The Ex Files

by Jamie

What’s your gender? Woman
How old are you? 30
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? London
What’s your current relationship status? In a serious relationship (monogamous)
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 1

The Ex Files

How long ago did this hookup happen? 1 month ago

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For more than 3 years

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? T is drop dead gorgeous! He is very tall with an incredibly slim waist that I love to wrap my arms around. He has the perfect body, not too buff but just enough for me to want to sink my teeth in to his pecs.
We dated for a few months in our early twenties but soon after we broke up, we realized the sex was much better! We were both less concerned about being well behaved in order to make a relationship work and as a result we became much more sexually experimental with each other. Over the years we have both been in and out of relationships but when either of us are feeling particularly horny in that way that can only be satisfied by each other, we get in touch. We’ve recently been speaking a lot more and have become quite good friends! He’s been there for me through some difficulties.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We are always looking for a good opportunity where neither of our current partners are around and a few weeks ago the perfect opportunity arose. We planned for him to come over to my place as no one was home all evening. We both instigated it as we were so horny for each other.
I had recently lost a bit of weight and was feeling much more confident about my body. He had previously mentioned that his wife wore some sexy lingerie for him and that made me determined to reclaim my number one spot at the top of his sexual fantasy list. So before he arrived I slipped into a tight black and pink teddy and hid it underneath a knee length nightdress.

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? He knocked on the door and I let him in. As soon as the door was shut his arms were around my waist and mine around his neck whilst we kissed passionately and his hands started to explore my body. We moved in to the front room and he started to stroke my legs, lifting up my nightdress at the same time. My teddy had a halter neck line so he still had no idea I was wearing it, I’m pretty sure he thought they were just regular panties as he was squeezing my ass. He then stood me up facing the wall and bent me over slightly, kissed down the back of my neck and dropped to his knees behind me. He started to kiss up the insides of my thighs and then pulled my panties to the side and ran his tongue across my pussy making my whole body shudder! The feeling of his tongue sliding across my clit drove me crazy and I couldn’t contain myself! He stood up and I pulled at his trousers until he slid them down, his dick was so hard and so big (for some reason I’m always surprised when I see how big he is, my memory tells me how perfect his dick is but my memory doesn’t do it justice) I started sucking him off straight away. I know he loves the way I blow him and hearing him moan softly totally spurs me on. He moved my hair from my face and held on to the back of my head, pushing his dick towards the back of my throat until I started to choke on it. Then I stopped, sat him down on the sofa and straddled him. This time he started to pull my nightdress off and his reaction to what I was wearing was worth a million dollars!! He absolutely loved it and kept telling me how sexy I looked and it just made me feel so good about myself and even hornier so I pulled my panties to the side again (easier than removing the tight teddy) and sat on top of his dick. I swear he fits inside of me like a damn glove! I don’t even need to guide it in, it knows exactly where it’s going and I was already so wet he slid in so easy. That initial moment when I feel how intensely he fills me up is probably my favourite part of the whole experience!! I enter another world entirely and I could see the look on his face and knew it felt just as good for him. I started grinding on his dick which was rubbing against my g spot making me feel like I was going to orgasm in a matter of seconds! Then he grabbed a hold of my legs and lifted me up into the air with his dick still inside me. His strength is a huge turn on, he wasn’t struggling to hold me up in the slightest. He then started to pull and push in and out of me getting harder and faster until he was downright pounding my pussy. I’m pretty sure the neighbours could hear exactly how much I was enjoying myself! We had recently spoken about different options when it comes to him ejaculating, I absolutely love when he creams my pussy but he wanted to try something different. I could tell he was getting closer and he was still holding me in mid air! He suddenly pulled out of me and sprayed his cum all over my teddy. It was ridiculously sexy!

How sexually satisfying was this hookup? Very

Did you have an orgasm? No, but I was 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? In the past we sometimes felt really guilty about our hookups as our respective partners don’t know and would be hurt. However the last few months have been different. We understand each other better and expect less from each other, which is great because we are less likely to get hurt that way.
After our intensely satisfying session we cleaned each other up, got dressed, had a little cuddle and a chat, and he went home. We still talk pretty much every day and neither of us can wait until our next round!
I definitely care about him as we have known each other for 10 years! I know we could never be in a relationship and I’m fine with that. So long as I get to fuck him until it’s too inconvenient for either of us, I’m happy.

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

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

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

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? We cant tell anyone as we are both in monogamous relationships

What was the BEST thing about this hookup? How satisfying it feels when his dick just about fits in to my tight pussy but feels like it belongs there!

What was the WORST thing about this hookup? That he had to leave

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. T introduced me to the world of casual sex and has really opened my eyes. I’d like to discuss this with my partner but am worried he will feel the total opposite and leave!

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

Anything else you want to add about this hookup? This is likely to be one of many stories about me and T…

What do you think about the Casual Sex Project? It’s so great! I love reading about people’s experiences and it has given me a completely different outlook on sex.

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