How I Met Alyssa

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She gives my ass a little slap, "Of course, you got mine, so I'd like it if I can have yours, unless-"

"Don't worry Alyssa, you can use my ass all you want," I interrupt her, "like you said, it's only fair and I am quite ... curious about it."

Her smile reappeared, "Good, I'd like to try that with you. Are you ... clean?"

"Yeah, I happened to clean myself before I went on my way," I reassured her. "What a coincidence huh?" I asked with some sarcasm

"yeah, unbelievable," she answers with a smirk, "now bend over. I wanna inspect the goods."

Her forwardness made me smirk, but I was happy to comply and bended over. "be gentle with me my love, it's kinda unused so far," I said. I hadn't had anal sex before, well not on the receiving end anyway.

"Owww, you remained a virgin for me down there?" she said in a naughty voice, her finger rubbing around my ass, while the water was spraying against it.

The stimulation made me moan a bit, it felt kind of nice, "Yeah, just for you, for your pleasure."

"Hold up, if we're gonna have some fun like this, I'd prefer if we did it somewhere else," she suddenly says.

I looked back, "What? I thought you wanted to fuck me?" I asked, a bit confused.

"Don't worry baby, I will, but I'd prefer if we did it on my bed, more comfortable," she says.

I nod and agree with her. We get out of the shower and dry ourselves off, doing our best to ignore our boners. I am about to ask what clothes we're gonna wear, but quickly realize it's a dumb question, as what we're doing doesn't require any clothes. We quickly get out of the bathroom, dry, clean and ready for more action.

Alyssa leads me to her bedroom and I'm once again a bit surprised by her house. It's kind of what I expected of her, a big bedroom with a king size bed. It could be easily be described as 'girly', but not enough that its childish, just feminine I guess. This time I don't lose much time staring at the furniture and simply join her on the bed. At the moment we sit next to each other, looking at the other one.

"Ready for some more fun?" she asks excitedly.

"Sure thing, how do you wanna do this?" I ask her

She thinks for a moment and then gets an idea, "I know! How about you lay on your back and I lay on top, we blow each other and I also prepare your ass as well. After that I can fuck you alright?"

Wow she sure is enthusiastic about this, but who am I to complain? "Sounds good baby," I tell her, giving her a smile.

I lay down on the big bed, waiting for her to join me. She turns herself in the right way and crawls over me. I see her flaccid penis hanging in front of me and it was pretty hot. Alyssa didn't waste any time and immediately went down to business. She took my also soft dick in her hands and start licking it. I was uncircumcised, so was she by the way, and her tongue felt pretty good like that. I was almost too lost in my own pleasure to realize I had a job myself. I grabbed her ass cheeks and pulled her closer to me, taking her entire dick in my mouth, balls deep. Her balls almost rested on my nose, and I happily licked her entire dick in my mouth. I felt her dick gradually grow and harden in my mouth, to the point where I had to release it. By now it was about the same size as earlier, completely erect. I still had some trouble taking it completely inside me. I make a mental note to 'practice' a bit in the future, one way or another. On the other side of the 69, Alyssa sucked me to full erection as well. My cock was once again throbbing hard and ready for more action. Too bad I was going to get a bit less. She bended my cock and lowered her face further. She briefly licked my balls, a few long licks, but soon lowered herself further. I felt her hot tongue on my asshole, which made me moan.

"ooh damn, that feels ... kinda nice babe," I whisper around her cock.

She grabs my ass cheeks and spreads them to have better access, "Nice feeling isn't it?" and she goes back to licking me, preparing me for the upcoming fuck.

While sucking her cock, I notice her tongue movements are similar to mine earlier. Either It must have felt really good or my I must be a natural. I squeezed my eyes shut for a moment, when she inserted her tongue inside my little asshole. I wanted to moan, but couldn't because my mouth was full of her dick at the moment. I didn't bother getting her out of my mouth, just kept on heavily sucking and licking her cock.

After another few minutes of sucking and licking each other like that, she lifted her head and said, "I think that's enough baby. You're wet enough and I don't wanna cum in your mouth."

I got her throbbing member out of my mouth, "Ok." She rolled off me and I got on all fours, my ass pointing at her. "Like this baby?" I asked.

