Finally, I moved to a city that was exciting, Miami. I moved to Miami looking for something new and adventurous. I grew up in very conservative town where nothing exciting went on. In Miami I found different languages, gay people, different ethnic persons, art, and culture. However, my job keeps me too busy to have any kind of social life.
After about a month, I went out to a bar on Washington Avenue, a little hole in the wall, but it was backed. I really didn"t have any no-work friends. I lived in South Beach, so it was an easy walk to Washington Ave. The week I had was long long long, so I decided on drinking alone or with whomever I met while I was out. I try not to get in rare form hanging with the office personnel. So alone I was.
After about two or three beers and girl sat down with me. She was dressed in jeans, a nice little top, and looked pretty hot. She was Hispanic, soft skin, nice face with pronouned features, brown eyes, long black hair. She was about 5 foot 9 with her heals. This was a pretty hot chick after glancing a couple more times.
As always, it"s too good to be true for a hot girl to sit down and just start talking to you. So, a guy sits down. Another beer.
After my next beer came, the two began arguing in Spanish. The guy looked pretty upset, they went outside, left their drinks, didn"t pay and just walked out. Well, half way through my drink she comes back huffy puffy on the angry side and she ordered a dirty martini.
I asked her, guess that date didn"t go to well? She said no, in a very raspy, hispanic accent, and somewhat deep voice. She said I"ve never seen you here, where are you from. This caught me off guard, I expected no coversation. Additionally, her voice was sexy, deep, husky, yet I couldn"t put my finger on why it alarmed me. Also, she seemed to recover from her ordeal with the last guy. I told her my story, still trying to figure her out.
After conversing for about 20 minutes about life in general, I figured out that this was no chick. Sure, she was hot, but I was pretty sure this was a male. The voice, a slight lisp. She sounded feminine, but then I could see at close look, she was a he. Somehow, that excited me. I mean she"s hot.
So, after we were both a little intoxicated, I asked her "are you 100% female?" Taken back a little, she said, no that was what caused the fight I had earlier.
Well, this led into a barrage of drunk questions about anal sex and blow jobs, neither of which I had done with another man. I told her that a past girlfriend would like to finger my asshole and sometimes use her vibrator while having sex, and I admitted it was pretty erotic. She said "wow" you should try anal sex, it"s wonderful if it"s done right. She said, I would have no problem deflowering you. I turned down the offer. I mean, this is a hot girl - but it"s a guy, my stomach ached w/ butterflies thinking of the offer.
Drunk as I was, I could not bring myself to it. I am straight. She told me her name was Adrianna, gave me her phone number. She said her job was looking hot and selling property in Miami. Apparently, she was left a fortune at her parent"s death. That would explain how she got the money to get the surgery and hormones necessary to look hot. Nice breast implants, c cup, not too big. Skin supple and very soft looking, nice full lips, high cheek bones, and bedroom eyes. Along with her accent, she was hot. I gave her my number and went home. We ended with saying we"d go out again as friends.
At work the next day, I could barely concentrate thinking about crossing that line - hooking up with a shemale. I got home that night, looked up some shemale porn, and jerked off hoping to rid myself of this urge. But, it just got worse, while masturbating I began imagining her slowly entering me with her cock. I imagined she had a nice soft, cut cock. I began fingering myself until I had an orgasm.
The next day of work, her number was in my pocket, I was so torn should I call? Then at lunch, her call came through to my cell phone. It was Adrianna. I almost did not answer it, because I was scared of what might occur. But, I answered it.
"I went shopping today!" was her first words. "I got you something she said." "It"s a suit - you said that you were looking for good suits when we talked, so I figured I would pick one out for you from my friends store." I said "wow, thanks you didn"t have to do that." She said, come over tonight after work, "I"ll give you the suit and if you"re luck I"ll give you a massage." I was hard just thinking about the idea. I accepted. I thought it was kinda wierd buying me a suit and all, but I wanted to fall right into her trap. I wanted her to seduce me.
