[MT] Dating a (trans)woman in grad school. Nobody knew she was trans

Warning: this is long.

I went to grad school for art education.

During my final semester I got to know and date a beautiful girl named Tanya. Though my friends got to know her slightly and my family met her at graduation, none of them – to this day – know that she was actually a trans woman.

I didn’t know either at first. All I knew is that I was smitten with the girl who sat down next to me on the first day of a required liberal arts elective.

Her body was the first thing that got my attention. She was short, maybe 5 foot 3, with a petite frame and tiny little shoulders. But she was also busty, wearing what I later learned was one of several very lacy 32D bras over a fabulous pair of implants.

That first day she wore a tight short sleeved top with a very high collar neck – horizontal black and white stripes – that looked startling with her curves. Down below, she wore big ruffled cargo pants that actually complimented the look in a weird way. Her hair was shoulder length, black with artsy streaks of dark purple.

She had a beautiful face with delicate features, and though she liked makeup, I always thought she looked just as beautiful without any. She wore pitch black lipstick that contrasted magnificently with her pearly white teeth whenever she smiled, and she had ever so slightly longer than average canines which gave her a slight vampire look.

Nothing happened between us on day one but I tried to Break the ice on day two, making an off handed comment about the bad coffee we’d picked up from the student cafe downstairs. She laughed to my great satisfaction. It became clear with conversation that she really liked my sense of humor.

We built a rapport and with a little nudging on my part, one thing led to another, and we started seeing each other outside of class.

Date 1: she touched my ankle with her foot under the table

Date 2: she revealed to me that she was bisexual. This didn’t bother me at all, I actually found it really sexy. We briefly kissed at the end of the night. I started having dreams about being intimate with her.

Date 3: started out great, but then the mood changed. You could tell something else was on her mind and she was anxious. That’s when she finally told me that she was a trans woman.

I didn’t believe her at first and found the whole thing amusing, an insensitive first response which I now regret.

The tone of the conversation became very serious after that.

After I apologized, She softened a little and confirmed that she was into me too, and was excited to continue seeing me, but she needed to lay out her terms for the relationship, and needed my OK for anything to proceed. The fact was, I was intoxicated by her, and if this was who she was, then so be it. I wanted to be with her regardless and see where things went.

Her terms: she needed me to know that she was notinterested in reassignment surgery at all. She was actually afraid of meeting a guy who wanted her to undergo surgery, and she needed my support for her decision “to remain”, so to speak. She wasn’t dysphoric when it came to her equipment – she actually enjoyed her equipment, I later learned.

Part of me wasn’t ready to admit to myself that I was intrigued, but the other part of me – the “life is short” part – won the day.
I told that her yes – absolutely – I am happy with her terms, I’m excited to see where this goes, and I affirmed it later that night when I moved in and kissed her.

She was excited to kiss but she kept it very brief and asked me not to do it with her in public. Not because she had any issues with PDA, but as I found out later, because kissing like that made her hard.

It took a few more dates before we finally had sex, but now that everything was out on the table and she had my blessing, a new side of Tanya broke loose, a side that foreshadowed what she might be like in bed. She loved teasing me, and it gave her great joy to watch me squirm with anticipation. She thought it was funny and adorable, and she liked it because it made her feel powerful.

This became a recurring theme in our sex life. She liked the idea of keeping certain things “off limits”, at least for a little while, because it gave her great pleasure to watch me go crazy.

In those dates leading up to our first sexual encounter, she liked to do this by waiting until I started talking at length about this or that, then she’d just casually start bunching her breasts together with her arms, making her cleavage very long and deep, staring back at me with this devilish smile where she bit her lower lip with those cute vampire teeth. Then when she saw how flustered it was making me, she might stick out her tongue playfully or giggle about it.

This drive me absolutely insane. She knew it too and she loved it.

During this period I was increasingly curious about her equipment, but I made it a point to never ask any questions about it, figuring id get to know it eventually on her terms at and her comfort zone. But at one point she off handedly make one comment that gave me some idea of what I should expect: We were talking about relationships one night and she started talking about a cis-girl who’d she’d dated very briefly during the previous summer.
Tanya had mentioned this girl off handedly a few times before, but now she finally revealed that the relationship ended because of problems in bed: the sex was too difficult and too painful for the other girl. Then she joked about being a self proclaimed expert on lube, and that was the end of that conversation.

The idea that she might have a big cock didn’t phase me too much because of my own size – a pretty thick 7.5″ erection – I’d had one or two similar issues with girls in bed, none total dealbreakers, but i felt a sense of solidarity with Tanya around the issue, even if I didn’t tell her so at the time.

