Cheating On Holiday With a Boyfriend

by Wendy

What’s your gender? Woman
How old are you? 46
What’s your race/ethnicity? Black
What continent do you live on? Europe
What country and/or city do you live in? England, Chelmsford
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Buyer for a supermarket
What’s your current relationship status? Dating casually
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Bisexual
How many sexual partners have you had in your life (including oral sex)? 60-70
How many hookup stories have you here posted before? 2

Cheating On Holiday With a Boyfriend

How long ago did this hookup happen? 20 years ago

What was your relationship status at the time? Dating casually

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

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’d been going out with Mike for about 5 months when I realised he was ok but the relationship was going nowhere, I needed to dump him but we had already booked a holiday to Spain where his parents had a holiday villa so it was just a matter of booking flights, Mike was pretty average in every way and I only started seeing him cos his parents had bought him the bar where we used to start our evenings and free drinks were a big bonus.
We got to Spain and went to the villa which he described as ok but I would describe as a palace, it had 6 bedrooms a big pool, gym, Jacuzzi, steam room, sauna and overlooked the med with a path down to a private beach for the residents who owned the villas so I looked forward to two weeks of pampering and sunning myself.
On the second day Mike said he had to go into town to sort out something for his parents and I could go with him or wait, I decided to stay and go down to the beach so I got a towel sun lotion and my iPod and went and sat on a lounger, looking around there were a few people on the beach most of the women were topless so I took my top off and started oiling myself, having done my front I started a vain attempt to do my back when a voice behind said “need any help with that” I turned to see a very handsome guy with a lovely smile on his face aged about 40 (I was 20 at the time) dressed in white cotton trousers and polo neck t-shirt, he had dark hair and the bluest eyes I had ever seen that seemed to smile, I smiled back and said “yes please I suppose I look an idiot trying to do it myself” he said it did look a bit silly but it made him laugh, I passed him the bottle and turned my back to him then felt his hands on my back as he massaged in the oil, his hands were strong and confident and it felt more like a massage than help but I wasn’t complaining and I closed my eyes and enjoyed the sensation after what seemed like not enough time he passed me the bottle and asked if he could join me on the next lounger I said sure so he took of his top showing a nicely toned chest and stomach and his trousers which were hiding a great pair of legs (girls like nice legs as well guys) and laid on the lounger next to me, we got talking and I found out his name was Tony and he had retired to the villa next door I said he was a bit young to retire and nearly fell off the lounger when he said he was 53 and had sold his businesses to live the good life for the rest of his life which impressed me a lot, it was getting hot so he suggested a swim in the sea so we waded in and started swimming a bit, it was at this point I decided I liked him and wanted to fuck him.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I swam under the water and came up coughing he swam over to me and put his arm around me and lifted me out the water a little bit and gently patted my back. I could feel his hand under my boob and enjoyed the feeling I held onto him and stopped the pretend coughing, but never let go I turned to him and curled my legs around his waist and my arms around his neck he said “you sure you’re ok” so with my best shy school girl look I looked into his eyes and said “I am now”, the urge to kiss him was massive but I resisted he smiled and said “that’s a shame I thought you might need the kiss of life”, I said I needed a kiss but not of life and he said we could go back to his villa to see what kind of kiss I needed I looked at the beach and said race you back, he was already at the sun lounger before I’d got out the water and had picked up our things he said he’d go first and leave his gate open for me so I waited a couple of minutes and followed, his villa was a bit smaller than Mike’s but still nice as I walked through the patio doors he was behind the bar he smiled at me which was enough to make me wet and said “drink?”, I said “white wine please” as I sat on a stool, he poured the drinks and came round and passed me the glass I wrapped my legs round his waist and said thanks he said “you don’t hang around do you”, no I said I didn’t come here to admire your villa he put his drink on the bar and moved forward to kiss me he was a great kisser and ran his fingers through the back of my hair as his other hand pulled me to him and caressed my back. I hadn’t been this aroused for a long time and I knew he could feel my nipples on his chest, he untied my bikini top and undid the clasp letting it fall to the floor and caressed my left boob as he kissed and licked the nipple of my other, I moaned with desire and pulled him closer loving every second he lifted me off the stool and carried me over to the pool table and I laid back with my legs open he pulled my bikini bottoms to one side and kneeling started to kiss and lick my pussy every time he licked my clit I moaned and pulled his head into me, I came twice before he came up and kissed me again so now it was my turn I pulled his trunks down while still kissing and started to caress his cock til it was nice and hard turning him round I pushed him back onto the pool table looking down I could see his nice hard straight cock and lowered my head to take him in my mouth his cock was about 7 inches and I managed to get all of it down my throat and stick my tongue out and lick his balls as he moaned, I really went to town licking up and down his shaft while caressing his balls and got his cock nice and wet so I could wrap my boobs round it and give him a tit wank lowering my head so I could take his cock in my mouth as it pushed between them, I looked him in the eyes and he just said “your fucking great at that” I know I said as I took him all the way again, I was wondering where the bedroom was for some more fun when he suddenly said i’m cumming I thought shit not already as I put the head of his cock into my mouth and wanked his shaft til he came in long spurts into my mouth which I swallowed, he looked up and pointed to a door and said with a smile the bathrooms there I smiled back and said what do I need that for, he said wow I love a girl who swallows sorry I didn’t last long but your very good at that, he got up and taking my hand led me to a door and into a bedroom with a huge bed I got on and he followed pushing me back and spreading my legs wide he began to lick my pussy again til I came then he knelt in front of me and I could see he was hard again I must have had a surprised look on my face cos he said you didn’t think that was it did you and laughed, he lowered himself between my legs and I reached down to guide his cock into my very wet pussy holding his cock as it slid inside me, I reached behind him and pulled him onto me as he fucked me with long hard strokes his balls slapping against my bum cheeks with every thrust, I was in heaven and after a couple of minutes came with a loud moan (something that happens to me very rarely during penetration) he turned me on my side and lay behind me slipping his cock into me and reaching round and caressing my boobs I told him to squeeze them harder and he did as he bit my neck and shoulders this guy really knew how to fuck and I was loving every second he reached down and started to rub my clit in time with his strokes til I came again by now I needed a breather so I turned round and took his cock into my mouth so I could taste my pussy juices he went to climb on top so I said give me a minute to recover he said ok and turned me over and gave me a wonderful back massage, when I was recovered enough I raised my ass up and turned to smile at him he took the hint and slowly pushed his cock all the way into me then held my hips pulling me onto his cock as he fucked me hard and fast doggy I was unable to moan as the pleasure was so good, I moved forward off his cock and turned round to suck him again before getting up and kissing him again then pushing on his back I got above him and lowered my pussy onto his cock with my feet flat on the bed so he could see my pussy sliding up and down his cock after about 10 minutes I suddenly heard my name being called it was mike he had come back I stopped and looked down at tony and he said youd better go, no way not yet I said and carried on riding him with one hand on my clit bringing myself to near orgasm til he said i’m cumming and I bought myself to orgasm as he pumped me full of spunk, I lifted of his cock and bent down to suck his cock dry, you really do need to go now he said, I know i’m going I laughed.

