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Losing my virginity to an older woman
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By (user no longer on site) OP
over a year ago
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Long time reader but first time posting. I was messaging somebody about my first time and thought it may make a decent story
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I’m a bit ashamed to admit I was a late starter - 18 when I lost my virginity. There was a barmaid in the pub I used to go to. She was older and not much to look at really but she was a laugh and we were flirty. I was out one Saturday night and had been around town and ended up back in this pub. I was d*unk and ended up knocking my drink, she’d just put on the bar for me, all over myself and soaking my jeans etc. She felt sorry for me I think and got me another drink but also handed me a towel to try and dry myself - I jokingly said maybe she could come and do it and rub me down. She didn’t but you could see in her face that she wanted to. I woke up next morning to Facebook friend request from her |
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By (user no longer on site) OP
over a year ago
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I accepted the friend request and thought nothing more off it. I was 18 and she was 40 - I assumed she’d just come across my profile, recognised me and sent a friend request. Few minutes later a message came through “how’s the head this morning” - I replied “rough as fuck, dunno what time I got home”. “Lol, you were a bit of a mess” she said “yes well I asked if you wanted to help clean me up but you declined”. Nothing else came through for a bit and then I got “maybe I can rub you in private instead  |
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By (user no longer on site) OP
over a year ago
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I didn’t know what to say initially. I’m hungover but I’m also a horny 18 year old virgin desperate for a shag. I decided to play safe “I’m not sure your husband would be too happy about you rubbing other guys lol”. She replied that what he didn’t know wouldn’t hurt him and she’d always thought I was cute but last night when I knocked my drink over myself she could apparently see the outline of my cock through my wet jeans and she was gutted she’d had to turn down the chance to rub my dry as “there were too many people about and I couldn’t trust myself to not let my hands wander”. Now obviously this turned me on and I messsged back “so you liked the look of my cock then - how about it I showed you more”. YES!!!!! was the reply back |
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By (user no longer on site) OP
over a year ago
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Now, as my profile pics show, I’m not adverse to sending dick pics but I thought I’d try and get something. “Well I gotta have something from you before I send you a pic of my cock ” and waiting. No reply and I though I’d fucked up so left it at that. Later that night I checked Facebook again and there was a message from her “send me your number then and you’ll get something”. I did and 2 minutes later I got a picture message of her topless squeezing her tits together. She wasn’t the smallest girl so her tits were huge and amazing. My mind went straight into horny mode so I pulled my hard cock out, took a pic and sent it back to her. Another pic message - a close up of her smooth pussy - “I want that in here. I’m just about to go for a shower and I’m going to rub myself thinking about your cock” |
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By (user no longer on site) OP
over a year ago
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Next morning I woke up to a message from her “Morning - have a good nights sleep? I was dreaming about your cock”. I sent her something back about “maybe we can make your dreams comes true”. Not actually thinking that it would go anywhere as obviously she’s married. I get a message back - “yes, next week my husband is on nights, you can come around to mine”. I had to ask “are you serious, you’re married” - she said yes she was serious but she was gutted that she had to wait a week. I messaged asked was she able to get out one night and she said yes. I asked her where she lived and as it turned out she actually lived in the same street as me (different part of the street but a weird coincidence) so, as it was close by, I suggested we meet one night at the beach. She agreed and we arrange to meet up the following night (this was in summer so lighter and warmer nights)
I went down to the beach around 9 the following night not expecting anything but found her waiting by the toilet block. She dragged me round to the far side and leant in and kissed me. Her hand reaching for the zip on my jeans before reaching inside and stroking my cock. She’s got a low cut t-shirt on so I pull it down to see her tits and start sucking on her nipples. She undoes the button on my jeans so no restrictions to my cock before crouching down and staring to suck me. Her tongue running up and down the underneath of my dick before flicking against my slit before taking me fully in her mouth. Fuck me she could suck a cock - even now nearly 20 years later I don’t think I’ve had a better blow job than that
I didn’t want to cum to quickly so I pulled her up to start sucking and biting on her nipples again, my hand going into her leggings and between her chubby thighs to rub her wet pussy. I started playing with her clit before sticking 2 fingers into her soaking wet cunt. She was moaning as I was doing that and sucking her nipples and her hand found it’s way to my cock again and she furiously started rubbing it and squeezing my balls. I took my fingers out and concentrated on rubbing her clit, want to to make her cum and I could feel her tensing and shaking as her orgasm built. Next think she let go of my cock as her pussy twitched and pulsed and she squirted all over my hand. She leaned against me to recover before saying “now it’s your turn”
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By (user no longer on site) OP
over a year ago
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Thank you for all the feedback guys - there is more but work is getting in the way at the moment of having the time to write it up. Hopefully get time over the weekend |
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By (user no longer on site) OP
over a year ago
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She pushed me back against the wall of the toilet block, squatted down again and started sucking me like crazy. I couldn’t do anything but moan and let her get on with it. She was amazing, sucking all the way down to the base and using her tongue along my shaft as it was in her mouth. Her other hand playing with my balls, rubbing and gently squeezing them. I could feel myself getting ready to cum so I told her and she just started sucking harder and faster before using her hand to finish me off. My legs were trembling and I told her I was gonna cum - she took the tip of my cock into her mouth and wanked me until I shot a huge load into her mouth. I collapsed back against the wall to stop me falling as she stood up - a huge smile on her face. She opened her mouth to show me my cum in there before she let a little bit dribble onto her tits. She closed and gulped then opened again to show me she’d swallowed before using her finger to scoop up what she’d dribbled on her tits and bringing that to her mouth to suck it dry. I wanted to fuck her there and then but she said no - Friday night her husband was on nights - she wanted me to come to hers then |
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"I accepted the friend request and thought nothing more off it. I was 18 and she was 40 - I assumed she’d just come across my profile, recognised me and sent a friend request. Few minutes later a message came through “how’s the head this morning” - I replied “rough as fuck, dunno what time I got home”. “Lol, you were a bit of a mess” she said “yes well I asked if you wanted to help clean me up but you declined”. Nothing else came through for a bit and then I got “maybe I can rub you in private instead "
you old charmer |
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By (user no longer on site) OP
over a year ago
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The days leading to Friday were filled with messages back and forth. Her telling me what she wanted to do to me, where she wanted my cock. Pics sent of her in lingerie, pussy spread wide, nipples hard. I honestly don’t know how I managed to do anything else that week other than wank
Friday finally came and I got a message. “He’s gone to work and kids are in bed, come straight in - side door is open”. I went straight there and found her sitting on the sofa - in comfy clothes but a nice smell of perfume. I went straight over and started kissing her. My hands running all over her body, squeezing her tits and ass. Rubbing her pussy over her leggings. Her hands were running down my chest and rubbing my cock before moving round and grabbing my ass. I broke the kiss and lifted her t-shirt over her head to find her hugs tits enclosed in a gorgeous blank and pink bra. I pulled the bra down and brought my mouth straight to her nipples, biting and sucking hard before moving to the other one. He hands at the back of my head pulling me deeper into her big fleshy tits and moaning and gasping with each suck and nibble |
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I was 19 when I lost my virginity and funnily enough it was this site. ( old profile ). She was 68 and I was up front telling her I was a virgin I think that exited her alot because after I told her that she wanted to meet that very day. So I did. I was a clumsy mess but it was an amazing experience she took the lead. And since then I have a massive kink for older woman |
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