Shemale Experience

Shemale Experience

Top Posts My First Shemale Encounter Categories

Cocks (1)

Cum (2)

Fantasy (3)

Hookups (3)

MILF (2)

Shemales (1)

True Stories (2)

More Perverts

Girl on the Net

Already have a WordPress.com account? Log in now.

Debauched

Customize

Follow

Following

Sign up
Log in
Copy shortlink
Report this content

View post in Reader

Manage subscriptions

Collapse this bar

Privacy & Cookies: This site uses cookies. By continuing to use this website, you agree to their use.
To find out more, including how to control cookies, see here:

Cookie Policy

I consider myself to be straight, but with an active shemale fetish. Go figure.
It has everything to do with cocks. I’ve always been visually stimulated by them (specifically big, thick, veiny dicks) as well as glorious, messy cumshots. However, the rest of a man’s body does little to turn me on.
Cocks started to appear in my fantasies from time to time during my teen years. I was initially surprised but didn’t suppress the thoughts. I imagined stroking them, sucking them and even swallowing cum. In college I experimented with a guy I met through IRC (more on this story later) but I just couldn’t get into man-on-man action at the time. It’s something I’m still willing to try out.
My desire for dick – and just dick – continued well into my early 20s. In order to satiate these urges, it became apparent that I should either find myself some anonymous gloryhole action or track down a shemale.
Theory: I think lots of straight guys can get hard looking at dicks but they’d never own up to it. This is where the shemale fetish comes in – femininity, tits and a juicy piece of meat between the legs is a win-win situation.
I was 24 when I first communicated with a shemale online. Let’s call her Cindy.
We found each other through the AOL Member Directory search and started casually chatting. I can’t remember who first initiated. Cindy was quick to volunteer her stats. Six feet tall. African American and Caribbean mix. 42DD. Ten inches long and six inches in girth. (!!!) Before long we were exchanging photos. I showed her my cock and ass and she returned the favor with a face pic.
Each time we chatted Cindy invited me over to her apartment. A couple of times I agreed and then cancelled at the last minute like a jackass. I really wanted to explore the fantasy always chickened out. A year passed and we periodically stayed in touch.
I vividly remember the night I finally met up with Cindy. It was bitterly cold. December. My then-girlfriend and I just had an epic, hurtful fight. I logged on and immediately messaged Cindy my phone number to let her know I was for real this time. She texted me her address and I was on my way.
I pulled into the parking lot and sat there for a few minutes shivering from nerves and the bone-chilling cold. Eventually I mustered up the necessary courage and approached her door. Cindy answered in a robe and panties, towering over me but looking completely feminine and smelling like a woman.
Cindy led me into her apartment and got down to business. She sat me down at the end of her bed and approached slowly, opening her robe and burying my face between her warm chocolaty tits. They were massive and firm. Definitely man-made. She took a few hits from a joint, undressed me and told me to get myself hard for her. I laid back and locked eyes with Cindy through the sweet-smelling haze. She licked her shimmering, luscious lips while I stroked. It was very clear who was in charge.
She ordered me to get on my knees in front of her and guided my hand between her thighs, where I could feel something pulsing and growing. It was tucked back but swelling and straining against the fabric of her panties. Cindy pulled the strings down over her hips and IT popped out, bobbing in front of my face. I was in shock. This was truly a monster cock. 100% as advertised.
I wrapped my mouth around the head of Cindy’s dick as best I could and began to give her a novice blowjob. I know she’d received better ones, but hey, I was learning. It was difficult to produce enough saliva to keep her cock wet and slippery. The thing was just so damn big . I worked both of my hands up and down the shaft with my lips and tongue around the head. The salty taste, coarse texture and the smell of pot and girl in the air had me completely intoxicated. I was finally fulfilling my fantasy!
As I sucked Cindy, her large hands roughly seized my ass cheeks and I could feel a well-manicured fingertip probing my hole. In previous chats she detailed all the various ways in which she wanted to violate my ass. It was something to consider, but I wasn’t quite ready for that yet.
I finally came up for air and she pulled me onto her bed so I was straddling her hips. While watching me stroke, she shot a load onto her stomach and then instructed me to cum. I obeyed and squirted hot jizz all over her horse cock. Cindy continued pumping for a bit, slicking up her meat with my load. It was so fucking hot.
While we were cleaning up she told me she was a Chicago native and for some reason I asked if she was a Cubs or Sox fan. Cindy didn’t have a preference. We both finished wiping ourselves down and bid each other farewell. She slapped my ass on the way out the door and announced that she’s “having that” next time we meet. I saw Cindy two more times after this initial encounter. But those are stories for future posts.
To wrap up: My shemale fetish remains active to this day and I indulge in it from time to time.
Any other guys out there with shemale urges? What specific things do you look for when encountering (or fantasizing about) a shemale? Be sure to leave comments below!

