by PhilandSoph

Gender: Male
Age: 30
Race/ethnicity: White-irish
Current location: Dublin
Highest education received: College degree (eg., BA, BS)
Occupation: Teacher
Relationship status: Long term non monogamous engagement
Religious affiliation: Atheist
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Straight, but not worried about getting my hands dirty in group sex
How many sexual partners have you had in your life (including oral sex)? 34
How many hookup stories have you here posted before? 3

Filling Nene’s Ass

How long ago did this hookup happen? 6 years ago

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…)? Short fling / 3sum/4sum
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? Nene is a childhood friend of mine and our lodger Dean, a pretty, slender 24 year old with mixed British and Japanese heritage. Despite knowing her a long time we had never had sex and had only made out a handful of times

She was nearly 5’5 with a perfectly even pale-asian complexion, short dark hair and large brown eyes. The breasts were barely an A-cup, but with a surprising perk to them. Under the clothes she was perfectly hairless and lean with a very tidy vagina and anus that almost blended into her skin tone

Dean was my age, slim and around 6’2. He rented the spare bedroom from me and my fiancée. His junk was on the small side and slightly strangely shaped, curving heavily. Dean had fucked Nene a few times when they were experimental teenagers but hadn’t had any contact for nearly a decade at this point

Sophie my fiancée was a little younger, a 5’7 hippie with light brown dreadlocks. her skin was pale and covered in freckles. Her figure was slender, a 32b, flat stomach, long thin legs, perky buttocks but with surprisingly curvy hips. The breasts were spectacularly perky, really maximising what a B-cup can offer. The nipples were a pale pink, medium sized and puffy when soft.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Nene was a girl that really knew what she wanted! Earlier in the week we had been chatting on a social network when she told me that she had recently had a contraceptive coil fitted. Jokingly I said she was welcome to come around and put it through its paces and didn’t really think any more of it.

Friday evening rolls around, Sophie is out having a girlie night and me and Dean are just chilling with some beers and video games when I get a call from Nene saying she was thinking of coming around for a visit. The coil conversation had completely slipped my mind so I thought it was just going to be a night of heavy drinking and shit talking

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? Oral both ways, unprotected vaginal/anal sex, sloppy seconds

Nene initiated things by simply asking for a foot massage, me and Dean taking a foot each, drunkenly getting higher and higher up her leg. Obviously ready to take things a step further Nene asks if she can borrow my laptop for a minute. Here she did something neither of us expected, loading up a sex-toy website and pointing out various things she would like to buy. She particularly focuses on a vibrator with an additional anal penetrating device.

She places the laptop down on the table and just slips her jeans and knickers off in one smooth movement. Me and Dean are sat on either side of her on the sofa, both pretty pleased with the way the evening was going. She picks up a coin from the table, turns to me and asks ‘heads or Tails?’  I reply with ‘heads’ and she replies ‘heads it is!

She kneels on the floor in front of me and begins unzipping my fly as Dean looks on stunned. She looks over and tells him ‘Tails!’ he shyly moves to her rear and starts unbuttoning his own fly. Within a minute Nene is performing surprisingly good deep throat while Dean pumps her pussy doggy style. A couple minutes later Dean grunts, stops thrusting and takes a drink of his beer. Nene asks us to swap ends.

Dean takes a seat on the sofa, lighting a cigarette as Nene begins cleaning his shrinking cock. I position myself behind her, easily sliding into her cum dripping pussy. After a few thrusts I have a brainwave and begin lubing her ass with Deans cum, working it in with my fingers as I fuck her. I pull out of her and smear the last of the cum over the head of my cock and start working it into her anus. Ever the professional Nene pushes back, opening her sphincter for easier access.

After several minutes of pretty fast fucking she looks around at me and asks me to cum in her ass to which I soon oblige. After that we relaxed on the sofa with a bunch more beer and cigarettes. Nene spent the rest of the evening naked, sprawling over us as we talk shit, our greedy hands playing with her body, our greedy tongues licking and sucking her, our greedy fingers working their way into her holes.

Towards midnight Sophie returned home drunk and horny and quickly shed her clothes and joined us on the sofa. Dean had seen her naked quite a few times over the years but had not done more than play with her breasts. I pulled Nene onto my lap for one final fuck before bed, Sophie took a seat in Deans lap and positioned his hands to play with her breasts while she watched me

Not long after midnight I came for the last time and Nene told us she needed to be up early the next day so she was going to head home now

Did you have an orgasm? Did your partner(s)? Nene had a couple orgasms, Dean had two, I had three, Sophie the one

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Nene had a coil fitted, Sophie was on the pill. All of the sex was unprotected and we both came inside her ass and vagina. Dean did not penetrate Sophie, but I still had plenty of him and Nene’s juices on my as we had our bedtime sex

What were your REASONS for having this hookup? Drunken horny young people doing what drunken horny young people do best

Were alcohol or drugs involved? If so, how much? lots of beer

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 never had another session with Dean, but Nene joined me and Sophie fairly regularly over the next few months and was my girlfriend for around six weeks before she met someone else and decided to go for a more conventional relationship

To whom did you talk about the hookup? How did they react? Only the people involved and a couple other casual sex partners

Was this a consensual and/or wanted experience for you? For your partner? Completely consensual

Do you regret this hookup? If so, why? not at all

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? Nene had an amazing body, a good sense of humour and absolutely loved anal

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

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

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