My friend Benny (M41) and his new friend Elena (T30’s)

This is something that happened to my friend. He’s not much of a writer, but he really wanted to share:

I finally moved to a decent apartment building. Recently my life took a turn for the worse, after my divorce, and finally I managed to get out of a lease on a rundown house in the middle of nowheresville, New Jersey. Then a few months in the slums of a nearby city, and finally from there to a building with a doorman, and nice people who chat up the neighbors, including me.

When I went out to work, I would often share the elevator with my almost next-door neighbor, Elena. An attractive girl with an unusual voice, in her early 30’s, a little younger than me. We’d make causal small talk for almost every weekday, and I took a liking to her without really knowing her well.

I’m straight, even a bit of a macho I was told, and my previous encounters with transgenders were unpleasant. I used to hang out at this dive bar. The beer and hard liquor were good, the crowd was to my liking, and the main reason it was considered a dive bar was the surrounding area. A few times, when leaving, a transgender or a transvestite would hit on me. Hairy, smelly, high (and not in a good way) and not at all typical, so I found out, much later. At the time, it really soured my opinion of trans girls. So I had no reason to think Elena was one.

One day she asked me to hang a few new shelves she got at a famous DIY chain-store. The next day, she found out her washing machine was leaking. She asked me over again, and luckily it was something I knew how to fix. The next day I got the part that needed replacing, and did the work. She wanted to pay for both favors, and I refused. I only had her reimburse me for the part. She offered a dinner instead, and of course I agreed.

Elena made dinner the next day, and we shared a great meal with some wine. She was dressed the way she went to work. A modest blouse, a strict bra under it, pants, and no shoes. Elena suggested a movie after dinner, and we sat down on the couch. Before we started watching, she changed into something less comfortable, revealing, and high heels that made her taller than me (I’m 6’1). We watched the movie, but I sneaked a few peeks at Elena. Long and full legs, barely an inch covered by an apparent night gown, short tights under it in matching skin tone, big enhanced tits with only one layer of the same nighty covering them, soft pale face with long black hair and blue eyes. Nice hands with long fingers.

One of her hands made it’s way to my crotch. My jeans were tight, so Elena simply unzipped them and took the jeans down and my underpants to, leaving them around my ankles. And she started licking my balls, saying nothing. She moved onto my hard dick and surprised me by easily fitting it in her mouth. She used her free hand to masturbate, and the way she did it seemed strange. Like I would, myself, not like a girl would. She got up back to a sitting position and led my hand to her crotch.

That’s when I saw it. A big member with a pink head. Cut, almost as big as mine. I was speechless. Her height and voice made more sense. I wanted to scream and run. But didn’t. I grabbed her cock, neat and pretty, all cute, not as intimidating as a dick would be to a straight guy. But still, so strange. I froze for a few seconds. She lead my head towards her penis and I obliged, trying fitting it in my mouth. Some fit, not a lot. I sucked as best I could, and she smiled, liking it. Apparently I did good. Five minutes into my attempt at a blowjob she released in my mouth. For the first time since we started, she spoke, to apologize. It wasn’t bad though. The sensation was liberating more than anything else, and she tasted good. I said it was ok, and Elena led me to the bedroom.

In there she leapt on the bed, removed her nighty, stood on all fours with her heels still on, and put some lube in her hole. She had me put some on my tip. I stood behind her, and first grabbed her tits. An attempt at some normalcy. I played with her tits in an awkward pose, and they felt nice. My dick was pressed against her hole, and she moved her ass to remind me.

I entered, pretty hard. She wasn’t as tight as my ex, and the lube helped of course. My ex never wanted lube (and she loved anal). The sex was smoother, and her ass was amazing. Not skinny, shapely. I thrusted and she moaned, in pleasure. Not 15 minutes ago she came, and she was semi erect. I kept fucking, and a few minutes into it, a small stream of semen came from her dick. And another two. I loved looking at it happen, and I came inside Elena pretty soon after that. As I got out, some of my cum spilled on the sheets, just like hers did, but from her ass. We lied down on our backs, and I played with her tits some more. She played with my ass, probably hinting at her future plans. I was intrigued, to be honest.

I dressed wanted to get dressed, but Elena suggested a mutual shower. We went to her bathroom and took a long shower, making out under the water. Our dicks hard again, pressing against each other’s body. Elena sucked me off in the shower, and swallowed the small load. She escorted me to the door naked, and asked me to come by for beers tomorrow. I said yes.

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