Unexpected First Date Romp

by Daniel

What’s your gender? Man
How old are you? 31
What continent do you live on? Europe
What country and/or city do you live in? UK
What’s your sexual orientation? Heterosexual
How many hookup stories have you here posted before? 5

Unexpected first date romp

How long ago did this hookup happen? 5 years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? Just met that day

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? “Michelle” is about 5 foot 10, long brown hair, usually tied in a bun, with a rocky, casual style. She is not thin, but not fat either, just a little overweight, but still sexy. She wears dark make up with her pale white skin. By looking at her you can see she has a pretty nice ass through her blue jeans and her tight black t-shirt hints she has some nice tits under there. We meet on a dating website, Michelle messages me. I recognise we’ve had a drunken kiss on a previous night out. Her profile picture shows she has a pretty face, and a sexy sparkle in her eye, and nice thick red lips which attracts me. She was early 20s, a few years younger than me. After flirting and exchanging phone numbers we text and finally arrange a date.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I pick her up and drive her to my house. We go for a walk and find out more about each other. On the walk we get on well, and hold hands, and share stories about our families. We get back to my house, and go upstairs to my room as the family is downstairs watching tv. We put on the tv and put a film on, and climb onto the bed to watch it.

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? Laying on the bed side by side we keep talking, but this soon turns to kissing, first without and then with tongues. I’m enjoying myself as my hands roam around her waist and bum through her jeans. Her hands run across my chest and down to my bum. I climb on top of her and continue kissing her down her neck and behind her ear while I can hear her breathing get heavier. Michelle is a nice girl, and I can tell she is not that experienced. I know she’s enjoying herself and she can feel how hard I am against her hip. I start to grope her breasts as I kiss her and then slide her top up. She has no resistance and soon I reach around to unclip her bra. To my joy it reveals two of the roundest firmest big breasts I’ve seen. I take in this beautiful sight before I begin exploring, cupping my hands around them and running across her fairly large nipples. My thumb circles her nipples as my hand grips her tits. She moans as I begin to suck, lick and nibble on her nipples. They taste lovely as I look at her in the eye as I play with her tits. She has her eyes shut though as she quietly lets out a moan and then looks at me. Things have happened fairly quickly, and we are both excited. I decide to take control, and without saying anything I move down the bed, straddling her feet with my head at the top button of her jeans. I look at her and she looks at me as I slowly unbutton her jeans, and then slowly tug them off. It is always one of the most enjoyable moments when any girl lets you slide her jeans off and you know you’re about to have fun and you get to see the panties you’ve been wondering what they look like, and this is no different. Michelle is wearing little black panties. They are not fancy, they are very plain in fact, but it does not quell my excitement as I lower my chest down to the bed. I start to kiss and lick the insides of her thighs and quickly start kissing her little pussy through her panties. I feel the shape of her lips as I run my tongue along the cotton of her panties. I grab her at the hips and tug the panties down, past her knees, and finally off to reveal quite a hairy brunette pussy. I don’t mind though, as I like shaven, unshaven, landing strips – I don’t really care – as long as it’s clean I’d happily eat pussy all day long. I can tell by Michelle’s flushed face she is not used to this, but also can tell by her whimpers she’s ready for more. I position my head between her legs and begin to kiss her gently up and down her pussy a few times before licking from the bottom of her pussy all the way up and over her clit as she moans louder. After doing this a few times I go up to her clit and flick it up and down and then left and right with my tongue. I’m feeling confident as previous girlfriends have always commented and enjoyed (and educated me) in giving a girls clit a good going over. Michelle is now soaking wet as I bury my face deeper in her and her moans get more frequent and louder as nose and mouth are now deep in her as I tongue fuck her hole. She bucks and moans a long exhale as she cums over my face. I lick her juices from around my mouth as I sit up. We look at each other but say nothing. She’s red faced and I’m breathing heavily too. We both know what we want now. I undo my jeans button and slide them down revealing my black boxers, which are hugging around the bulge waiting to get out. Michelle is still flat, almost naked, on her back on the bed, but watches intently as I pull the elastic down beneath my hips and my erect white cock springs out. I watch her eyes light up as she look up and down my shaft and balls which I enjoy. All the eating pussy has got me very hard and ready for more. I reach to a near drawer for a condom and slide it on. Again, without saying anymore I straddle her legs and point the head of my dick at her entrance, before sliding a little in. Michelle is very wet, and so gradually as I lean forward and begin kissing her I’m able to slide right inside her until I have filled her up to my balls. It feels so good, and I begin rolling in and out of her pussy, as my hands search her breasts. Michelle holds onto my ass as I bury my head into the pillow beside her as I use my hips to pound into her harder. Thoughts briefly go to disbelief about how we so quickly got to this point, but neither of us are going to worry about that now. I feel her walls grip around my cock as I continue to slide in and out of her, arching my hips up to find her G spot. I grab onto her thighs and pull her legs wider so I can gain greater access and feel my balls slapping against her bottom. She begins to tense up, and I go harder, before she bucks her hips, puts her hand over her mouth and climaxes around my dick letting out a long, muffled sigh. I barely hold on from this, but I’m ready to cum anyway, so I grab her waist, and bury my head between her neck and her tits and fuck her as hard as I can. Before I shoot my cum inside her, as I feel my balls emptying, and I let out a long moan and finally relax.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

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? There was a slight awkwardness, but we laughed about it and both said that we didn’t expect that. Michelle confessed that she was inexperienced and I was one of the first few men she’d been with. The next time we saw each other the same thing happened except she gave me oral sex. Despite the sex I didn’t want a relationship with her which I think she resented. She wanted then to continue just to hook up but I felt that I didn’t want to lead her on as she was a nice person and it wouldn’t be fair. We fell out of touch.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

Did you consent to this hookup at the time? I gave enthusiastic consent

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

Did your partner get emotionally hurt as a result of this hookup? Somewhat

Do you regret this hookup? A little bit

Why do you regret this hookup? Only because she wanted more and I couldn’t give her that

What was the BEST thing about this hookup? Eating her pussy, and seeing how much I pleased her. Possibly she had never had anyone time that time to go down on her like that before

What was the WORST thing about this hookup? After we had came, the awkwarness

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Sex can be fun, in or out of relationship – although sex outside relationships can lead to more confusion and misunderstandings.

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

All things considered, how NEGATIVE was this experience? A little negative

What do you think about the Casual Sex Project? I really like it, and its very interesting. I enjoy reading the stories, and often wank off to them, and was pretty aroused recalling this experience and writing about it. I enjoy reading the ladies naughty confessions in particular as you don’t often hear their stories as much so its good to read. I prefer the stories that take some time and that are quite erotic. I also prefer the ones with the dirtiest language.

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