This is a true story of a hook up I had a few years ago that I think about quite a lot.
I started going out with this girl Clare when I was 21 at university. After a few months I went to her house and met her parents and her sister, Rachael. The second time I went to her house her parents friends were there with their daughter Lilly, who was best friends with Rachael. Lilly and Rachael were both 15 at the time.
I could tell pretty quickly that Lilly had a crush on me because she was acting shy and awkward and kept glancing at me then looking away quickly.
I dated Clare for 2 years in which time I regularly stayed at her parents house. Lilly was there quite often so I got to know her a little bit over time.
Eventually me and Clare broke up. A couple of years ago when I was 25 I noticed that Lilly would like a few of my pictures on Facebook, she was 19, I thought she looked cute so I liked some of hers (I know it’s lame but that’s how it started). I didn’t want to message her out if the blue because I thought it would be awkward but luckily she messaged me asking to complete a survey for the sociology course she was doing at university. She sent it out to like dozens of people I could tell by the message but I messaged back and said I would be happy to complete it and this got us talking and catching up. She was at university in the south of England and I was living up north. I lied and said I was going to be coming to the city she was in for work and it would be cool to get a drink. She said that would be great and we set up a date.
A couple of weeks later I got the train south and met up with her. She’s about 5’2 and what people call thicc, a nice big bum and boobs. She has a cute face and wears black glasses and her hair is shoulder length and hazel brown. She’s got a bit of a posh accent and is always very polite. It was a little bit awkward at first because we hadn’t spoken much when we knew each other a few years ago but we started to click pretty quickly.
We went to a restaurant and got some food then went to a bar and had drinks. We started flirting back and forth as the alcohol kicked in. She asked me if I wanted to see the student dorms she was living in and they were only a 10 minute walk away. I said yeah and we went back to hers.
When we got up to her floor two of her roommates were watching a film in the living room and looked pretty tired. We didn’t want to interrupt them so she asked if I wanted to go to her room, do we did.
We were in her bedroom for 5 minutes and both sat on the bed. I leaned over and kissed her ran my hands on her thigh. She kissed back and put her hands on my chest. I could tell she was a bit nervous so I took the lead. I felt her boobs and gently pushed her down on to her bed and lay on her and kissed her and unbutton her shirt. I took mine off while she finished taking hers off. I pulled down her trousers and took them off too, then took mine off. She was wearing lacy white matching underwear.
We kissed for a while and I started rubbing her pussy through her knickers, I could feel the warmth coming through them and knew she was wet underneath. Still kissing I slipped my hand down under her underwear and felt her smooth mound, then went further felt her wet pussy lips so I ran my finger between them and parted them and pushed a finger inside her.
My cock was hard at this point and she reached down she grabbed it and gently squeezed it. I kept fingering her she rubbing her clit.
I pulled her knickers off and saw that she was freshly shaven, and she pulled my boxer shorts down. I stood up with my cock was fully hard and she came to sit on the edge of her bed. She grabbed my dick with one hand and started sucking the head slowly, then licking it and making it slick. I reached down behind her and unhooked her bra, she wriggled out if it, sat up straight and started to properly sucking my cock taking it to the back of her mouth and it was jabbing against her tonsils. She was lifting it up and licking from the base to the tip with big wet licks and when she was finished there was thin strings of spit connecting her lips to my glistening cock.
She laid back and revealed her tits to me for the first time, they were big and nicely round. Her nipples were big and soft and pink. I got on top of her and kissed her again then moved down and took one if her nipples in my mouth and sucked it. I pushed bother her boobs together and squeezed them gentlely, sucking both of them a few times. Then I kissed down to her pussy and stated licking her clit which tasted sweet and fresh. I pushed her legs up and licked and sucked on her pussy lips which were very wet now. I slid a finger inside her and slowly fingered her while I licked her clit. She moaned softly.
I realised I hadn’t brought a condom and asked if she had one. She didn’t but she said she was taking birth control pills. We both decided it was fine and continued. I kneeled beside her and put my cock near her face. She sat up and eagerly sucked my cock again only for a few seconds to get it wet again then I got on top of her. I parted her pussy lips with my cock by running it up and down her slit, then pushed inside her.
I kissed her as I started to thrust inside her and she spread her legs wider so I could go deeper. I took one of her tits and started to suck her nipple while still fucking her. She moaned louder now. We fucked on this position for a while she she put her hands on my hips and started to pull me in to her faster and harder, I liked this because I knew she was really getting in to it.
I pulled out of her and sat back in my heels and pulled her hips to let her know I wanted her to get on her hands and knees. She got up on her knees and before turning over She lowered her head down and had another suck on my cock. It was only brief but I loved that she was tasting herself on my.
When she was finished she turned around and got on all fours, presenting her holes to me. Her wet pussy looked great she she had a tiny little pink arse hole just above it. I positioned myself behind her and slid my stuff cock into her pussy. I started slowly and gently pushing it all the way in then taking it almost all of the way out and repeating it. She started to push back on me letting me know she wanted it faster. I built up the pace slowly but before long I had my hands on her hips and was fucking her quite hard. She was moaning in to her pillow trying to be quiet.
Whilst still fucking her I leaned forward and reached underneath her and found her clit. I started to rub it while still thrusting deep in to her. After about a minute of rubbing her moans changed and I could tell an orgasm was building up in her, her breathing became deep and her back arched. I felt her pussy squeeze tighter around my cock and her hips began to jerk. I kept rubbing her wet clit slowly throughout her orgasm for about 10 seconds until she pushed my hand away when it became too sensitive.
Her pussy was still clenching and releasing my cock so I knew she was still enjoying the pleasure. I grabbed her hips again and deeply fucked her knowing I was about to cum too. I couldn’t resist rubbing her little arse hole with my thumb for the last few seconds of our fuck.
I felt it build in me and I slowed my thrusts as I shot my cum deep in her cunt. It was a strong orgasm. When I was finished I pulled my wet cock out of her and sat back on the bed. Lilly turned over and looked back at me and smiled. Her face was flushed red and her glasses were wonky which I found cute.
She sat up and I asked her if I could watch my cum drip out of her. She smiled and looked a bit embarrassed but she said okay. She laid back and pulled her legs up. After a few seconds my cum started to leak out of her pussy and run down her arse. I rubbed my cock slowly while watching the show.
I spent the night at Lilly’s that night and in the morning we went and got breakfast before I took the train home. We messaged back and forth for a while after that but things fizzled out after a month or so as things do.
This was about 3 years ago and she’s engaged now. I loved that night and still think about the sex we had quite a lot. I think it’s because she wasn’t a slut she was just a nice regular girl she that made it more hot to me somehow.
Source: reddit.com/r/eroticliterature/comments/if41nd/me_and_lilly_non_fiction_mf