Getting sucked off by a crossdressing teacher in my car [MT] [M30, T35]

So, let me describe Nikki. She is a thirty-something crossdresser – about 6 feet tall, slim, smooth and with quite a feminine face. She wears her hair fairly short, but it can be teased into a girly style and on both occasions we have met she has used a hairband to achieve that look. Nikki is a drama teacher and is just as confident as an actor-type would seem, but when it comes to sex she is shy as they come.

I first met Nikki not long before Craigslist casual encounters closed down, I think around 18 months ago. I had replied to her ad, and we arranged to meet for some light fun in a car park about 15 minutes from my house. That first time, Nikki was wearing jeans and a t-shirt, but underneath she showed off her sexy white lingerie, with mismatching black stockings. Nothing sexual happened on that first meet, but we sat and chatted for about an hour, mainly about Nikki’s gender dysphoria and her wish that she had transitioned as a teen. Nikki was somewhat sexually experienced with women, having been married for 5 years in her 20s, but following the breakdown of her marriage, the urge to crossdress and the desire to fuck men returned with a vengeance.

Nikki was a virgin when I met her on the first occasion, having never even met up with a man in any way that could be considered of sexual intent before that evening. I enjoyed the chat, but despite Nikki having showed up I honestly thought she was a going to ghost me. Around Halloween last year I got an email from Nikki having heard nothing since the last time we’d met at least 6 months prior. The subject line of the email was, “the urge has returned lol”. We arranged to meet in the same car park.

When Nikki got into my car, she was looking really cute. The whole look was very androgynous. Tight grey jeans, paired with a salmon polo neck top. We sat and talked for a while about how she had been very nervous at the previous meet, but that she had repeatedly jerked off thinking about it. She loved that she had shared with another person her lingerie wearing and fantasised about making love to me. I asked if she was wearing lingerie tonight, to which she began unbuttoning her jeans. Underneath, she was wearing sheer black tights, with a hint of satin black panties visible through the nylon. It was evident that her cock was both small, and very hard. The front of the panties were tented upwards, but the restrictiveness of the tights and panties was causing her cock to struggle to free itself. Despite its small size, it was clearly under some pressure.

I reached across and gently put my hand at the top of her thigh. I caressed, very tentatively the soft material, feeling out her reaction to my touch. When I sensed that she was at ease, I slowly worked my way towards her cock, periodically tepidly touching her crotch. I squeezed her small dick, feeling its hardness. I asked her to pull down her tights. Breathing heavier, she pulled them down to mid-thigh. I began more aggressively jerking her cock through the satin material, before eventually pulling the panties to the side and exposing her whole length. Her cock was indeed very small. It was shaved, with a length of only around 4 inches and not much in the way of girth. As I retracted her quite brown foreskin, I could see a dribble of pre-cum on the tip. She had already explained to me that for years she has been into self-facials and eating her own cum, and knowing that turn-on I put the pre-cum on my index finger and raised it to her mouth. She licked it off and moaned.

At this point I guided her hand across to my own crotch. I noted that she was clearly breathing very heavily and her hand was shaking. I moved her hand over my cock, and allowed her to caress it through my jeans. I was rock solid as well, and she knew it. I unbuttoned my jeans, and pulled them down slightly, also pulling out my cock from my boxers. Nikki seemed slightly taken aback by the size – while I am not huge, my cock was both significantly longer and thicker than her own. I asked her if she was ok, receiving only a very meek “yes” in reply. I guided her hand around my shaft, and began to jerk myself using her hand. Once she was taking over wanking me herself, I went to return my own hand to jerk her, but I noticed that she was using her left hand to stroke herself, and her right hand to stroke me. She had her eyes closed, so I began rubbing my hand up and down her thigh.

