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My First Shemale
Early May 2006 or 7, standing on the northeast corner of 46th and 3rd, a rather nice New York City day, except Belinda wasn’t answering her phone for our 3 pm “appointment”, and I was not keen to just hang around smoking cigarettes on the corner wondering if I had been stood up. I had no prior experience but it dawned on me shemales, especially shemales for hire, might not be the most dependable group of people, well, maybe if they were a shemale cop, that thought hit the erogenous spot of my brain and triggered a pleasant mental picture of a leggy blonde, maybe 30 years old, in a short navy blue dress with front buttons all the way up and all the way down, with stockings and garters to boot, maybe leather knee boots. But there I was, waiting for Belinda, wondering if her ad was a fake, she was just jerking me around, maybe setting me up for a mugging, or maybe she was just very undependable. I thought, crap, I had had all the options for sex time in NYC and I may have wasted them on Belinda.
But after about 15 minutes and several Marlboro Lights, my phone rang, and it was Belinda returning my calls, running late, had visited a client in Washington, D.C., the train was late, did I still want to meet, and hers was a basement level, street entrance apartment, just down the block on the other side of 46th. And so it was. Tossing out the spearmint gum to offset my cigarette breath, my knock was answered by a blonde bombshell, maybe five foot three, in translucent harem pants, a tight cream short beginning in a V several inches below her navel, just above her mound, ending just at the crease where her thighs joined her torso, with just a bikini bottom back, gold colored sandals and an emerald green sequined brassiere. Her blonde hair was mid-shoulder in a ponytail. I had found Genie, or Aladdin, or something! I didn’t know if I got to rub her lamp, but already my penis was conducting its own campaign of wishes. This definitely was a she thus far, and if a male was in there, it had not made an appearance thus far.
“Please come in, I’m sorry, the train from DC was late, you are my only appointment this afternoon, we won’t cut your session short, may I get you a glass or water,” she said. I stared, did I mention her eyes were deep brown, lashes black and long, a straight nose, kissing lips with a pinkish lipstick. Her cheeks were blush with just a hint of gloss. “You can put your roses over there”, Belinda pointed to a short end table, “Is this your first time?” That was the dreaded question, I was a rookie, I did not know what happened, I had seen pictures and videos but never a transsexual woman in person, never seen a real she dick, or clitty, or whatever you wanted to call it. I had dared myself into this, a bit bored with hetero tits and pussy perhaps, especially marital pussy, wanted some “strange”, and türkçe bahis maybe this is as strange as strange gets. But it appealed to me, all the best parts of both, womanly face, lips, breasts, skin and a cock, the forbidden fruit, the demarcation point, maybe not so straight after all. Shemales had, after all, been getting my dick hard vicariously for some time now, as I imagined sucking those cocks in the porn I had watched. And maybe I had more feminine side than I thought, curious what a woman feels with a hard cock thrusting in and out of her vagina, caressing her clitoris, bringing her to orgasm.
“Uh, no, I mean, yes, this is my first time.” And what do you want? What do you expect? “Well, you are more experienced in this than I am. Surprise me.” And so, Belinda suggested a massage. I stripped and lay on my stomach on a futon just beyond the beaded curtain separating the two small rooms of her New York studio apartment. Although I did not then know it, she, too, disrobed and began a gentle conventional massage of my legs, spending time on my thighs and glutes.
As a massage it was adequate but unmemorable, too light generally, when suddenly I noticed something new against my thighs. Even unseen in a massage, one recognizes the massager’s body parts, hands, of course, but also when legs press your skin, or perhaps a breast that tickles as the giver leans over, elbows or forearms digging into muscle. Perhaps a masseuse even pressed her mons against your body as she stretched to reach your far shoulder. This new sensation was not that, not that at all. Clearly warm, soft, not muscular, pleasant, though. It must be her cock, but it is really soft, not like mine starting tumescence, just rather warm and dry. Her advertisement said she was fully functional; I wonder if she is not. She moved further up my back, I reached back behind me with my right hand, and found her package. I took her cock in my hand, not large, smallish diameter, but this thing is very warm. This would be great in a coat pocket on a winter day, might want two, one for each pocket as handwarmers. Weird thoughts. Also, so much for my passivity, first time, maybe, but I have done this many times in my minds eye. Let’s get on with the adventure.
Belinda murmured, “Do you want to roll over, honey?” I absolutely did, nothing much was going to happen with my face and cock planted on her futon. As I rolled over, Belinda slid fully up my body so we were now side by side, faces close. And she kissed me. My cock was fighting to take over my brain. I kissed her back, and reached up to caress her right breast, maybe a C cup, very nice, soft, I could not feel an apparent implant. Her nipple, hardening, smaller than a pencil eraser. I planned to take it in my mouth, but Belinda had her wet lips on mine and her tongue was sliding across my teeth, teasing my tipobet güvenilir mi tongue, so soft, so wet, so erotic. Whoa, this is really a guy! But she is the best kisser I have had in a very long time, and it feels so very good, so sensual. Call me queer, but this is heaven, her tongue in my mouth, then mine in hers, each teasing tongue and teeth, and sucking a lip gently. I should have done this long ago, I am not getting this kind of passion at home, fuck it, I really want this!
