A Reprise

by I should regret this

Gender: Male
Age: 30
Race/ethnicity: White – British
Current location: England
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Lecturer
Relationship status: Single
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 4
How many hookup stories have you here posted before? 4

A Reprise

How long ago did this hookup happen? Yesterday

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Meeting up with a former fling.

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? E, as described in previous stories, has aged far better than me (I’m almost bald compared to last time we met). She’s still stunning, long dark hair, cheeky eyes, perfect pale skin. I was apprehensive about meeting; it’s been a long time and we only really got properly back in contact thanks to this website and my posts. It felt crazy to be going back to a fling that had been emotionally difficult to end and was so far in the past – but it also felt incredible.I just wanted her to be exactly as she had been during our last dirty weekend.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? In reality the hook up began here, on this website. I had posted a couple of stories, chanced my arm by messaging E about them and it had got us talking. Lots of old feelings came up and we got very flirty. She suggested that if I was ever in town we should ‘write another chapter’. I tried to act cool, but pretty soon was finding any old excuse to travel up there. She must have known my being in town so soon after was one hell of a coincidence, but she didn’t let on. I told her I’d be around for a couple of days early in July, she made sure she’d be free, and started the familiar old routine of texting me dirty ideas. She also announced that she had ‘a couple of surprises for me’.

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? I’d booked a hotel for my stay, and we’d arranged to meet in the hotel bar. I was walked in and spotted her hair a mile off, she still looked pretty much identical from behind in a simple little black dress. I walked over and immediately saw her first surprise. She’s pregnant. Fairly prominently. I must have looked shocked because she grinned, whispered surprise, and leant in to kiss me. We chatted some, she apologised for not telling me she was pregnant (she hadn’t wanted to put me off), and once she’d drank an orange juice and I’d finished a glass of red she suggested we go up stairs.

In the room she kicked off her little heels sat on the bed and sighed – before joking that I’d better appreciate them because pregnancy weight and heels didn’t match. I leant down to kiss her sore feet, then ankles, calves, she spread her legs more and her dress rode up. She had no panties on. She grinned that same devilish look I remembered and lay back on the bed whilst I kissed up her thighs, pushing the dress up with my head before licking her pussy. Between my fingers, tongue, and lips I made her writhe on the bed and watched her cum. I stopped and admired her, naked from about mid-bump to her toes, slightly sweaty post orgasm, just perfection.

I started to strip and she sat up to stop me. Then she unbuttoned my shirt for herself and kissed my chest and sucked my nipples. She slipped a hand into my trousers and felt my erection. Then she looked a touch nervous and whispered in my ear that she hadn’t had sex since she got pregnant (her husband found it weird) and to be gentle. It was sweet that this sexually liberated and confident woman was nervous, it was also funny that in an empty room she needed to whisper. I took her hand out of my pants and we just stood, holding each other and kissing, I lifted her dress over her head, removed her bra and admired this utter goddess. Her baby bump protruding, slightly more swollen breasts than I remembered, I lay her down and kissed her body, her boobs, her bump. I stripped and she suggested I take her from behind (it was more practical given the belly). She reached between her legs, took me and put me inside her. She felt amazing, we fucked for a long time, she had a very vocal orgasm and then I came inside her. We lay down, spooned, and she told me how much she’d needed that, how good it was to have a familiar dick in her, how she’d missed me.

Did you have an orgasm? Did your partner(s)? Yes, she had two.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Given she was already pregnant I wasn’t too worried about that.

What were your REASONS for having this hookup? Lust, memories, and a little bit more lust. She had long been a figure of my fantasies since our first hook ups, it turned out she was having a dry spell, so we helped each other out.

Were alcohol or drugs involved? If so, how much? I had a beer, she had nothing.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? We lay on the bed naked and spooning, and chatted about how life was, how her marriage was going, the baby, why her husband wouldn’t sleep with her, and then she sat up and announced her second ‘surprise’. She had told her husband about our fling years ago. When I got in touch she had shown him this site. He liked what he saw and had agreed to her meeting me for sex. He found the idea of sex with a pregnant woman odd, but liked the idea of her sleeping with me. I felt a bit betrayed and used, but, given she was massaging my penis whilst she told me this, couldn’t help but be aroused. She said sorry for the deception and then performed oral sex on me. She stayed the night, and we had more sex throughout and again the following morning. Her husband came to collect her as I was checking out. Bizarrely, he shook my hand, told me E hadn’t been so excited about anything in ages and asked if I could make any more trips to see them before the baby’s born. I know I’m thinking with my dick but the three of us are already planning my next visit.

To whom did you talk about the hookup? How did they react? Oddly, her husband. He likes the idea and is actively pursuing the idea of further hookups.

Was this a consensual and/or wanted experience for you? For your partner? Yes, it turns out also consensual for her husband which I hadn’t known until after we had sex.

Do you regret this hookup? If so, why? I regret not knowing the full story before hand. However, knowing that the ‘relationship’ will consist of me and E making each other cum with a fairly distinct end-date (the birth) and no prospect of a long term thing is actually quite liberating.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best on an emotional level was getting to be with someone who has pre-occupied my mind for so long. Sexually, the prospect of a second fling with E – fully sanctioned by her husband – is thrilling.

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

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

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