On the way home, I kept going back and forth. I was hard a rock just thinking about this, but maybe I should just leave it a fantasy? What if it was a really bad experience, am I turning gay? No, I"m not gay, but I gotta see what happens.
I got ready and arrived at her condominium in South Beach at 9:00. She answered her door wearing a light pink skin tight summer dress. It was loose at the bottom, but tight around the waist and the top. You could make out the image of her G-string through the cotton dress. Her breasts were set within the dress very nice. I could see her soft tan and hispanic skin on her chest. She smelled like fruit this time, very sweet. I never realized she smelled this good. But then again, I was at a smoky bar last time we met.
She had a beautiful 3 bedroom condo right on Alton Road near all the action. For those non-Miami readers, trust me Alton Road near South Beach is an incredible place to live. Her condo was on the water, swank furniture. This chick was either loaded or really did run into a fortune. She let me in immediately showed me what appeared to be an Armani suit. Nice suit, I normally wear Brioni or Zegna, but Armani was not bad. She poured red wine and said try it on!
She sent me into her bedroom bathroom to try it on. Her bedroom was amazing. It was huge, and opened into a bathroom. The bathroom was all glass stainless steel and marble. Immaculate, elegant. But the kicker was that she had a spa and bay widow in the bathroom which overlooked the intercoasta waterway. If you were a voyeur on a boat, this chicks place would be a prime target.
I tried on the suit, it fit, but needed some tailoring. I went out and showed Adrianna. She liked it. After changing out of the suit. We sat down, she had some stuff to eat, finger food, and we drank a couple glasses of wine. Again, she was easy to talk to.
The conversation again turned to her inquiries about me and anal sex. She asked what kind of vibrator my girlfriend used? I told her, a small one, hard plastic, looked like a torpedo. She crossed her hand, staring through me. I know she knows that I"m hard as a rock in my pants. At this point, I could feel precum dripping from the tip of my cock, I was so horny for her.
She then said, have you ever kissed a boy? No, I said. She said, so you"ve never done anything with a boy? No, I said, and I was being honest. She said, darn I wish you were into boys or girls like me. I don"t know where she was going with this, but after a brief silience, she changed the subject.
She said, "my only claim to education past high school is massage school." So, before you go, I insist that I will make your week better after I give you a massage, full body. I said "I don"t know, I"m not comfortable being naked, even for a masseuse." She said, "Silly, I"m not saying naked, just wear your underwear." She giggled at me. Fortunately, I was wearing boxer shorts, so this wasn"t a problem. The problem is that I had a hard on, and I wanted to hide it. I think she sensed that somehow.
She took my hand walked me to her bedroom. I willining accepted. She had a king size bed, very low with an Asian platform look. I had managed to calm my excitement down, drinking down one more nervous glass of wine.
While facing the bed with her behind me, I kicked off my shoes and socks, slid off my jeans and my tee shirt, dropping them at my side. She was in the drawer behind me grabbing massage oils - that"s what she said anyway. I had a fully erect cock at this point, so I didn"t turn around, I just laid face down on the bed w/ my shins hanging. I noticed that my cock was wet with precum. I was excited, somehow very intensely, by this shemale.
She hiked up her dress and straddled my back, immediately pouring a lotion or oil on my back that was warm. I could feel her warm soft inner thighs on my sides. She started with my back and moved down my back until her crotch was straddling my ass. She was working my muscles and spreading the oil. I could hear her starting to breath harder and I could feel her making suttle motions with her hips driving them into my ass. For the first time, I confirmed that this was no girl. I could feel her hard cock resting between my ass cheeks.
She must have had on lacy silky panties, but cause as she picked up the rythm doing my back and lower back with her hands, her cock was slowing sliding up and down. I was literally having butterflies, I was probably trembling in my thighs and precum was leaking out of me like a faucet. I was more turned on now, than every in my whole life.
She moved her hands down to my ass and moved her hips down to my legs, still straddling me. At this point, she said "My dress is getting oil all over it, do you mind if I take it off?" I said "well, that"s fine." She then said "look, I know you"re straight, so I don"t want you to think anything, it"s just an expensive dress, if you want me to stop the massage that"s fine, but I don"t want this dress ruined." I said no, my voice shaky, that"s okay.
