So in my last story I talked about how I had hooked up with my little sisters roommate which caused them to get into a fight that led me to staying over and hooking up with my little sister.
This time I’m gonna start talking about my times with my little sisters roommate/best friend. Now for clarity me and her had an on going thing for about 2 years never really getting together until about a year into it after I had lost my vCard and had gained some confidence. That being said I probably wouldn’t be where I am today without her and the boost to my self esteem that started with her.
Ok background I grew up in a very strict Christian home and because of that I for the majority of my life had thought that I should wait until marriage to have sex. I had a very long and serious relationship that had started in high school and went on until I was almost out of college. She was a missionaries kid so we never went further than a little bit of oral but it led me to be awkward about sexual situations sense I was under the impression that sex was something that only people “in love” could do.
It took meeting a girl and excepting that I was ok with losing my virginity to her without the title of a relationship that I began to really consider having sex without a huge emotional commitment.
Hence meeting Ray from my last story. Now like I said me and Ray were just friends until after I had hooked up with her roommate but I was ok with that. That being said her roommate was a different story. I met her early one morning when my little sister asked me to pick her up after a night of drinking.
I drove out and met them both Ray sitting in the front seat of my car and her best friend Abbie sitting in the back. Now Abbie is the perfect opposite of Ray when it comes to looks, where Ray is petite in every way Abbie is perfectly curvy. She has huge 38G tits and a perfectly round ass. She has dirty blonde hair that she shaves on the sides.
My first thought of her is that she must had been a giant sense standing next to Ray she was at least three inches taller, but I later learned she was wearing heels and is actually the same height. Now I drove them to Abbie’s house and as I did I was making a few different jokes and was getting Abbie laughing in the back.
I got to her house and as she was getting out of the car I opened my phone and saw that she had friend requested me. I accepted and didn’t think anything of it until the next day. I was at home cleaning up and I opened up Facebook and saw she was online.
I sent her a message and we started the normal small talk. We went back and forth until she asked if I wanted to hang out. I knew I really didn’t have to much to do today so I responded with sure and she said she was hanging out at the local library.
I drove and picked her up and we started talking mostly innocent stuff then I brought up something about how I couldn’t draw to save my life. She said she was a great artist and I asked if she had any of her stuff with her. She said yes but that I would have to wait to see them sense she didn’t want to distract me while we drove.
We got to my place and I led the way into my room and started watching movies on Netflix as she showed me her drawings. Mostly anime girls but one struck me as pretty hot.
I pointed to it and said, “I like this one she has rockin tits.”
The girl in question did have giant tits and was pretty similar to Abbie but I didn’t put two and two together until she responded, “Well that’s actually a self portrait.”
I looked at her then at the picture I raised one eyebrow and said, “I don’t know. Are your tits really that big.”
She looked at me blushing a little and said, “Well if your curious about them…”
She let that statement hang in the air between us as I looked at her and she at me. I leaned in closer to her and kinda froze. At this point I hadn’t so much as kissed a girl in over two years and now I was talking to a girl I had met the day before about what her tits looked like.
I leaned forward finally and pressed my lips against hers. Not really what I would now call a kiss but most certainly just testing the water to see if she would respond positively to me showing physical attraction to her.
She pushed into my kiss and we started to actually kiss and I reached up and started to massage her giant tits. I felt her bra and was astonished by how thick it was (only having my ex who always wore a sports bra to compare) I reached around and under her shirt and unclasped her bra using only one hand. She broke our kiss and chuckled and asked where I learned to do it and I just said I’m magic (truth is there’s a video online that taught me)
I pulled her bra up and revealed her tits I started to suck and twist and pull on her nipples getting her to moan and gasp as I went. I slowly slid my hands down her sides and tried to push her pants down but she stopped me hesitantly saying that she was currently on her period so we couldn’t go all the way.
I didn’t mind to much in my weird virgin mind sense it was just fun kissing her and getting to fondle her tits but I wondered how far she would let me go. I started kissing her again and grabbed her hand and pulled it down until it was on my hard cock straining thru my jeans. She slowly stroked it then started pulling at my belt. I rolled over letting her get my belt off and pulling my pants down so my cock sprung free. She moaned slightly and whispered how she wish we could go all the way sense I had such a nice cock.
We started kissing again with her slowly stroking my cock and me playing roughly with her tits. We were moaning into each other’s mouth and we’re going at it for a good half an hour me getting my pants all the way off and her her shirt. She spat on my cock to get it wet and even let me tit fuck her for a bit but we mostly just were kissing and playing with each other. After a while her hand started to cramp and I asked if she could finish me with her other hand she said yes and vigorously started to pump my cock until I felt myself explode sending streams of cum everywhere all over her tits and hand and even (as I later discovered) on the ceiling of my room.
We cleaned up using some towels and I drove her to go get some pizza. We spent the night eating and her showing me nudes of herself and me playing with her tits.
I dropped her off at her place with plans to hang out again in a couple of days. I thought I had a pretty good thing sense I was thinking it’d be cool to finally lose my vCard but it wasn’t to be yet.
I called my sister that night and in my stupid mind I had convinced myself that I liked Abbie. Ray told her that and Abbie quickly broke off the thing between us. I understood but still to this day I’d say I got a bit of a thing for her. Not emotionally but definitely sexually sense we have such good chemistry.
This is the first part of a long story between me and her which ended with me and her on ok terms but also having hooked up a couple times and her eventually cheating on her bf with me. But those are stories for another time.
(Thank you everyone for your support on my last story. I’m gonna keep writing these because it’s a lot of fun and I happen to have a few now. If you got any questions you wanna ask just ask I’m a pretty open book when it comes to stuff)
Source: reddit.com/r/gonewildstories/comments/66us4c/my_sisters_roommate_part_1_mf
RemindMe! 7 days
You keep calling her your sister yet she’s not your sister.