Older Brothers Fianc? Took My Virginity

It was an innocent crush on my older brother’s girlfriend, we had known each other for years. Back in those we had big age gap or so it seemed at the time. But, as I entered puberty I had developed strong feelings for her. She was smart, pretty and unattainable. After all she was taken and officially engaged to my older brother! I was a growing high school boy. 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 school. Within the calendar 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. Just me and her sharing the room in separate beds on either side of the room. 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 me by slipping into my much smaller white t-shirt while she would give me my massage. She had been quite thin in high school, but she had put on some significant weight by this time. Though she still looked pretty and sexy. She hardly resembled the cheerleader she once was and was now a thick size 18 (I only knew that because I had snagged a pair of her panties to stick my nose into and embrace her scent🤣). 

I think this insecurity led her to really fall for me even though my age, I also gave her a lot of attention and physical touch with our bare back massages almost every evening. Slowly teasing each other with each rub and mounting each other’s back side pressing our erectile regions through our clothes. It was very hot and heavy.

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 derriere with my toes. She would give me smooch sounds every time I pressed the right place. I could feel her lips swell and warm up as I pressed through her cotton pajama pants to her vortex of seduction. She just let me push and pull to my heart’s content.

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, I went upstairs to the bedroom and started creeping my hands down her pants again. I started stroking her pubic hair and she again didn’t refuse my advances, with my hands down her pants! I reached a bit lower and I felt something wet and warm I slowly and gently slid my finger into her vagina. This was my first time fingering a girl, I put in a second finger and was moving them up and down pressed against her clit. I had no idea what I was doing, we both clutched each other’s free hand holding them with interlocking fingers. 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 that month of November, though we weren’t talking about it we were getting more into each other.

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 to finger fuck her. 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 months ago I couldn’t imagine even so much as holding hands and kissing her and now she willingly and excitedly took my virginity! To top it off I just came inside her without protection! It was a lot at once for my young brain to process. I also was concerned I had gotten her pregnant because 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 again had consensual 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. 

 I had abstained from sex with her out of my massive guilt for a couple of weeks. Then about 5 months into our relationship (Early April) she said “me and your brother are talking about breaking up” it was out of nowhere and I took it as a hint that she didn’t want me to stop having sex with her. Of course my intuition was right as we had a marathon session later on that night where she gave me my first blowjob and I came in her 6 separate times as we fucked until sunrise. 

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 youngest brother and I know I was ashamed of fucking a 21 year old woman engaged to my brother.

We were an unlikely pair, I was the scrawny and annoying youngest brother of her fiancé. She was unfulfilled at her weight gain, uncertainty of a wedding date 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 know that she really enjoyed those times even though it was forbidden. I think it was a big turn on for her to take my virginity and guide me to manhood. 

We’re both grown up as this was years decades ago really. We’re both 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. I’ve learned to accept that’s how I lost my virginity. Through desire, unwavering attraction and unlikely love. As bad as it sounds, it was the hottest sex I ever had, and she would probably say it was the hottest sex she ever had.