After removing her dress, she was in a little g-string with a bra. Her g-string was white silky and lacy around the edged as I thought it felt like on my back and ass when she was straddling me. I peered behind me, while I hiked a couple of pillows under the my chest so that my head and upper body were propped up a little. For the first time, I finally saw her panties bulging out with a hard on. Her panties bulged out and I could see the outline of her rather large cock behind the veil of silk and lace. I could see her ball sack slightly showing on the edges of the skimpy panties. This was indeed a shemale.
She began massaging my ass through my boxers. "I can do this better without your boxer shorts, can I hike them down?" I said "yes." She slowly hiked down the boxers, poured oil all over my ass crack and ass, then began kneading it. I could still feel her hips gyrating as she massaged me. She slowly moved her fingers suttley over my ass hole, then down to the soft spot between my asshole and balls. She used two fingers to massage that area and I willingly spread my legs apart for her. At this point, she was breathing deep and hard, I caught myself moaning.
At that point, she said "you"re really turning me on, you should probably leave now or I"m going to cum all over you tonight, I can"t take this." I was silenced, for some reason I did not want to verbally admit that I wanted to screw her in a big way. I said, you"re okay, I"m enjoying this keep going. She said, well the next part of the massage is your chest. So, you need to flip over. She pulled my boxers back up and slowly took her weight off my legs and turned me over.
She then exposed my hard on through my boxer shorts. She said, "looks like I"m not the only naughty one." She could see the cum spots on my shorts soaking through. She was really hot, perfect stomach, nice full hips, beautiful c cup tits, luscious tan skin. Her black hair was down and her full lips looked wet. She continued to bite her lip and half smile at me as she began massaging my chest.
At this point, her hard penis was pushing against mine, they were side by side. She continued the massage a little longer, than said "I can"t take this, I want to taste you." As I said, "you what she quickly went down and engulfed my cock in her mouth. I was laying down face up, she was then laying sideways, as she took my shaft deep into her throat she move her hips over and eventually my head was between her thighs.
I could smell her body odor, a thicker smell than women. She gave off an odor that was sexy, I wanted to get closer to the smell of her crotch. Meanwhile, I was fighting back an orgasm. "Oh you taste so good, you"re giving off so much come, I love it" she said. I could hear her slurping my cock in and out of her throat.
She removed her panties and purposely left them on my face, I think she knew I loved her sexual smell. I now could see her exposed penis for the first time. She too was dripping with precum. My face was closer to her balls and asshole, so I shed my shackles of society and dug my tongue into her asshole.
As I slip my tongue into her ass checks, her body shivered and she moaned. "Oh God, I"m sharing everything with you tonight" she said. "Do you want me to share everything with you?" Yes, I said, I was so horny I"d do anything to please her.
She then stopped turned around, and began deep kissing me. Our tongues grappled with eachother in a deep rythm, both our mouths were wet with saliva, we were both hungry. As she straddled me I could fee her hot shaft against my stomach and my cock was resting against her wet asshole. My natural reaction was to motion my cock into her ass hole. Her cock on my stomach was burning hot and wet.
She said "no, me first." She spread my legs opened them up, hiked my legs up, grabbed a bottle of what I think was some sort of sex lotion. This was planned, she had some lubricant there.
She took her large 8 inch cock and pushed it against my asshole and ball sack. She said "I will show you how to make this feel awesome the first time." She grabbed my cock, which was about to explode. Good thing I had 3-4 glasses of wine, or I"d have lost it a long time ago.
She said "relax" and I"m going to rub your cock. I want you to close your eyes and just imagine me deep inside you, then slowly work my dick deep into you." "Don"t go too fast, just allow the pleasure of the sensations on your asshole open it up and let it in." I took her advice.
