First Date Surprise

by CardsForChloe

What’s your gender? Trans woman
How old are you? 32
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? England
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Human Resources
What’s your current relationship status? Single
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Bisexual
Any other term(s) that describe your sexuality or sexual identity? Transgender, Experimenting, Exploring, Open-Minded
How many sexual partners have you had in your life (including oral sex)? Six
How many hookup stories have you here posted before? None

First Date Surprise

How long ago did this hookup happen? Two months ago

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than a week

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? The man in question was quite handsome, he had a lovely smile, nice well-done hair, he certainly appeared to have the body of someone who worked out but he was still quite slim and athletic.

We hadn’t met in person before but had been chatting on Tinder for about a week, most nights about our days and a bit of friendly flirting as well. After a few nights of chatting he asking me out for a drink at a local bar which I said yes to.

I was quite nervous about meeting him at first, given it was a first-date but he did seem sweet when we chatted and I did find him physically quite attractive as well as his personality, so I was excited to be meeting him in-person as well.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The date started at a local bar and after a few drinks, he asked me back to his for a movie. After a few drinks I was a little drunk at the time but was enjoying his company so thought it might be nice to go back to his and spend some more time with him.

The actual hook-up began at his, pretty much not long after getting inside the door. Our chat had got more and more flirty on the ride there and I could tell he was getting quite turned on the closer we got back to his house. We walked in the door and he grabbed me from behind, putting his hands on my bum and pulling me closer into his body, gently kissing my neck and lips, at which point I could feel his erection making it’s presence known down there in his pants.

There wasn’t any planning involved, it was more of a spontaneous moment and he very much was the leader in all of this, I think he knew what he was after that evening.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? During the hookup, we had a bit of fun doing a few things. As we were kissing, I could feel his erection in his pants and after some light stroking over the top, he slowly pulled his pants down before letting me go down on him and give him a blowjob. While I was sucking on him he would regularly reach for my boobs and hold them, or grab my bum, at times fingering me in the process. We moved to the couch and he let me continue sucking him. After what was an enjoyable time going down on him, I could feel him tense up and start to moan a little louder, so I continued to move my mouth up and down on him, until he pushed me away, somewhat puzzled looking back at him, I felt his grip on me change and then very suddenly could feel his ejaculate shooting out, mostly across my face and chest but also in my mouth. I sort of just looked dumbfounded at the time, he’d made quite the mess and in all the rushed fun I’d not quite managed to get fully undressed hence I now had quite a bit to clean up.

During the fun, mostly me giving head, I felt great and so empowered, I could feel his every shift, the tensing in his body, the waves of pleasure I was able to give and then being the reason he was able to ejaculate so much was the ultimate compliment, although endlessly messy. He was very into it through the whole process, he obviously enjoyed getting head and I enjoyed him playing with my body while I did it, touching my chest and bum throughout. We didn’t quite make love but I would consider him an OK lover, he left me to it down there and was responsive to what I was doing, plus he obviously managed to cum.

We talked a little afterwards and he mentioned it had been a while since any woman had made him cum just only from head, which put a little smile on my face and I had to confess that I wasn’t expecting him to finish on me but rather in my mouth, but we were able to laugh about it. It ended with me having some time to clean myself up while he ordered me a taxi home, although feeling a little embarrassed on my part entering the cab knowing what those marks on my dress had been from.

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, not even close

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? After the hookup, I had a bit of a hangover the next day but was also feeling in good spirits about it all. To be honest, my dress was somewhat ruined, I realized it has ripped a little during the night and he’d made a mess of it when he finished. I did wonder just how I looked getting into that cab.

We’ve since had a few flirty chats via text and talked about that evening but we’ve not met up again for one reason or another. I do still find him attractive and would consider perhaps going further with him another time but not sure he is relationship material.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal, No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Intoxication, To feel more desirable, To feel more confident, Just happened, I don’t know why, just went along with it

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? I brought it up with a few girlfriends and views ranged from, ‘you go girl’, ‘you little minx’ and so on to just be careful and make sure you don’t put yourself in dangerous situations. I never felt in danger throughout the night and felt like I could stop at any point but I didn’t want to. I’m far from the expert but I’ve even had one girlfriend ask me about my blowjob technique so she can try on her boyfriend.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I really enjoyed being able to give someone that pleasure, to see their reaction, and secretly, while it came as a surprise, I actually found it quite a turn on when he took control and finished on me.

What was the WORST thing about this hookup? Dealing with the mess afterward wasn’t ideal. Given he had finished on me, my makeup was ruined and he managed to leave quite the lasting marks on my dress at the time. For cleanliness, I would have preferred he finished in my mouth but there was something quite hot about just laying there a little dumbfounded with his cum everywhere.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It’s given me the confidence to try new things, perhaps explore a little more and not be so hung up on the repercussions of sleeping with someone on the first date if you are both happy to explore.

It’s also reaffirmed in my mind that I do enjoy giving head and quite enjoy the visual sight of the male orgasm, plus I now have a technique that works wonders.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? I still think about that night at times and have caught myself fantasizing about it once or twice since. I still have that dress too and have worn it again once or twice, as it always tends to get me into trouble.

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I believe that if casual sex is important to someone, they should be able to do it without feeling any shame or remorse, be they male, female, transgender, etc. I wish I had been more open to that side of things when I was younger but am having fun exploring it now.

More widely I wish society would accept that casual sex happens, that it’s women, men, mothers, fathers, sisters, brothers, etc. who are all taking part and as long as they are having fun and hurting no-one, then they should be respected for doing something that is both natural and enjoyable.

What do you think about the Casual Sex Project? I think this is a great resource and opportunity for people to speak openly and candidly about their sex life, something that seems to be quite taboo in society, especially for women and transgender individuals. If it helps just one person to have more respect for themselves and be confident in who they are then it’s a great tool for the community.

You have a hookup story to share? Submit it here!