I had been caressing Belinda as we kissed, cupped her breasts, sucked her nipples, drew circles around them with my tongue, my hands exploring her glutes, her thighs, her belly, across her pelvis, and then I took hold of her cock, now about six inches long, still narrow, but fully erect, as was I. I held this dick and it seemed strange, and I gathered this was because while I have held my cock for probably thousands of hours since I was 12, the sensation was solely tactile, how it felt warm and stiff but with a soft layer of skin with a solid core but I lacked the erotic response that I got from my own cock. Well, duh, it ain’t my cock! That rather changed when Belinda took hold of my tool and we mutually stroked in unison, our tongues still enmeshed.
Belinda broke off, turned to the side of the futon, returning with two condoms, sliding one down my cock first, and then over hers. Well, I guess I will be wearing a raincoat, I thought, this might be smarter, AIDs was still a life sentence, then Belinda said, “Do you want to suck it, baby?” I did, thinking she had forgotten my name, fuck, who cares? She turned around, her thighs to my face and held her cock out toward my mouth. Damn, here it is, truth or dare, go big or go home, it’s what you came her for. I took a condomed cock into my mouth for the very first time. Condom didn’t taste like much, and now it was slippery against her cock and a little rubbery in my mouth, but I was giving a blowjob and decided to do it right. I sucked, and tongued, and licked her shaft and took each of her balls gently into my mouth, caressing each before taking her cock back in. I cheated some, using my tongue to push the condom up her cock so I could get my mouth onto her shaft, taste her and feel what a bare cock feels like in my mouth, careful not to fully push the condom past the helmet of her cock. Belinda, if this was past the limit, merely moaned, and pushed her cock closer, raised no objections.
I then felt Belinda take my cock with her mouth as she began fellatio on me. Sensation was a little dampened through the condom but quite familiar and welcome. She blew like she kissed, her tongue teasing my cock. My attention focused on my aroused tool, I perhaps started to fall a little short on my own sucking. Sixty-nine had never in my heterosexual life been my favorite thing. Either perabet güvenilir mi you give all your attention to your partner or you are a selfish dick (literally), and I think it is all a little distracting, overrated, nothing wrong with taking turns, does not need to be the whole ballgame, take it like innings in baseball. One half inning you are in the field, the other half inning, you are at bat. Same with oral. But hard to play nine innings before a home run!
I felt I was starting down the final stretch to orgasm, not immediately, but it was on the glidepath, seventh inning stretch to return to my analogy, at which point Belinda asked, “Do you want to top or bottom?” I had not thought this through, I think we were no longer in baseball inning metaphor, and stammered, “How about we take turns at both?” She responded, “You will like this. Raise your ass onto this pillow, rock backwards onto your shoulders, and pull you knees back as far as you can.” “Actually, a bit more, there,” and she began to caress my anus with two fingers, increasing speed slowly. I could feel lube, and I could sense my sphincter gently relaxing. Belinda’s now had one, then two fingers, probing my asshole, and I could feel them against my prostate, quite nice. She withdrew her fingers, sidled up against my thighs, taking her cock in hand and pressing her helmet against my open anus.
Her cock partly in my ass was certainly not unpleasant, yet as she began to press her dick further into my ass, I felt a bit of discomfort, I guess at my inner sphincter, not certain of the anatomy, and Belinda paused. Holding position for about 30 seconds allowed my ass to accommodate her cock. I could feel her cock fully up my ass and her testicles against my glutes. Belinda began to slowly stroke, pulling back but not out, stroking back in. This lubed cock felt pretty good, my prostate was being massaged, I had these fine tits bouncing in front of my face, and then Belinda began stroking my cock in time to her fucking. Oh, this must be what it feels like to be a woman getting fucked. I liked this, a lot. “Fuck me, Belinda, fuck me. Fuck me harder, I want you to fuck me”, apparently losing all vocabulary other than that necessary to have Belinda fuck me even more. “Oh, god, Belinda, fuck me. It feels so good, I want you to fuck me!”
Just a few minutes I guessed, and Belinda began heavy breathing, I just kept up my “Fuck me, Belinda”, totally and solely into that moment, and then I felt Belinda spasm and moan while still stroking my cock. When she came, it sent me over, and I blew cum up to my face, onto my chest and belly, hot, white and all over myself. “Oh, your ass is so tight, that felt so good! I can’t believe how much I came” she told me. I couldn’t believe, not telling her, how good getting fucked in the ass felt, surprised myself, and determined to do this again sometime. I mean, it can’t be gay or something if she has tits. I have been back to New York many times, have not hooked up with Belinda again, but I have succeeded in getting my ass fucked again. Belinda, though, will always have my cherry ass.
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