My Visit To Florida, Part I

I love being out of town because I can go shopping, be a sissy slut in public, and be much more daring than I would normally be near home. Once, I had the occasion to travel to Ft. Lauderdale to attend a surprise birthday party of a friend. I was traveling alone, and of course, I brought lots of sissy clothes and toys.

As soon as I got out of the airport in my rental car, I changed into a pair of suntan pantyhose and some denim short-shorts that crawl way up my sissy bottom. I wore platform sneakers that were still kinda fashionable at the time, a light top with an unpadded underwire bra. There was no mistaking that I was NOT a girl but a sissy boy.

I had several days before the party and had planned to drive to another city to visit an old friend there. So, I could priss along the way. Occasionally, when the situation allowed for it, I would get out of the car so I could be seen and giggled or laughed at. At a shopping mall, I parked and got out of the car and walk toward the entrance as a group of hot girls were walking out. They immediately noticed me but were politely quiet as they passed. Then came the snickers followed by the hysteric laughter. I love that humiliation. I can play the sounds in my mind over and over.

At one point at a gas station, there were no less than six women looking at me simultaneously from different angles. Some were filling up their cars; some were going in or out of the convenience mart. I had added a pair of lace anklets to the outfit to make it even more demonstratively sissy. The reactions filled the air from “oh my god” to giggles to outright laughter coming from several directions. I paid no attention as I was only the mindless priss looking for something in the back seat. But my face was burning red the whole time.

Several times along the way, I got into my thong leotard and tights and looked for opportunities to parade my sissy self to those amused by a pathetic sissy.

While there, I stopped in a local dance shop and had a most interesting experience. It was mid-afternoon on a weekday, and I was the only customer in the store. Normally when I visit a place like this I would call first and ask about trying things on, but since I was out of town and feeling frisky, I decided to just go in. Oh, I was dressed in something a bit more conservative than described above. I was greeted by the clerk. I browsed for awhile, obviously looking at the female leotards, and she said I was welcome to try things on if I needed to.

I found some thong leotards in my size and headed for the fitting room. While in there, I heard the bell on the front door, and it was obvious that a young woman had come in. She was very outgoing and talkative; in fact, she was a regular Chatty Kathy. I was enjoying listening to her while being in my fitting room trying on leotards. I was prissing in front of the mirror and starting to play with myself while I listened to her cute, bubbly voice.

I finally came out and had a chance to check out the customer. She was in her mid-20s, very outgoing, and started to chat me up as I did a little more browsing. I conspicuously placed two leotards on the counter. As the clerk made her way over to help me, the cutie was now curious about what I was buying and asked who I was buying for. I held them up and told her they were a couple leotards for me. She asked if I was a dancer, and I simply replied, "Um, actually, I'm a sissy... and I like to wear girl things." She was interested and amused by this, and she started talking about where she worked which happened to be a BDSM club across town. I couldn't believe my good fortune at hearing this. The clerk was also intrigued, and I asked her what they did there.

She said they got into mild bondage and discipline scenes there. She wasn't a dominatrix but a hostess. She was obviously way too bubbly and nice to be a domme. She said she welcomed people and served drinks and entertained a little. It was a commercial place that did mild scenes and must have just skirted the law. She said that all men were admitted free if they came in drag. I asked her if I could just show up in my sissy attire, namely my leotard, tights and heels. She said certainly, that would be fine. I also asked if I could get a good, sound spanking there. I was starting to get pretty daring in my conversation with this girl, who later told me her name was Kelly.

Kelly told me they did spankings, but they couldn't do it on the bare bottom. The clerk said she thought this was interesting and didn't know this kind of place existed. I told Kelly that I'd had a few private domination sessions in the past and had been humiliated with strapon dildos. She said they couldn't do that. I told her that I'd only been made to suck them. Now I was showing off in front of the clerk, who was being polite but was amazed at the conversation.

I said to the clerk, I'm sorry if this is freaking you out or anything. She said no, it was very interesting; she'd just never really heard of that kind of stuff before. I explained that I had never been to a club of any kind before but had only been to private sessions with a Dominatrix involving crossdressing, spanking, and humiliation with a strap-on. I really wanted to tell them about how I would lick my cum off the dildo, but I figured I was pushing it.

Kelly gave me some details about the club. It was a place where people could come in and do their own scenes. There are a couple Mistresses available to get into scenes. There were limits on what can be done. She gave me the location said they were open on Friday and Saturday nights. I would have time Friday, so I told her I was looking forward to a visit and a good, hard spanking!

To be continued...

The end of a relationship

Carla was a wonderful girl. She was a loving, giving person. Sexually, she was the most open-minded woman I've ever been with, but unfortunately she had baggage... Major baggage that I can't go into here, but let's just suffice it to say that it was bringing the relationship to a screeching halt. We really did love each other, but her low self-esteem (and I thought mine was bad!) was creating intolerable problems for us both.

In the bedroom, we likely would have progressed to her wearing a real strapon. I know she was up for that. And maybe we could have moved to her playing a little light domination. She was a little sensitive about being called a "whore" when passion was getting high and language was getting nasty, and believe me she could embarrass a sailor through gritted teeth as she ground and humped and fucked back. Calling her "my whore" was OK, but not otherwise. During one of our last escapades, I took a dildo and placed it between her legs and told her I wanted to be "her whore" and began to suck it. With a bit of a knowing smile, she put her hand on the back of my head and pushed me up and down on the cock for awhile. That particular scene didn't last long that night. I was hoping we could take it to having me lick cum off the dildo.

I'm pretty sure we could have gone there, but it ended soon afterwards.

Damn. All of the other components were in place. I was wearing lingerie in her presence full time. If I ever wore men's underwear, she would ask me if something was wrong. She had me eating cum. She was fucking my ass. Sucking cock should have been next. I was hoping I could have moved her along to dominating me with all the trimmings of humiliation.

That's really what I craved. I wanted so much to have her to stand over me in black stilettos wearing a 10" strapon, pointing to it, and telling me to suck it like the little sissy bitch that I am. I wanted her to make me wank off and make me lick my cum off her big cock while she called me a cum-eating cock sucking whore. I needed that so bad.

It just wasn't to be. We were on again, off again, off forever. Time to move on.

JamieLin, where are you??

JamieLin, I sure wish you'd put your blog back up. I was inspired by your writing. I wish you'd come back.

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.