She came up and began deep kissing placing the head of her cut cock and placed the shiny head under my balls and against my asshole. She was moving it slowly. She then stopped kissing me grabbed my cock and slowly massaged it as her hips slowly and gently gyrated working her cock into my asshole. I moved my hips and could feel with each small thrust the head of her hot cock slipped a little further. There was a little pain, but her hand job felt awesome. Eventually, I began moving my hips further and the handjob got more intense. I wanted her deep in me, I wanted it bad.
At one point, I could feel the head of her dick finally burst into my ass. The head finally worked it"s way in and immediately she pulled it out. She then came down and began deep kissing me. At this point I could feel her penis drive slowly in again. She was now moving her hips very slowly and her hot thick cock began filling the walls of my ass moving up. She was breathing extremely hard now our tongues dancing and wrestling. I was in total extasy. I wanted to jerk off, because this was so exciting I feel the need to cum, but instead I pulled her close and allowed her to make deep thrusting motions into my ass. My ass was fully opened up now, I could feel it slid up into a spot behind the wall of my ball sack and it continued to hit causing intense pleasure. I could feel that the asshole was hurting, but this mixture of pain and intense pleasure made me driver my ass against her cock.
She was now thrusting fast and deep. We were tongue locked kissing deep and hard. Then she pulled out and quickly told me to get into doggy style position. I complied.
She slowly entered me again from behind. She was now going to town, she was penetrating me with her full length. She said "I"m going to cum, I"m going to cum, taste me please taste me!" She was moaning and her accent ever so raspy, I felt I had to comply.
This I never thought I"d ever do. She pumped my ass a few more times than slammed down on the bed on her back and she was massaging her own cock. Her cock was covered with my ass, it was shiny, thick, the head was well defined. Without hesitation, I went down on her and began giving Adrianna a blow job. She was humping my face slowly and took her balls and began cupping them and moving them with the motion of her rythm. Her cock began to stiffen in my mouth.
She was now moaning with pleasure, I could literally see the veins bulging when I stopped to look. Then I engulfed her as deeply as possible and felt my mouth begin to fill with a small of amount of hot semen. It was salty, but mixed with her strong musky sexual smell that was emanting from her ass and crotch, I began trying to give her an orgasm. Finally, she began moting my head down harder and her cock began pulsating, and then without warning the semen began to fill my mouth and I swallowed it and craved more. There was no reason, I just wanted to cum and I wanted more of her.
At that point, she threw me down on the bed again, her cock dripping wet with semen. She grabbed the lubricant and covered her ass hole. She then inserted my cock into her ass and again we began kissing deeply, she was breathing hard, and then whispered "cum in me, cum in me, please cum in me." This was no problem, I then pulled her hips down onto my aching penis and deeply began close humping her ass hole until the cum began pouring out. She was moaning loudly and began saying "yes, yes, more." The cum was dripping out of her soft ass hole over the sides of my cock. I must have came for ten seconds as I kept working the semen drenched cock deep in her ass. Thrust after thrust, I was pumping my semen into her.
Shortly after, I pulled out and she crumpled to the bed. We were both breathing hard. It was then that I realized what I had just done and I regretted it in some way, the way you regret it when you have that one night stand with the girl you didn"t want to shag, but alcohol made you do it.
She said "I knew I could seduce you, I knew it." We cleaned up, put on our clothes, and without a whole lot more converation, I went home. My asshole sore, my cock sore, I had just realized I had sex with a shemale without a condom, was I out of my mind? When I got home, I showered and took the next day of work off. I swallowed a male"s semen, gave a blow job, had anal sex with a man, and I didn"t know how I felt about it. Lastly, was I diseased now, what an idiot, how could this happen? It is very weird how one can have such an intense animal instinct for an sexual encounter, wherein you abandon all reason, then how reason comes back to you and stares at you with the scorn of your mother when you were a kid.
This is not the end of this story. I had two more encounters with Adrianna. Now, she wants to have a relationship. Adrianna and I don"t have any diseases, I was very lucky. But, I do have to make a decision whether I would actually date a passable shemale who has no interest in losing her dick. She"s hotter and cooler than most girls I"ve dated, yet I have no idea what to do.
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