May I Kiss You?

by Jim Gavin

What’s your gender? Man
How old are you? 56
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: Post-graduate degree (currently pursuing)
What’s your occupation? Advocate
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 30+
How many hookup stories have you here posted before? 1

May I Kiss You?

How long ago did this hookup happen? 8 years

What was your relationship status at the time? Single

How would you best classify this hookup? Sex with an ex

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? Ang is a smart, strong, and sexy woman (though her ex has wrecked her self esteem and she’d not had a relationship for a good few years). Her smile is sparkling and she’s a good figure (shapely legs, pert arse, large breasts, and nice muscle tone). She has a cheeky sense of humor and a lively mind. We’d dated back in the early 90s, but her work took her away. A few years after my divorce, I got back in touch with a Christmas card and was pleasantly surprised when she wrote back and then called. Over the next few months we chatted occasionally, and when she next visited her parents, we arranged to meet for an hour or two when she was free one evening.
There had been no flirting before we met and the evening passed on with conversation and shared coffee. Ang had dressed in her usual style, tight light jeans, and a loose shirt.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? As I said, we chatted for an hour or two on my sofa. She’d told her parents she was with an old school friend to avoid their questions (they had liked me) but had said she’d be home that day.
At around 10:30 she said she had better make a move to go. I told her okay, but asked if I might kiss her before she left (I don’t think I’d planned anything, though I was definitely attracted still). Ang was totally surprised and thought for a second or two before saying “yes.” I leaned in and delivered a gentle lingering kiss. Ang and I had always shared amazing kisses and a couple of times she had cum just through that (a wonderful surprise for both of us back in the day). Our tongues danced together and pretty soon we were breathing heavily, our shirts were untucked and our bodies were pressing close. I had undone her bra too and held and played with her magnificent tits and glide my hands up and down her back uninterrupted. I knelt between her legs to get closer to her and we decided to move to my bedroom once she had called her sister to say she was stopping over at a friend’s.

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? Now in my bedroom I unbuttoned her blue shirt and eased it off her shoulders, still kissing and caressing her pale skin. Next, I took off her white bra so I could suck her shell-pink nipples whilst undoing her jeans. Off came my shirt, and I pushed down the pale denim of her jeans exposing those beautiful legs and white satin knickers.
Ang sat on the edge of the bed so I could free her feet. And that put me between her knees on the bedside rug. I teased my fingertips up and down her long legs. Floating them over her inner thighs. Grazing them over the white fabric that lay tight over her mound. I could just see the shape of her labia through the satin and delighted in knowing the effect my fingernail caress would be having.
Next, I placed my lips to her skin and stated kissing lightly. Moving over her knickers, I added little probes with the tip of my tongue. Ang moaned and sighed with each new sensation I added, and she said my touch was electric. I knelt up at the edge of the bed to kiss her again and ask if she was sure. A breathless “yes” had my permission to take my mouth back between her legs. I removed her knickers and paused to admire her naked body. Erect nipples, curves and muscle, softness and strength. And a furry triangle. Mmmm, I adore soft neat curls on a woman. Ang was very turned on and when that happens her inner lips begin to show. I kissed and licked them lightly to increase the effect. Then, I gently but firmly sucked each one into my mouth reveling in the sensation of Ang’s softness. Her deep sighs told me she was loving my attention.

Next, I licked either side of her hooded clit. All the way to her dripping opening and back. Then, up the middle between her folds. Now swirling around her clit. And sticking it between my lips, into my mouth pressing my face firmly against her. I added two fingers inside. I remembered her wet contours from before. The soft mound just inside and the ribbed place just beyond where Ang loved to be pressed. She was so sweet and wet, and I soon had her cumming hard. She is incredibly multi-orgasmic and each one can last for ages, so I continued to caress her and guide her fully onto my bed. I told her she was beautiful and kissed her again. “I thought this part of my life was over,” she sighed. “No, you are gorgeous and so sexy,” I said as I kissed away her frown. She smiled and spread her legs to me. Her wet cunt, slick with her juices, opened slightly. I placed the tip of my hard cock between her labia and began sliding it over her clitoris. I love this feeling of her slippery folds parting for me, of seeing my length and thickness giving pressure. Ang looked down smiling as we rocked in time. Ang adjusted slightly and the tip of my erection rested at her open cunt. Our eyes met. And we slowly drew together. She took my 7 inches all the way in. She felt amazing: hot and soft and tight and wet. I could feel the rippling of her continuing orgasm as she moaned and held me close. “Don’t stop. I want to cum and cum and cum,” she whispered. I thrust and teased with shallow strokes and pounded, and drifted and she matched each change. She felt my climax approaching and knew I’d withstand at the last moment. I held it as long as possible, melting into each other lost in pleasure. Then, with the first pulse of cumming, I pulled out and sent jet after jet off hot white slippery cum over her belly and tits. There must have been 8 or 10 white stripes over her gorgeous body, and still, I was dripping the last of my semen onto her sandy colored curls. I kissed her and we pressed close in a slippery sexy embrace. Rubbing together covered in my cum, my still hard cock sliding and popping between our bellies. Ang grinned and pushed me onto my back. Her mouth enveloped my erection and she licked and sucked me clean. Then, she mounted me. We fucked for hours more and shared more cum positions than I can recall.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? Ang and I had many more encountered over the next few years until work and more monogamous relationships took over. We are still good friends and who knows…

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Withdrawal

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection

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? 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? No one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

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

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? Reconnecting with Ang, sharing our closeness and making her feel great

What was the WORST thing about this hookup? Nowt

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Nope

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

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

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