My Third Time as a Bottom with a Shemale from the Chat

More than a month had passed since that first time when I accepted my guilty pleasure, that night when, for better or worse, I ended up losing my virginity as a bottom without really planning it. During those weeks I spent my nights browsing the internet at odd hours, watching images and videos of trans girls fucking men, feeding a desire I no longer knew how to silence.

That was how I found a site that was still new, organized into rooms where you could talk to people from many places. I started by entering the gay-themed rooms, writing every so often, chatting with strangers, almost none of them Mexican, by the way. Until I noticed there were rooms created by the users themselves, and among them one for transvestites and transsexuals. I clicked the famous link and went in.

For the first few days I just read. The conversations in the main room, the same questions and answers as always, the usual stuff that back then was still novel. I went in whenever I had some free time, not daring to do more. Until one afternoon a nickname appeared that said “active transvestite.” With the little I knew from my awkward previous debut, I gathered my courage and wrote to her.

—Hi, good afternoon. How are you? —I typed.

—Good afternoon. Fine, and you? —she replied right away.

—Fine, taking the liberty of writing to you because your nickname caught my attention.

—Wow. And why did it catch your attention, if I may ask?

I told her the truth: that I was pretty inexperienced with transvestites and transsexuals, that not long before I had had my first experience with a man, and that I was curious to know more. I asked where she was from and she said Mexico City, near Revolución station. I told her my neighborhood: we were less than an hour away. She asked what I looked like physically and I gave her my height, five foot nine, average build. She told me she was five foot nine and a half, stocky, with fair skin. She introduced herself as Rebeca; I gave her a fake name, because I was using a different nickname from my real one.

Once we got down to business, she was the one who took the initiative. I confessed that I didn’t have much sexual experience, that I had only been with two women and that my first encounter with a man had ended with me on the receiving end.

—And why was that? —she asked.

—I let myself go. By the other person and by my inexperience. He seduced me until he ended up fucking me.

—Hahaha, they took advantage of your innocence —she wrote.

—Maybe, but I’m not complaining. It gave me experience. I got to know a new world.

—And would you like to have more experience?

—Yes, I would.

She suggested we meet the next day at the corner of the avenue that led to the main one, near the subway, and she gave me her phone number. I sent her a text right away so she’d have mine. We chatted a few more minutes and agreed to be punctual at the agreed time and place.

***

The next day I arrived half an hour early. I kept pacing, checking the time, with a mix of nerves and desire that wouldn’t let me stand still. At the appointed hour my cell phone rang: it was her, saying she was nearby already, that she had been delayed by some issues. She asked how I was dressed and I described my black jeans, the gray-and-red T-shirt, the cap, and the white sneakers.

A few minutes later I saw her approaching. Taller than me, not very attractive but not ugly either, stocky, a little on the plump side, wearing a long black skirt and a white blouse with floral trim. Her brown hair fell over her shoulders. She recognized me, came over, and greeted me with a kiss on the cheek that I returned in the same way.

—Follow me —she said—. I know a place where we’ll be able to relax.

We walked a few blocks talking about trivial things, me half a step behind her. We reached the front of a hotel that seemed pretty modest to me, but she assured me it wasn’t so bad, that she had once stayed there for work reasons. We went in, paid for the room at reception, and went up with the key in hand.

As soon as I closed the door, she got behind me and hugged me from behind, her hands on my waist. She brought her face close to my ear.

—I hadn’t gotten a good look at you until now —she murmured—. You’ve got a pretty fat ass. No wonder that person fucked you.

She slid her hands down the front of my pants. She undid my belt, unbuttoned my pants, and told me to take off my sneakers. I bent down to untie them and she took the chance to press herself against me. When I straightened up, still glued to my back, she pulled my pants down to my ankles and took them off completely. Then my T-shirt. I was left in nothing but my boxer briefs in the middle of the room.

She hugged me from behind again and started kissing my neck. Her lips moved slowly upward, her tongue playing behind my ear, and I could feel my skin prickling. Without realizing it, I let out a couple of soft moans. She stayed like that for several minutes, gauging me, until she pulled away, slapped my ass, and pushed me toward the bed.

I sat on the edge. She took off her skirt standing in front of me, moved aside the black lace panties, and pulled out her cock. It must have been about six and a half inches, nicely thick, with a drop of fluid already gleaming on the tip. She brought it close to my face without saying anything. No need: it was crystal clear what came next.