I love writing about real-life sex stories, debauched fantasies and random thoughts on dating and sexuality.
View all posts by Voyager

Fill in your details below or click an icon to log in:

You are commenting using your WordPress.com account.
( Log Out /
Change )

You are commenting using your Twitter account.
( Log Out /
Change )

You are commenting using your Facebook account.
( Log Out /
Change )

Notify me of new comments via email.

You have been automatically moved to the Trans version of XVideos. To stay on the Straight version, click here .
To disable category changing alerts, click here .
12 min Curious Porn Pass - 140.4k Views -
15 min Curious Porn Pass - 59.7k Views -
13 min Curious Porn Pass - 481.5k Views -
18 min Misscummymouth - 230.9k Views -
14 min Curious Porn Pass - 258.4k Views -
6 min Transsensual - 589.8k Views -
10 min Curious Porn Pass - 101k Views -
10 min Barebacked - 430.1k Views -
1 h 36 min Xtime Videos - 1.4M Views -
14 min Curious Porn Pass - 54.4k Views -
22 min Shemale Mall - 1.2M Views -
10 min Barebacked Shemales - 47.1k Views -
6 min Daughter Swap - 607.6k Views -
28 min Horny Porny Trannies Journey - 193.9k Views -
8 min Ladyboysheaven - 484.2k Views -
5 min Ts Playground - 434.8k Views -
XVideos.com - the best free porn videos on internet, 100% free.