I hadn’t been this aroused for a long time and I knew he could feel my nipples on his chest, he untied my bikini top and undid the clasp letting it fall to the floor and caressed my left boob as he kissed and licked the nipple of my other, I moaned with desire and pulled him closer loving every second he lifted me off the stool and carried me over to the pool table and I laid back with my legs open he pulled my bikini bottoms to one side and kneeling started to kiss and lick my pussy every time he licked my clit I moaned and pulled his head into me, I came twice before he came up and kissed me again so now it was my turn I pulled his trunks down while still kissing and started to caress his cock til it was nice and hard turning him round I pushed him back onto the pool table looking down I could see his nice hard straight cock and lowered my head to take him in my mouth his cock was about 7 inches and I managed to get all of it down my throat and stick my tongue out and lick his balls as he moaned, I really went to town licking up and down his shaft while caressing his balls and got his cock nice and wet so I could wrap my boobs around it and give him a tit wank lowering my head so I could take his cock in my mouth as it pushed between them, I looked him in the eyes and he just said “your fucking great at that” I know I said as I took him all the way again, I was wondering where the bedroom was for some more fun when he suddenly said I’m cumming I thought shit not already as I put the head of his cock into my mouth and wanked his shaft till he came in long spurts into my mouth which I swallowed, he looked up and pointed to a door and said with a smile the bathrooms there I smiled back and said what do I need that for, he said wow I love a girl who swallows sorry I didn’t last long but you’re very good at that, he got up and taking my hand led me to a door and into a bedroom with a huge bed I got on and he followed pushing me back and spreading my legs wide he began to lick my pussy again until I came then he knelt in front of me and I could see he was hard again I must have had a surprised look on my face cos he said you didn’t think that was it did you and laughed, he lowered himself between my legs and I reached down to guide his cock into my very wet pussy holding his cock as it slid inside me, I reached behind him and pulled him onto me as he fucked me with long hard strokes, his balls slapping against my bum cheeks with every thrust. I was in heaven and after a couple of minutes came with a loud moan (something that happens to me very rarely during penetration) he turned me on my side and lay behind me slipping his cock into me and reaching round and caressing my boobs I told him to squeeze them harder and he did as he bit my neck and shoulders this guy really knew how to fuck and I was loving every second he reached down and started to rub my clit in time with his strokes til I came again by now I needed a breather so I turned around and took his cock into my mouth so I could taste my pussy juices he went to climb on top so I said give me a minute to recover he said ok and turned me over and gave me a wonderful back massage, when I was recovered enough I raised my ass up and turned to smile at him he took the hint and slowly pushed his cock all the way into me then held my hips pulling me onto his cock as he fucked me hard and fast doggy. I was unable to moan as the pleasure was so good, I moved forward off his cock and turned round to suck him again before getting up and kissing him again then pushing on his back I got above him and lowered my pussy onto his cock with my feet flat on the bed so he could see my pussy sliding up and down his cock after about 10 minutes I suddenly heard my name being called it was

I was unable to moan as the pleasure was so good, I moved forward off his cock and turned round to suck him again before getting up and kissing him again then pushing on his back I got above him and lowered my pussy onto his cock with my feet flat on the bed so he could see my pussy sliding up and down his cock after about 10 minutes I suddenly heard my name being called it was like he had come back I stopped and looked down at Tony and he said you’d better go, no way not yet I said and carried on riding him with one hand on my clit bringing myself to near orgasm until he said I’m cumming and I brought myself to orgasm as he pumped me full of spunk, I lifted off his cock and bent down to suck his cock dry, you really do need to go now he said, I know I’m going I laughed.

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 put my bikini back on and grabbed by bits and went down his garden path to the gate then back up to mikes place he said he went looking for me but couldn’t find me so I told him I went for a walk along the beach which satisfied him, I saw Tony a couple of more times during the holiday including dinner with him and his drop dead gorgeous wife, but never repeated the sex but it was a session I will never forget, and I dumped Mike a week after we got back.

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? Next day, I felt great and wanted a repeat performance, never seen him since

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Just happened, I don’t know why, just went along with it, It was easy / convenient

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 didn’t give a clear ‘yes’, but didn’t give a ‘no’

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? Great sex

What was the WORST thing about this hookup? nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? no

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

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? no

What do you think about the Casual Sex Project? its ok

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