Story Details

Taking my Girlfriend's Sister to Prom

maxxxpassion on Taboo Stories

I love a woman with dark hair and light nipples! They always make me cum the hardest. I remember the first time I saw a dark brown haired girl and her light nipples. It was my girlfriend’s sister. She was getting ready for Prom, no joke, and needed help zipping up her dress. Her dress had a side zipper, so when I walked up the stairs and into her room the front of her dress was almost fully revealing her amazing breasts. She was very pretty, young firm D cups, small waist, with a very firm round ass. Her sister was exactly the same, but blonde with A cups. I instantly got hard and when I walked up to her she told me what she needed. I looked at the side of the dress and gave her a sideways smile. She asked why I was smiling and I admitted to her that I had seen her breasts and that they were beautiful. She was taken aback, but didn’t move her arms to secure her dress or ask me to leave. The interesting thing about her was that she was very liberal with her body. She never really cared if I saw her in her underwear and I had never really thought about it until right now . . . maybe she wanted me to notice her. I didn’t think she had left the dress open on purpose, but she wouldn’t think to make sure she was covered up completely before I came to help. My pulse quickly started to race and I decided to take a huge risk.

I went around behind her to make it look like I was about to help her with her zipper but instead pressed my hard cock into her back. She just froze and we looked at each other in the mirror. I kissed the side of her neck and she just inhaled and held her breath. She didn’t say no, she didn’t move away and didn’t ask what I was doing. She wanted this and was waiting for what I was going to do next! We were facing her mirror me behind her, so I slowly peeled her dress down to expose her breasts. She breathed hard and quick and I just stared at them. Oh my God they were almost perfectly proportional and the same size. Beautiful light pink nipples and amazingly perky, which isn’t surprising for an eighteen year old. I reached up with my left hand and slowly cupped her left breast and rolled her erect nipple between my thumb and index finger and she started to breath even faster. I was overcome by passion, so I pulled the dress down completely revealing her whole body only covered by a thong. 5'2", a big round firm butt, D cups and she was beautiful. I reached one hand down towards her vagina under her underwear and she tried to stop me, but I reached her clit first. I rubbed it for a few seconds and she was almost instantly wet and now she was under my control. I pulled off my pants and sat on her bed facing the mirrors and pulled her onto my lap. I removed her panties and spread her legs so she could see me rubbing her pussy. It was beautiful! The outer lips of her labia were plump and curved in around her inner lips. When she spread her legs she was already engorged. She was soaking wet and I used three fingers to rub her entire pussy and clit. I stopped a few times to stare and take her in. She was now almost laying fully back on me and all I would see was a heaving chest with amazing tits, followed by her firm spread legs and her amazing pussy. She was a Goddess built to please men. She always received attention from her boys who were friends. She almost never dated and here I was bending her to my will after being forward and aggressive. I thought that she must have wanted me all this time, so I went further.

After getting her close to orgasm I reoriented sitting on the side of her bed facing the mirrors lounging against one of those pillow chairs, her back against my chest and put my cock between her legs and rubbed her pussy with it to get it as wet as possible. I had no idea if she was a virgin or not and I wasn’t going to ask. My guess is that she was at the time (I’d find out later I was correct). To be honest I didn’t care. I had shown an enormous amount of self-restraint to this point, so I slowly put my cock inside her. It looked amazing slowly sliding into her. She gasped hard and dug her nails into my forearms! I was very gentle because I was betting she was a virgin and I wanted her badly and didn’t want to have to stop. I had her lift her head up to look in the mirror and watch my whole dick disappear inside her and she loved it. She reached down to touch what she was seeing and cupped by balls. I fucked her slow and deep while rubbing her clit softly after I was fully inside.

Since I had been fucking her sister for the past year I knew what a pussy felt like when a girl is getting close to orgasm and this beauty was getting close. Her pussy was getting so tight. She was starting to gyrate her hips and since we didn’t have a lot of time I decide to try and have us cum together. I started rubbing her clit faster to help speed up her orgasm because I was at the point where she was about to make me cum anyway. I rubbed faster, and she covered her mouth with her hands to keep herself from yelling out. Her orgasm started to tail off so I started pumping faster and filled her young pussy with my cum. It was so hot watching my cock pulse in the mirror as I filled her up, some running out as I stroked. When I pulled my cock out cum rushed out of her stretched pussy. She just stared in the mirror for a few seconds and then said the first words since this all began -- “oh my God you came so much . . .and inside me.” I whispered a response in her ear “I wanted to send you to Prom with a piece of me inside you.” She smiled so big her face almost looked contorted and then she just laid back down, her back against my chest. Her legs were still up and spread, so I took a chance and started to play with her never touched asshole. Shocked, she closed her legs around my hand, but I slowly opened them again. Using my cum as lube I inserted my finer inside. She said "oh my God, no you can't..." But just laid still as I fingered her ass. She loved it. She whispered, “oh my God, no that’s the wrong hole.” And I responded “I know, I want to feel your ass too. You have the best butt I have ever seen I want all of you.” She wrapped her arm around the back of my neck and I knew I had her ready again.

I knew I had to fuck her ass while I had the chance because she was completely wrapped up in the experience and her sister would be home within the next ten minutes and her parents were down stairs. But I was still spent from fucking and cumming inside her only a couple of minutes before, so I told her to flip around and suck me while I fingered her and she didn’t even give my request a second thought. She probably just thought I was going to play with her ass while she blew me, but she was wrong. She was giving me a very good blow job, she obviously had done this before, and when I was ready again I put her on her knees with her facing the mirror and put my thumb in her ass. It was so tight. I used my cum as lube again and tried to enter her ass with my cock, but it was too tight. She almost screamed, and she said “It’s too big it’s not going to work. I have lotion on my nightstand, but hurry.” I grabbed the lotion from her bedside table, but it didn't want to work either. Her ass was just too tight, and we didn’t have the right lube. By that time, I was so horny again I just decided to fuck her pussy because I needed to cum. When I entered her from behind she looked right at me in the mirror with a look of surprise on her face. And when my cock hit her cervix she bucked with pain. Again, I started fucking her slowly, but kept my cock deep inside her. It was such a turn on watching myself fuck her from behind. She was so wet and tight. I just found myself trying to move my cock around inside her pussy because it felt so good. Within minutes I was ready to fill her eighteen year old body with more of my cum. When I was about ready I grabbed her amazing ass and her long brown hair and went balls deep and felt my cock shoot my cum deep inside her. My cock was pulsing, spewing hot sperm inside my girlfriends sister for a second time in less than ten minutes.

If she wasn't on birth control she would have gotten pregnant for sure. Luckily, I knew she was because I had seen her take her pills, so I came inside her without worry. After pulling out I just stared at her gaping pussy as it slowly closed and tightened. She hopped up, but on her panties and rushed to get her dress on. I threw on my shorts and helped. Five minutes later my girlfriend got home from work and fifteen minutes after that her date showed up to take her to Prom. I just smiled knowing she would be going with a pussy full of my cum. Before she left she caught me in the hall and gave me the most passionate kiss. She whispered in my ear "it hurts when I walk, but I want to do that again." I smiled real big and my girlfriend came around the corner and said laughing "why are you guys smiling so big, what's the inside joke!?" I burst out laughing knowing my cum was inside her sister and said "oh nothing, your sister is just so excited to go to Prom!"

Who knew this was the start or an almost two decade long affair that I will write about in future stories . . . stay tuned!

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