“Good girl,” I said. “This is what you’ve wanted, isn’t it?” Nikki moaned in response, shuddering slightly. “Feel the size of my cock. That’s what you want. You need it, don’t you?” “Oh yes.” She slowed her stroking of my cock, and intensified wanking herself. I could tell she was close to cumming based on her heavy breathing. “Stroke your clit, slut.” “Shoot your cum in your panties.” I said, “you’re wanking a man off, this is what you’ve needed.” With that, Nikki grunted and moaned repeatedly. Her breathing remained heavy. This went on for some time, until she gripped my cock tight in her hand and let out a guttural moan. Her cum shot about a foot up, covering her top, with several smaller blasts covering her navel area. When she was done, I scooped up some of her cum and fed it to her. She was clearly satisfied, but there was no respite. “Stroke me,” I said, inviting her to resume pleasuring my dick.

Now, with her own needs satisfied, Nikki took up stroking my cock more quickly. She had lovely slender fingers, and a grip that was just right. She teased the tip of my cock by gently running my foreskin up and down over it. She was doing well. What happened next was quite surprising – Nikki lent over across the centre console and took the tip of my dick into her mouth. She started licking voraciously around the tip while stroking me with her hand. I moved my left hand and slipped it under her ass and began massaging around her hole with my fingers. Above her panties, but enough that I could hear her moaning as she licked my cock.

This continued, with Nikki becoming a bit more adventurous. She was putting more of my cock into her mouth, and working her lips up and down my shaft. Anyone into blowjobs will know that hitting the back of the mouth feels fantastic, particularly if your partner gags, and Nikki was gagging with my cock in her mouth. It felt fantastic. Knowing I was close, I said to Nikki, “are you going to swallow my cum?” “Umhm.” “You want to go home with a man’s load in your belly?” “Mmm.”

I took over stroking my cock with my right hand, letting Nikki continue licking around my tip. I had her lick up and down my frenulum as I jerked myself off into her mouth. I was soaking up the view, in the darkened cabin with fading light outside, I could make out across the car the nylon legs of this sexy crossdresser, while perverse thoughts filled my head. I imagined what her students would think if they knew their ostensibly male drama teacher dressed as a woman and sucked off a virtual stranger. It became too much to handle, and I began to groan as I could feel my cum make its way from my balls towards the point of no return. “Get ready,” I said, moaning. I held back for as long as I could, feeling the hyper-sensitive tip of my cock with Nikki’s tongue swirling around it. Within a few seconds I couldn’t hold any longer, and I released, blasting the inside of Nikki’s mouth with two very powerful streams of cum. Two or three further ropes filled her mouth, and she pulled up with the remainder of my load dribbling out onto my hand. “Swallow it,” I said. Nikki looked up at me, as I continued to stroke out the remaining pleasure of my orgasm and swallowed. She returned her mouth to my cock and mopped up the rest of my cum with her tongue, but I had to stop her due to over-sensitivity. To say I was spent was an understatement.

Nikki was a hive of emotion. She’d been wanked by a man, she’d given a handjob, she’d take a cock in her mouth and she’d swallowed another man’s cum. Over the next 30 minutes we chatted about the experience, and it turned out it was slightly bittersweet for Nikki. It was clear that finally experiencing being a woman had reinforced a notion that she had expressed to me on our last meet that she should have transitioned as a teen. It was a different time in the 1990s, and she was clear that if she was a teen today she would not hesitate to transition. I understood her position that transitioning older is a more difficult thing. A passable trans woman can live incognito. Clearly though, Nikki had enjoyed the experience, and we arranged to meet again, somewhere other than in the car.

A couple of days later I messaged Nikki on Kik, and then later sent her an email with no reply. I hadn’t intended to share this story – it’s a bit more tame than what I usually like to share. However, Nikki and I met up last Sunday in a hotel and I fucked her several times. That is part two, but for now, enjoy the precursor.

Source: reddit.com/r/gonewildstories/comments/bjsoia/getting_sucked_off_by_a_crossdressing_teacher_in