Former Virgin

I'm nothing special in looks or build, never been called handsome either. I looked slender, but I was very fit and muscled and into martial arts. But I didn't do well with girls and at 5'5" I wasn't what they thought they wanted. My younger brother taller than me by 5inches and played football as a linebacker (college) was engaged to marry his girlfriend in March last year. I was going to the wedding, but not part of the wedding party. Which suited me, as I could attend the wedding and put in an appearance at the wedding dinner and leave soon after. That was my plan anyway, but I hadn't taken in the other family guests into my planning. One other was like me and would be unaccompanied at both the wedding and the dinner. My brother's soon to be mother-in-law (MIL) who was a widow of 5 years or so. My father would escort his soon to be daughter-in-law down the aisle, it was planned I be the companion of my future brother's MIL at both ceremony and the dinner. Only my sister realized one fact they had overlooked, they expected me to be alone. She asked what would happen if I came with someone, at first, they thought no chance of that. But it did make them finally asked me if I was coming alone, once I said I was they told their plan for me to accompany the mother of the bride. She had no other children, so I was it with my mother doing the asking I couldn't really refuse. I hadn't even met my brother's Mil to be yet as well. But on the day of the wedding, I met her for the first time. She was about my height without high heels, slender and gorgeous for her age. At least I wasn't going alone, I thought. After the wedding ceremony and at the dinner we got on very well. She knew about me from my brother most likely, but I enjoyed being with her. After the bride and groom left, I offered to drive her home, and she instead asked me to take her to my motel room to continue the fun as she called it. I'd booked into a motel as the family home would be crowded with relatives and I would be able to get some peace. Referred to as a loner by the family it was expected. But my now sister-in-law's mother wanted sex and saw me as the only perfect lover available. It was also better than returning to an empty condo on her own. It didn't take her long to work out I was still a virgin, but she took her time, and I improved with each fuck. Three fucks total and I checked out and dropped her home on my way back to my own home in the city. The following Friday I received a call from her, she was in the city, and she enquired if I'd a spare bed. I only had a one-bedroom apartment, and I was sure I'd told her that. Her response to me telling her again was good enough, so we stayed to Monday morning before returning home. Draining my balls all the weekend, unable to come back the next weekend as the happy couple would be home from their honeymoon. But promised to visit again the following weekend, I realized I was now her sex toy and liked the idea. Fucking her gave me the confidence boost I needed, I started asking girls out on dates and failed. But finally succeeded around the time my brother's MIL found another man she would marry February 2024. Sex with her stopped in December 2023, but she hadn't said we wouldn't get together again at the time, and I had to go away to finish a project. On my return I heard the news and was even invited to her wedding. I'd met a nice girl and asked her out and she accepted and so she attended the wedding with me. I proposed in July, and we married in September. She is now pregnant with our first child.