"Perfect," she simply said, her hands grabbed my hips like I did earlier. It made me cringe a little, as I'm not really used to being handled this way. "You okay baby?" she asked.

"I'm fine, go ahead," I assured her.

I didn't hear anything else from her, but prepared myself for what's coming. I feel her cockhead prodding my ass and with a swift push, she inserts herself in me. It made me cringe a bit, but after a combination of slowly going further and stopping to let me get used to it, she's soon balls deep in my ass. She lets out a little moan as she reaches the end and I bite my lower lip. Damn this felt pretty good after the pain subsided. She waited a minute or so and asked me if she could continue. I turned my head and nodded. She slowly started fucking me, going back and forth. I grunted lightly every time she smacked into me. it started to feel pretty damn good, her dick going in and out of me, rubbing against my prostate. One of my hands reached down and I started to masturbate my dick, while my girlfriend was fucking my ass. "Mmmm fuck me harder baby," I whispered, pushing my ass against her at the right times. "Alright sugar," she said and I felt her thrusts started to quicken. Her balls were smacking against mine and we were both sweating and moaning.

"Damn you feel so good baby," she says.

"So do you, I love being fucked by your big cock," I manage to reply.

We continue like that for a long time, her fucking me and me jerking my own dick. We both manage to last a little longer, thanks to our recent orgasm. But after a while I can feel my upcoming orgasm again. "I'm getting close," I whisper, barely understandable. Her hand reaches down and joins mine in jerking. She leans down and whispers in my ear, "Cum for me baby. Shoot all of your hot cum out while your new shemale girlfriend is fucking your ass like crazy." Hearing this triggered my orgasm. I clenched my teeth and squeezed my eyes shut. I tensed up for a moment and started cumming. I shot jets of cum onto the sheets of the bed. Cumming like that had worn me out and I let myself relax a bit, but apparently Alyssa wasn't far behind. "Cumming!" she shouted and after a few more hard thrusts, I felt her shoot her hot cum inside me as well. She lowered herself on me, more like softly falling on me. I lowered myself as well, causing my chest and belly to drop in my own puddle of cum, but I didn't care at the moment.

Alyssa lay on top of me, her cock still in my ass, nipples pointing in my back and her heavy breathing in my ear. It took us a few minutes to catch our breath and when we did neither of us moved.

"I love you John," she whispered in my ear.

"Ti amo troppo Alyssa."

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18 Comments
AnonymousAnonymousalmost 8 years ago
Lucky SOB's! lol

I'd give my right arm to have a relationship with a hot transgendered woman!

MdnotapMdnotapover 8 years ago
Truly gifted

I too am in a relationship with a non-op translady and you capture what a romance with a beautiful trans lady can be like perfectly, in fact other than the fact that she's an Italian and mine is an Asian beauty its damn near identical

AnonymousAnonymousover 8 years ago
This story was amazing, as a man in a relationship with a non-op translady I can tell you this is perfect. And actually not that different from my own experience lol please keep this story going. Please

Great and realistic

AnonymousAnonymousalmost 9 years ago
delightful and sensual

loved the range of emotional conversation leading to mutually enjoyable sexual fulfillment. nice pacing!

Arkk89Arkk89about 10 years ago
MOAR!!!!!

....Nuff said. Seriously good story would like to see more.

ChrispeChrispeover 10 years ago
So Erotic

I gave you five stars but you really do need an editor, just for the grammar, not the story line. I hope that you will please continue this erotic piece. Thank you.

leann5redleann5redabout 11 years ago
nice and sexy

from the start it was well writtin. hope you will write more infact im lookng forwoard ot ch 2 of this story ty leann

AnonymousAnonymousabout 11 years ago
her final words

Reading her final words was the icing on a very delicious and well written story. Thank you for sharing.

AnonymousAnonymousabout 11 years ago
Great story

I loved every second of this story. I am so glad that you decided to write it. It's one of the best stories that I have read on here. I hope that you do more chapters to this story.

IwannaTVIwannaTVabout 11 years ago
Excellent read, very well thought out.

I so wish I could be in one of these stories (in real life that is) Your story flowed well and was very enjoyable. I'm not sure if John could handle the anal so easily but he was a trooper in taking it after giving it.

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