Lost Virginity to Older Brothers Fiancé

fantasy turned reality, a true story of a 14 year old me entering a 6 month consensual love affair with my brothers 21 year old fiancé. Still secret

It was an innocent crush on my older brother’s girlfriend, we had known each other for years. Back in those days 7 years apart was a big age gap. But, as I entered puberty I had developed strong feelings for her. She was smart, pretty and unattainable. After all she was taken and college age. I was by now a freshman in high school. Skinny, though athletic and considered cute. I was hardly a man.

I also was unaware, that she must have had feelings for me as well.I had only so much as French kissed girls while in middle school. Within the calendar year from 8th grade (December of freshman year) we would be regular sexual partners. It started that summer when her bf was away on a trip. She would stay with us quite often and since I shared a room with my brother she slept in the queen bed of theirs on the other side of the room.

One particular night I was lying on the floor face down and she mounted me on the back and whispered in my ear “I know you want to give me a massage” in a very seductive voice. I obliged and we went to her bed where she looked away and took off her shirt not revealing her double D boobs, but her bare back. She was bra less and pointed her finger towards the lotion and oils on the night stand. I lubed up her back and massaged it for hours. She must have felt my boner pressed against her ass.

As the autumn arrived my brother returned to college and she ended up living with us full time. I was now in high school and puberty was in full swing, however I was a late bloomer. I had developed pubic hair, but not much and I hadn’t even developed arm pit hair or any facial hair. We continued with massages and she would also reciprocate with giving me back rubs too. I still hadn’t seen her boobs, but she would tease with putting on my much smaller t-shirt while she would give me my massage. She had been quite thin in high school, she had put on some significant weight by the time of our intimacy. Though she still looked pretty and sexy. She hardly resembled the cheerleader she once was. I think this insecurity led her to really fall for me even though my age and the fact that I was her bf’s youngest brother.

The further escalation occurred about a month later, we would be home alone and we would lay down on the couch and I would play footsies with her. I would gently ride my foot up her legs and pull her pajama waistband up and down pressing her vulva and derrière with my toes. She would give me smooch sounds every time I pressed the right place.

One night I decided to lie next to her after our massage. She was lying down facing up. I put my hand on her stomach and reached down to her belly button I asked “is this your belly button” she said “yes” I then reached down further and started stroking her voluminous pubic hair and I asked “what’s this”? To my shock she didn’t flinch she just said “you’re a pervert” and apathetically let me continue.

A week later, I had returned home from playing at my friends house (mind you I was barely 14) I went upstairs to the bedroom and started creeping my hands down her pants again. This time the pubic hair felt different. I reached a bit more and slid my finger into her vagina, we both clutched each other’s hands and I fingered her for a half hour straight eventually getting 3 fingers in. Nothing was said, but we were both breathing very heavy. I fingered her over a couple of weekends, though we weren’t talking about or acknowledging our progression of intimacy.

It’s now December, I start to do my newfound duty of finger fucking her on weekends except this time she whispers in my ear “keep doing that, it feels so good” I then penetrate harder and faster, she rips up her shirt finally revealing the boobs I’ve been lusting over for years! She then starts making out with me and she’s a great kisser!! Her boobs are everything I imagined it to be. Her scent is permeating the bed and sheets. I’m sucking on her double d boobs when I decide to pull down her pajamas a bit for a better angle. She lets me pull them entirely off! I can now see the luscious vortex of her vagina and her alabaster curvy chubby body. Her pubic hair shone in the moonlight resembling an upside down fir tree. From the cleanest alpine environment. It was magical.

I thrust my fingers up her vagina soft and hard. She is now completely naked, in a fit of passion I throw my boxers off and she wraps her legs around my body. My rock hard pulsing boner tries to penetrate her vagina. However, she’s so enticed in anticipation of my dick her hips are up too high and I almost stick it in her ass! She smiled a bit, lowered her hips and I thrust gently into her wet vagina. We’re now having sex!! She pumps back with each of my thrusts! It feels so good!! Her boobs are in my face she’s caressing my back so passionately I’m also excited and quite in disbelief that I’m having sex. She’s my brother’s longtime girlfriend and she’s 21!! All this is going through my head as we’re making out and pumping furiously. I remember our tongues deep in each others mouth so sweet and warm when I feel myself shoot 5 consecutive times into her vagina!!! Oppps she’s not on birth control I remember thinking at that moment. After she felt me cum in her she gave me the sweetest smile I can still see it all these years later.I then sucked on her boobs and continued intercourse for another 20 minutes. When we were done we cuddled in each other’s arms and slept together for a few hours.

When I returned to my bed, reality set in. I had just betrayed my older brother, someone I looked up to and respected. I was also confused how I just had the ultimate intense experience of losing my virginity to his girlfriend, another person I looked up to. How did it come to this? Just 6 months before I was in middle school and now I’m no longer a virgin. I also was concerned I had gotten her pregnant because we had unprotected sex and she wasn’t on the pill. I was confused and sad. But, I also was filled with love and affection from her. We were both clearly attracted to each other mentally and physically. We let nature take its course and nothing was stopping us.

The next weekend, we had unprotected sex which confirmed at least at the time, we were in fact in an intimate relationship and the weekend before was no fluke . The sex went on quite regularly 2-3 times a week over the course of 7-8 months. We never actually discussed our love affair with each other. One time, when I had abstained out of my massive guilt for a couple of weeks she said “me and your brother are talking about breaking up” which hooked me back in immediately as we had a marathon session later on that night where she gave me a blowjob finally and I came in her 6 separate times. That June she started acting resentful towards me (looking back I think I got her pregnant a couple of times due to our lack of protection)and though we still were intimate our affair ended when she abruptly broke up with my brother. A part of me was sad and relieved. We had managed to keep our sexual intimacy a secret. I’m sure a part of her was ashamed that she was turned on by her boyfriend’s 14 year old brother and I know I was ashamed of fucking a 21 year old engaged to my brother.

We were an unlikely pair, I was scrawny underage and off limits. She was upset at her weight gain and failing relationship. Perhaps maybe that’s why we found each other in intimacy. We were both a bit lost, awkward and happened to fall in love. I never felt that I was taken advantage of and she was not a criminal, even though it was a naughty affair and technically illegal I would like to think, I know I do that she really enjoyed those times. We’re both grown up and well established and still see each other from time to time just as platonic friends . Though I don’t recommend this type of affair for a variety of reasons, I can’t deny what happened. Also, only me and her know of it and will take this one to our graves.

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anonymous Sex January 29, 2025 at 9:55 pm 6 0