

At first I wore them with my regular shoes because that's all I had other than high heels. I'd go to the mall and pick out a couple really hot girls, get myself in front of them, and let the jacket ride up. Sometimes there would be no reaction, but sometimes I could hear the giggling and the outright laughing when they would realize what I was wearing. The comments like, "Check this out," or "Oh my God! That guy's wearing Chic jeans!" would make it even more of a thrill.

Once, two girls followed me around a mall for about twenty mintues while they snickered and whispered to each other. My face was burning in humiliation.

I still have about five pair of Chic jeans. They're so comfortable. There was a point where I started wearing them pretty regularly.








But sometimes for the time spent, the reactions were just few and far between.



Now, if a guy is wearing back-zip jeans, there is absolutely no mistake.

I'd wear pants like these out in public and if a group of girls saw me, there was almost always a guaranteed reaction. Tight in the front with dicklet tucked away, no pockets, zipper in the back. They'd get hysterical!! (I didn't have a chain like in this picture)

Sometimes young girls in groups could be almost vicious dealing with a little sissy boy. Some of the remarks were priceless. "Look at this fag!" "He's got a girl's ass!" "Ohmigod, is that like an open invitation?!!"

Shopping excursions in my sissy jeans were were almost always humiliating.

Deeper Needs

Terri was always understanding and supportive of my desires to wear lingerie. Every morning as we dressed for work, we’d put on our pantyhose together. We’d wear each other’s things. There was one shared panty drawer. She was fine with me wearing lingerie while we had sex. We engaged in many fantasies involving me putting on women’s underwear.

An example was her as the clerk in a lingerie store helping me try on bras and panties in the fitting room. At first, she's a bit put off by having a man trying on the delicates, but she's trying to be professional. The fit of the panties wasn’t quite right, and she dutifully fellated me to get my erection to go down. All in the interest of a proper fit, you understand.

Still my need for humiliation involved fantasies such as getting caught trying on panties and being punished for the act by being forced to put on a bra and pantyhose and heels; then being butt-plugged and made to suck a dildo while being verbally degraded. It’s that whole shame thing. Terri was a good actress, but she was never going to be a dominatrix, even a soft one.

At the same time, her needs weren’t being met by a sissy who was a lousy fuck. Most of us are, after all. Let’s face it: while real men are focusing on the feel of pussy and making a woman feel good, we’re busy fantasizing about bras and panties and hose (oh my!). We can’t get it up if we’re not fantasizing or engaging in sissy behavior. That’s the plight of sissies.

So over time, she started to look elsewhere for real sex, and as I look back, I can’t blame her. She would be out late with some lame excuse while I was home dressing up and jacking off.

We had discussed the possibility of a three-way, and she was open to the possibility. I had confessed to her that I wanted to suck cock, and that didn’t bother her. I hadn’t told her that I had done it once before we met. What a wonderful memory that was.

In a crazy moment five years earlier, I picked up two women in a bar. I knew one of them was a very passable transvestite. I was pretty drunk. I invited them to my apartment, and we started having some fun. The TV was just beautiful with long, slender, pantyhose covered legs.

I showed them that I was wearing pantyhose and a bra. The TV and I started feeling each other up. The woman sat on the bed while I knelt in front of the TV. I felt up her legs and pantyhose and started to rub her crotch.

The woman said, "I think he wants what you have up there." She pulled down her pantyhose and panties and revealed a beautiful 8" cock. Now this was a dick any woman would enjoy pleasuring. I was delighted to hold it and stroke it, and in short order, I put it in my mouth. It was wonderful feeling it slide in and out of my mouth while hearing his feminine voice moan. Before long, I was sucking cock like a whore, my head bobbing up and down while I kept a good grip on the shaft stroking it. I was making shameless slurping noises. What a sissy cocksucker!! He didn't cum, but I wanted him to. I felt wonderfully feminine and submissive doing this as the woman looked on. She didn't really humiliate me, but she was encouraging and saying things like, "That's right, suck that big cock!"

I never sucked another real one, but ever since then I've enjoyed the sensation of my lips wrapped around a dildo and my tongue licking its head especially at the command of a dominant woman. Of course, it's also a lot safer than the real thing. There's just something absolutely overpowering about a woman holding a huge dildo between her legs ordering me to suck her cock for her amusement.

I can understand how women can sometimes achieve orgasm from giving head. At times I’ve worked myself into such a frenzy that I’ve gotten lost into a pseudo-orgasm of my own. Eating cum is particularly emasculating. It’s something I often find difficult to do on my own unless a woman is ordering to do it. Girls laughing at me while I'm licking it up makes it especially humiliating and erotic.

Oh... I’ve digressed, haven’t I? Like I said, Terri never knew about my cocksucking experience, and we never had that three-way. I couldn’t handle the fact that she was sleeping with another guy.

Today, I have cuckold fantasies. I wonder now what it would have been like if I could have stayed on as her sissy maid. Maybe she could have talked her lover into letting me suck his cock while she looked on. Then they could have ordered me into the corner to sit quietly while he fucked her good, they way she really needed it. He could show me how it's done. Then while I’d sit there in jaw-dropped awe while she screamed in ecstasy, at least I’d have the pleasure of knowing that the dick that was giving her such a noisy orgasm, I got hard for her with my own sissy mouth.

So Terri and I split up. It was mostly amicable, although we argued over some clothes. “No, those were my panties!”

Only a sissy boy would argue over a pair of panties.