But when I finally got to her place two weeks later and the clothes finally came off, I realized that I couldn’t have been more wrong. The first time I saw her equipment was an adrenaline infused mixture of excitement and fear.

Tanya’s erect penis was a monster. Just a hair over 9 inches long, with a slight upward curve that made it look aggressive, almost like a predator. It was thicker than mine, and got even thicker down at the base where it widened to the girth of a red bull can. It had a big fat circumcised head that was somewhere between the size of a strawberry and a tangerine, almost like a warm velvety ball gag.

The three months we spent sexually active with eachother were a blur of passion and
sweat.

She mentioned that her ex girlfriend first assumed that her cock was 12 inches long, and in certain positions I could totally understand why. Tanya was a small girl and her cock was very long. One night after we’d had a few drinks, she showed me how she was actually able to fuck her own tits.

Some of my favorite things to do with her were actually pretty mild considering the possibilities. Reacharounds were romantic. I’d come up behind her and embrace her from behind, kissing her neck, then without either of us moving I’d take off her pants and begin jerking her off with both hands.

Other times we’d begin on her couch, making out. I’d pull out her cock and begin stroking it slowly with one hand, and then she’d reach out with one of her hands and we’d stroke it together. I always let her grab the top of it, just below the head, and that was her favorite spot and she knew how she liked it. I’d grab somewhere along the bottom half and stroke in sync with her. I thought it was very romantic, and stroking in sync with her made me feel even more connected to her. I loved to watch her face in the moment, she way she clenched her eyes and made a face as though she were crying out, though the moans were soft.

She loved blowjobs more than anything else, and sometimes she even demanded them. It took alot of practice and relaxation to get used to it because even going down on the first four inches (the furthest I could go without gagging), it literally reamed out my entire mouth and rubbed against the tips of my teeth. I was absolutely committed and worked through a period where my jaw would sometimes become sore.

In the end it was worth it as I became an expert at sucking her cock the way she liked, and in those moments I became the dominant one over her. But the size of her cock made it a submissive experience too, given how big it was in my mouth It felt almost as though I was slaving away at it, submitting to it, and submitting to her by extension.

The view was also worth the practice. I loved to gaze up at her while I sucked her cock, though I could only see the bottom of her chin as she always kept her head tilted back, softly moaning up at the ceiling. Her hands was sometimes cradling my head and other times they were cupping her tits, twisting and pulling her nipples with each thumb and forefinger.

The question of her bottoming me was always looming in the background. Maybe that was always my limit. But she didn’t mind going both ways. My favorite position was when she rode me facing forward, as not only could I see her beautiful body but had her cock bouncing around in front of me. Sometimes I’d even lean forward and suck on the head while my cock was buried in her ass.

Her cum was different than mine. A little less cloudy, a little more clear. But with some practice, I learned (forced myself, really) to swallow it all. I loved the idea of drinking Tanya’s essence, it was a natural extension of the way I submitted to her whenever I sucked her cock, like an act of devotion. Sometimes we’d even kiss afterward with the residual cum still on my tongue. Real men swallow, they don’t spit.

As I mentioned before, she was a tease who liked to watch me squirm. And though most everything was out on the table by the time we were sleeping together, she still managed even then to find a way to keep me pent up about *something*:

One night we were switching positions mid-sex. She tumbled across the bed in such a way that her cock briefly swung up near her chin, just a few inches short of her lips. I noticed this and was immediately struck by the idea of whether she could suck herself off. Then I asked her about it.

In the end, she used that anticipation against me, making me squirm and loving every second of it:

One night a week or two later, as we sat on her couch, she began stroking herself and started talking about how much she “loved” to suck her own cock. She described it as “self-lovemaking”, a way to show her body how much she loved and appreciated it. She talked about taking the first few inches into her mouth and sucking it slowly and delicately, never bringing herself too close to orgasm but just becoming lost in the sensation, forgetting about the world and everything else, just “disappearing into endless pleasure”.

But I would never see her do it, she assured me – it was for her eyes only, and it always would be. I don’t know if she was being honest about that stuff, but her goal was to have me under her spell, she certainly had it.

Then, still in front of me, she casually leaned down and kissed the tip of her cock. I was a deer in headlights. She sat up again and looked at me, and giggled with those cute vampire teeth.

Thanks for reading.

Source: reddit.com/r/gonewildstories/comments/57z02h/mt_dating_a_transwoman_in_grad_school_nobody_knew