TL;DR I met a crossdresser through an internet dating site, and our first time was in her SUV.
Carrie (not her real name) and I hit it off right away. She wasn’t that tall, wasn’t that fit, but at the same time wasn’t this weird caricature of women I had seen in the past. She dressed in a way that I liked, her makeup was perfect, her clothing was hot and her look was exactly what I enjoy, and as far as people go, I was elated when she suggested that we park behind this mini mall on that Tuesday afternoon.
I stalked the location on Google Maps before agreeing to meet with her. Sure enough, the back corner of the parking lot is exactly what Carrie said it would be. So I told her that I would show up, she asked me to promise that I would show up, I reiterated that I would be there, and she asked me what I would like her to wear. She sent along a bunch of pretty hot photographs, all clothed, but still the optics/image is what I was looking for, and I picked a look or two that worked for me. We talked about what we might like to enjoy that early afternoon, and she basically said that if everything was cool that she’d be into making out, maybe some mutual oral, and that she loved being topped — if everything was super, super cool on our first date. We also exchanged details about the vehicles we would be driving, and I showed up super early. I wanted to make sure that the current state of the lot matched what was on Google Maps. And it did.
Eventually I hit up the mini mall across the way from this one and watched. Her Suburban SUV parked in the middle of the very back row of the lot and I tried to get a read on how she looked, if it was really her, etc.
I drove slowly to the back left corner of the lot and put my car into park. I gazed over into her Suburban, and she smiled and did this cute, finger-bend wave at me. I got out of my car, and she got out of hers.
We hugged, just like we were old friends and I gave her a quick peck on the cheek. She was dressed in a faux fur coat, but it wasn’t closed in front. The sheen of her tight evening dress, her stockings, and heels were on full display, and she’d even gone to lengths to work on her hair (wig, clearly, but it was a really nice one), makeup, and she smelled amazing. The light breeze on that early fall afternoon made her smell good enough to eat.
She told me that I looked even more handsome in person, and I also admitted that her pictures didn’t do her justice (they didn’t). Then she invited me into the back seat of her SUV. It had tinted windows, so it made sense — given the private nature of what might (and would) take place.
I opened her door for her, and she rewarded me with a peck on the cheek before I closed the door and worked my way to the driver’s side of the SUV. I got into my seat, and we semi faced one another. I’m a tall guy, and she’s pretty tall, at least in heels, so the fact that she pushed both of the front seats forward was extremely helpful.
The first few minutes of our date were… odd. It wasn’t really awkward, but we just kind of looked at each other and smiled. Then we started holding hands, and next thing you know she’s giggling and I’m going in for a kiss. Carrie was quite the kisser. What a tease! Her tongue was warm, her breath was hot, and then our hands started roaming. She told me that she did nothing to suppress her excitement (jock strings, g-strings, v-strings, etc would not be worn), and the front of her dress was showing a little bit of a bump — just like my dress pants were a complete mess and pre-cum was pushing through the cloth in the front of them.
I made the first aggressive move. I pushed her dress up above her stocking tops, and as promised she was totally bare. Her thong, slightly sheer, showed a tiny but visible erection. I pushed her thong aside and fist was wrapped around her. Her own pre-cum was leaking out of her, and after a few strokes, I grabbed a condom (we also negotiated that protection would be worn for any/all activities — aw, shucks!), and rolled it on to her. Then my mouth went to work, and as it milked her tiny shaft, my fingers snaked to an even more private place. As my mouth continued to feel her heat through the latex, I grabbed some lube from the bag of goodies that I had acquired from Walgreens earlier in the morning. I lubed up my middle finger and starting going to town on her pussyass. She didn’t last that much longer, and like a man she tried to fuck my mouth, which kind of pissed me off, but then again I get it. I’m definitely a mouth fucker if I get the chance. I own this 100%. So I get where she was going here, and she came into the condom. She emptied the plastic bag that was filled with condoms and lube, and tossed her discarded condom into it.
I was kind of bummed because I thought that it was going to be over. Maybe after her orgasm subsided we’d just call it a day. But was I wrong. Boy, was I wrong.
She started stripping me aggressively, almost ripping the buttons off my shirt in the process. My pants were pooled around my ankles, and she lapped at the pre-cum that was dripping of my head a couple of times before rolling a condom on to me. Her mouth was hot and tight and her sucking sounds echoed throughout the SUV. From my end of things I didn’t last that long either for the first time. Like she did for herself, she pulled the condom off me and discarded it into the plastic bag when I was done.
We chatted a little bit more, and I figured that she would want to end our first (and maybe only) date there. Again, wrong.
We kissed some more, and she kept kissing, sucking, and nibbling at my nipples, which I totally love and enjoy. I was hard again in no time. Then she asked if I wanted to fuck her. Of course I did. So she rolled another condom on to my cock, thrust off her thong and tossed it on the floor, lubed up her pussy ass, and put on her own condom, which I admit was strange. Then she straddled me and guided me in. It started as a nice and slow fuck where her hips circled around my pelvis before she impaled herself on me time and time again. She used one hand to keep her condom on as she did this. But then as she got hard again, her cock would slap me in the lower belly each time she would plow herself on to me. Was it 10 minutes? 20? 30? If nobody saw that SUV rocking as she bounced on me, they must have been blind. And then it happened. She burst into the condom, and just seeing her second round of cum fill it it was more than I could take, and I shot into my condom, into her, as I told her how hot and sexy she was and how next time I wanted us to consummate things… the right way.
We kissed a little bit and then she climbed off. She put everything back into the plastic bag and asked if I could deal with it. Sure enough I could, and did. After a brief final peck, I grabbed the plastic bag and walked back to my own car. My legs were numb and I thought that I was going to collapse. I found a garbage can at a gas station on the way home and left it there.
We dated a few times after that, including a full-on hotel date that was superb, but I guess that’s a story for another time.
Source: reddit.com/r/gonewildstories/comments/jr6lfg/mt_the_car_date