Impromptu Morning Play

by Tippy

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’s your current relationship status? Engaged/Married (open)
Religious affiliation: Atheist
What’s your sexual orientation? Pansexual
How many sexual partners have you had in your life (including oral sex)? 9
How many hookup stories have you here posted before? 7

Impromptu Morning Play

How long ago did this hookup happen? Last Week

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

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For 1 to 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? I met Cash in a gaming group. He’s about 6’6”, with brown hair, is well groomed, charismatic, bisexual, and a couple of years younger than me, and he is in a long term relationship. We had a previous hook up in an Air Bnb. I wasn’t sure if we’d hook up again, but I was definitely open to it. We have a good functioning friendship with some sexual attraction thrown in. I like him a lot and the way his brain works. I absolutely trust Cash as well.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had arranged to meet up for a walk and a catch up. He arrived a fair bit after I did and I was feeling very tired. We chatted and walked and I wasn’t thinking anything sexual was gonna go down (I was enjoying his company anyway). I was also on my period, which tends not to be my horny time. After a few sympathy yawns, he made the suggestion I take him home with me so he could put me to bed. He’s very cuddly and gives amazing hugs, and the thought of having a doze with him sounded lovely.

Immediately, of course, I’m thinking do I want more than that, and I’m excited to ask myself that question, which means I probably do. I don’t want to push it though, so I just decide to see how it goes and set no expectations. At the same time, I’m bringing a man I’m attracted to into my bed. Stuff is probably going to happen.

We get to mine, chatting normally, and go upstairs into my room. I feel guilty, my husband Saul doesn’t know I’m doing this and I hate telling him afterwards (although it always leads to incredible sex) so I feel very naughty utilising my day this way.

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 stands on one side of the bed and turns around. I start to undress, and it makes me smile that he looks away even though he’s seen me naked. It feels very polite with no pressure, and I remind myself he may not want more than a cuddle. I put on my PJs but leave my pants, as I’ve a pad on and I’m on my period. We both get into the bed, him fully dressed (he took off his jumper) and me in PJs and pants. He puts an arm on top of the pillow and I scooch in to be the little spoon. We are extremely close and I feel blissful and warm. We say very little but just relax in the semi darkness.

I can’t help but be aroused with him this close. We swap around and then I’m spooning him. I know how he loves his nipples touched and my hands wander there and I start to touch and tease them through his t-shirt. Our legs tightly entwine and we start to grind against each other and pull our bodies as close as they can get. I’m now horny as hell, but as much as I want him to finger me again, I’m put off by my period. I flip him onto his back and ride the bulge in his jeans. It’s clear he’s enjoying this by the soft moans and breathes he takes. I’m grinding my clit off the front of his jeans. He reaches under my top and starts to fondle my large breasts and play intensely with my nipples. I’m already dying to orgasm. We kiss intermittently and rub our faces together.

I tell him I’m going to get my vibe and come. He puts forward no protest and I get it from my side table and pop the batteries in. Whilst I do so, he gets his hands into my pants and teases my clit. I want so much just to have him rub me to climax again but I’m too paranoid about it being clean. I lay on my back with my vibrator and I’m so turned on I know this won’t take long as all. He pulls my top up and starts playing with my nipples again, he licks them and flicks them and I come fast and hard. I slide my hand over his groin and feel that his precum has come through his jeans. I’m so turned on by how aroused he is.

He helps me take off his jeans and I start to feel his cock through his pants, then I pull them down and start working his dick with my hand. I can tell he’s enjoying it, moaning a little. I can’t help but think about sucking it, I crave to taste it. I peel back the duvet and roll round onto his chest a bit, watching him whilst I stroke him, touching his balls and perineum. I then decide to go down on him, and he doesn’t stop me. His taste turns me on and I can’t help but start sucking and moving my head up and down. I can fairly easily get most of him in my mouth and I really enjoy the feeling of power.

Then he starts saying softly ‘Oh Tippy’ and moaning. He says my name a few more times. Then he tells me if I keep doing this he’s going to come. I want absolutely nothing more at this point than for him to finish in my mouth so I can swallow it for him. It’s my new trick and I’m very proud of it.
I keep working him and sucking him and putting him in and out of my mouth. I feel him come as a burst of warmth hits the back of my palette and I eagerly gulp it down, trying to suck up any last bits.

I go to kiss him, to see if he’d not be keen or into it. It took some persuasion and made me laugh. I would’ve sucked him dryer if I’d of known he wasn’t fussed though. There’s always a weird satisfaction when you get them to taste their own cum. It was all very satisfying. We cuddled briefly then I had to get going, so we got dressed and resumed general chit chat and walked out together. It was a great morning.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

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? I didn’t enjoy explaining it to my hubby, but in the end we had amazing reclamation sex (as we usually do). I’d only swallowed for the first time recently and I’m glad it was with my hubby first. I’m really surprised by how much I do enjoy it since it’s been something I was so grossed out with for years. I need more practice.

I hope Cash will come out to play again, but I understand there’s probably an expiry on our physical relationship as things stand.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) No penetrative sex happened

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Power / Dominance, Just happened, I don’t know why, just went along with it

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

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

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

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

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

Did your partner(s) consent to this hookup? They didn’t give a clear ‘yes’, but didn’t give a ‘no’

To whom did you talk about the hookup? How did they react? Husband wasn’t thrilled, no one else I told seemed to care one way or the other or that I’m proud of my cum-swallowing abilities!

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

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The cuddly intimacy between us, the natural flow of it, and him saying my name as I got him off.

What was the WORST thing about this hookup? It was in my (martial) bed and I felt guilty about that. Also I wasn’t prepared, wish I wasn’t on my period.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Just a reassurance that I can overcome my mental blocks and try new things.

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

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

What do you think about the Casual Sex Project? Only a few stories left to share unless I go on new adventures. I definitely get a bit of a kick out of sharing my experiences and reading other people’s honest stories.

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