See all models online at LitWebcams
Swipe to see who's online now! Close
A special evening experience turns into a lot more.
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.
You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.
My husband Dan and I have always had a great sex-life, but with the day-to-day pressures of working and trying to make ends meet, we weren't always up for it or in the mood. Because of that, we had made a promise to one another early on, that at least once a month we'd have what we called a "special evening". It was something the two of us looked forward to without fail.
Now don't get me wrong. We always went out once a week, either to a movie or to dinner or both. But that wasn't what we'd meant by having a special evening out together either. Those nights were meant to be above and beyond whatever else it was we enjoyed doing together in the bedroom. In the beginning, it was more along the lines of touchy-feely stuff with one another in public or semi-public places. Just doing that inevitably got us both fired up, and it wasn't often we even made it back home to spend the night fucking there. We'd actually done so in the backseat of the car at one or bar parking lots we had driven to. Surprisingly, as a young woman fresh out of high school, I'd never even done that. Plenty of heavy petting yes, but I'd never fucked any of my back then boyfriends in their cars. When I did it, I wanted to be comfortable in a nice soft bed, not cramped up or twisted into a pretzel while my boyfriend got HIS rocks off. Needless to say, it was a bit of a surprise to find myself actually being turned on by finally doing that.
So it was that our once a month adventures naturally got more and more erotic, and at times a bit more dangerous and exciting too. The previous month we had ventured into yet again a whole new level of acceptance and excitement. We'd talked about what happened long into the night afterwards, fucking wildly between that discussion on and off until we both finally fell asleep totally exhausted. We'd ended the evening in agreement that our "Special night" after that could include just about anything.
At thirty-eight, I considered myself still reasonably attractive and younger looking than my age. Dan of course told me I looked as good, if not more so than most women in their twenties. But he was prejudiced of course, especially when it came to my boobs. Dan had always been a breast man, and made no excuses for it, ogling and enjoying any woman who he thought had a nice rack. I didn't mind his looking either, or even occasional touching or fondling as it turned out, I enjoyed ogling more than one man, and even the occasional woman myself.
I had reddish brown hair that fell well down to the middle of my back, once again Dan having a thing for women with long hair. I had very often jerked off his cock with my hair in fact, something he quite often enjoyed my doing. With fairly large nicely sized breasts, a good C cup, and very sensitive nipples that when he played with them nearly brought me off to orgasm in just doing that, I gave Dan access to my breasts just about any time and anywhere he had wanted. It had been his doing that which had led to what happened the last time we'd gone out for one of our special evenings. And we both knew afterwards, there would be no going back.
I had worn one of my "cum fuck me dresses" for that evening, something I really enjoyed doing just for Dan. It gave me the opportunity to dress up in something I wouldn't have normally worn out in public. And because of that, Dan and I usually went someplace a bit more secluded or exclusive than we might normally do. This time I had worn a dark green emerald wrap around dress. I liked the way I looked in it, and the way it accentuated my long reddish brown hair. Cut the way it was, it gave me a fairly deep plunging neckline for one thing, but for another, with the wrap cut the way it was, it also gave Dan fairly easy access to my breasts. We both loved how he was able to slip his hand inside cupping either one of them, fondling them to his heart's content. Something he enjoyed doing while we sat at our table waiting for our dinner to arrive. Slipping his hand inside briefly between visits from our waiter, once or twice just barely having removed it, giving our cute sexy waiter a bit of a thrill perhaps, knowing what Dan had been up to. But the other thing about my dress that I also liked, it was also very short. It provided him the same easy access to my pussy that he had with my breasts, especially as I wore nothing else on beneath it. So when I say it was a "cum fuck me" dress, it truly was in every sense of the word.
This particular evening, we'd been sitting in a booth enjoying our dinner together having just finished, and now sat enjoying the remainder of our wine. By now, Dan had his hand between my legs and had been slowly fingering my very went cunt for the better part of the last fifteen minutes. Twice I had nearly climaxed with him doing so, though he'd purposely backed off both times, his intention of keeping me damn fucking horny, which I was. During dinner, we had noticed a somewhat older gentlemen sitting alone at a small table across the way. It appeared obvious to us he was more than likely there alone on business as he had some paperwork sitting next to him that he'd early on been going through. During his dinner and ours, he had taken notice of us sitting there across from him, and had even smiled once or twice, with Dan and I smiling back in return. It had been because of that, we'd found ourselves slipping into what became a rather erotic naughty conversation, not to mention some obvious exhibitionism that slowly got bolder and bolder as we sat there. The gentleman soon took notice of it, and continued to smile, occasionally nodding his head in approval towards us as Dan once even revealed one of my large breasts briefly, much to the man's pleasure and amusement. We'd been having so much fun doing that, I actually found myself somewhat disappointed when the gentleman eventually stood having paid for his dinner and prepared to leave. He had come by the table on his way out however, and had said simply, "You have a very sexy wife, and I enjoyed watching the two of you," he'd said and then left before either Dan or I could even comment.