I took it in my hand and started licking it from bottom to top, running my tongue all over the shaft to the head. I took it into my mouth, circled it with my tongue, pulled it out, and went back over the whole thing again. I repeated the motion a couple more times before taking it all the way in and starting to suck it rhythmically.

—You suck it so good —she moaned, with one hand on the back of my neck—. What a pretty little mouth you have.

I kept going until she stopped me. She made me stand up, yanked my boxer briefs down, and left me completely naked in front of her. Then she bent me over the bed, slapped my ass again, and tried to slide a finger into me. My hole resisted the intruder.

Noticing the resistance, she spat, and the saliva fell right between my ass cheeks. She pressed the finger to my entrance and wet it, circling around it, trying to work it in little by little. At one point it broke through and went halfway in. I let out a loud moan. She spat again, pulled the finger out, repeated the ritual, and pushed it back in, this time all the way, holding it still for a moment before starting to twist it inside me.

My moans became more constant. I was enjoying it, I couldn’t deny it. And then I felt a second finger going in. It started sliding in and out faster, spitting every so often to keep it slippery, and my moans rose in intensity. Suddenly she stopped moving and pulled her fingers out.

—Do you want me to put it in you already? —she asked.

—Yes —I managed to answer between gasps.

With some force she threw me onto the bed, turned me over, and put my legs over her shoulders. I felt the head of her cock resting at my entrance, pressing to force its way in.

She started to push in slowly but without stopping. I could feel her working her way inside me, inch by inch, never pausing. I wanted to move a little, I brought my hands to her hips to stop her, but she grabbed my wrists and held me still, with my legs over her shoulders and no way to escape her thrusting. She kept going until her hips slammed against mine.

—Ah… you squeeze so good —she panted.

I could feel her occupying me completely. She started to pull out very slowly, until she came all the way out.

—Your open hole looks so good —she said, and rammed back into me all the way to the hilt.

From there the pace increased. She had me pinned down, legs up, arms held by her hands, with not the slightest chance of moving. Under her power, I moaned every time she went in and out, and she moaned with me on every thrust. She sped up, gripped my wrists harder, slammed into me more eagerly. And then, in one moment, she drove in all the way, moaned hard, and I felt something hot spilling inside me. She let go of my hands, lowered my legs, and moved away.

When I felt free, I reached back with my hand. I could feel it stretched, open, and something hot and thick leaking out. She had come inside me.

She lay down next to me, facing me, and hugged me.

—What did you think? —she asked.

—I loved it —I answered—. Did you come inside?

—Yes. You were so good I couldn’t hold back.

—It’s the first time someone’s done that to me.

She flashed a huge smile and kissed me. We stayed like that for a few minutes, kissing, until she ran a hand over my waist and pulled me firmly toward her. She started massaging my ass without stopping the kissing and, little by little, got me lying face down.

***

She got on top of me and positioned her cock at my entrance. This time it went in without resistance, straight to the bottom. She started fucking me in and out, increasing the intensity, her hands on my arms so I couldn’t move.

—This little ass is all mine —she said between moans—. You’re so fucking good.

She fucked me like that for several minutes. She pulled all the way out and then slammed back in with one thrust, ripping stronger moans from me each time. Then she stopped, stood up, and forced me to stand too.

—Now it’s going to be your first time trying something different.

She made me kneel and held her cock in front of my face. I wanted to take it into my mouth, but with a gesture of her hand she stopped me. She started jerking off in front of me, slowly at first, picking up pace along with her moans.

—Ready or not, here I come. Take it —she said.

She let out a stream of semen that splashed straight onto my face. I barely had time to close my eyes. I felt the hot stuff on my cheeks and lips as the shots kept coming. When I opened my eyes I stood up and went to the mirror: she had shot a good amount. She moved in behind me, laughing.

—What did you think of your first experience like this?

I didn’t know what to answer. She handed me some paper and I started cleaning myself up.

Once I had all the cum off my face, I went back to the bed, where she was waiting for me, seated. We talked for a while about how I had felt.

—I did like it —I admitted—. It’s something completely strange, but it felt good. Even more so seeing that you were satisfied.

She pulled me toward her and kissed me.

—It’s time to go home —she said.

We started getting dressed. Before leaving the room, she gave me another kiss and one last slap on the ass, telling me she would be looking forward to the next time I wanted to see her. We left the hotel and walked to the place where we had met. Each of us headed off to our own destination, with the hope, of course, of meeting again.