With each of us both so horny by now after our near constant teasing of one another all through dinner, I knew then there was no fucking way I wanted to wait until we got home. But I wasn't in the same mood to finish this out in the parking garage inside the car either. As though reading my mind, though Dan was every bit as horny as I was, we then decided to see if we could get a room for the night there at the hotel rather than going home. As we walked out into the lobby, it was a surprise to see the same gentleman we'd seen earlier, once again a few papers spread out on a table as he sat glancing down at them.
"You in the mood for something really naughty tonight?" Dan asked me as we stood there for a moment prior to walking over and securing a room for the night.
"What do you have in mind?" I asked, hoping it was what I had in mind now as he said that.
Though we had on numerous occasions actually discussed the possibility of including either another man or woman in our special evenings out together, so far we had never done it. Mainly because the situation hadn't really presented itself. It wasn't as though we really knew anyone, nor did either one of us feel in our respective positions at work, that we could very easily accomplish doing that either, until now.
"I was thinking that it might be fun for you to put on a little show for the two of us," Dan told me. He knew that one of my fantasies had always been to do a little erotic exhibitionism, dancing, touching and playing with myself while a total stranger watched. And hopefully in doing that, would become aroused enough to sit there and stroke himself off while I did. I wasn't as sure yet about going much beyond that, but the thought and image of seeing this particular man sitting there doing just that, was at the moment at least, a risk worth taking to find out.
"You actually thinking about asking him if he'd like seeing that?" I asked.
"Sure...why not? If he says no, we just get the room and have fun anyway, no big deal. But if he says he's interested, and willing to let you call the shots, then why not?"
I knew by Dan's having said I'd be calling the shots, he was basically giving me permission to do as much as I was comfortable with, though at the moment, I wasn't sure to what extent that might be as yet either. Deciding a great deal of that would be dependent on how the guy reacted, if I got more aroused than I already was, and if I felt like I wouldn't be coerced into doing anything more than what I felt I could consciously do.
"Stay here," Dan said not giving me much of an option, though I felt a sudden tingle of thrills running up and down my spine as he walked over to where the guy was sitting. I stood there watching for a moment as they spoke, the gentleman suddenly looking up in my direction with a wide-eyed smile on his face as he nodded his head, and quickly began gathering up his paperwork. As soon as he began doing that, Dan headed over to the lobby's check-in counter as the man approached me as I stood by the elevators.
"Since we've not been properly introduced as yet, my name is Jerald," he said politely taking my hand.
"Susan," I said in response to that, though I'd already made up my mind about not giving him my last name, though I had noticed of course, he'd not given me his either. "Pleased to meet you," I added blushing a little as I stood there, wondering now what all Dan had told him.
"Like I said earlier, you are indeed a very sexy looking woman, and I am both pleased and surprised that you two decided to allow me the pleasure of seeing you dance naked," he informed me.
I knew from that, that Dan had probably promised him very little else, leaving the rest of what was to happen, or not happen up to me once we'd reached our room.
"Thank you," I responded back. "And I hope that if you enjoy the performance, you won't feel embarrassed in doing just that while you watch," I now added dropping what I thought was a subtle hint at what I hoped was something he would do for me at the very least.
Once again he smiled broadly, his deep blue eyes offset by a bit of silver coursing through his hair, reminding me at once of my father in a way, which at the moment however, was a strange thing for me to be thinking about. Especially as I was now looking forward to seeing him stroking his cock as I danced.
Dan soon rejoined us, and then the three of us rode up in the elevator together to our room. Once inside, Dan made himself immediately comfortable, more or less setting the tone and the mood for Jerald. Fixing us each a drink from the bar, he then found some soft, sexy music on the radio, which I almost immediately began swaying to there in the middle of the room. Having always been a bit of an exhibitionist, I was getting more and more turned on as I did so. I knew full well I couldn't exactly do a strip-tease as I was only wearing the dress with nothing on underneath it, but I also knew I would work that to my best advantage nonetheless.
With Dan and Jerald both now taking seats as they sat watching me dance, I proceeded to tease them a little with a flash of skin here and there, eventually baring a breast briefly and as seductively as I could, gauging their reactions. As hoped for an expected, Dan was certainly aroused and hard as hell as his obvious stiff erection poked against the material of the slacks he was wearing. At first, I saw no noticeable bulge in Jerald
Chanel Preston Squirting
Lily Labeau Fucking
Kinky Sex Forums

Shemale Experience

Report Page