I Wonder What Could Have Been

This happened about six months before I got together with my future wife. My wife and I have been married for more than 35 years and we’ve been able to retire comfortably in a beautiful area of western Canada. Our relationship has virtually leaked sex in all its forms and it’s always been difficult to keep our hand off of each other. No complaints at all and we’ve been scrupulously faithful from day 1. Sometimes my brain wanders off and I wonder what could have been with the subject of this story (a petite woman named Angela who was five years younger than me and an only child). She was sexually inexperienced and I taught her a lot in the short time we were together. Her parents were filthy rich and for some reason really liked me. 

I had gone to university after deciding I wanted to pursue a professional job. There was a woman in my program (Kelly) who was the same age as Angela and friends with her - Angela was in a different program than us. I would notice Angela often hung around with our group at the student pub, etc., and caught her looking at me frequently. Being the shallow horndog I was, I didn’t pursue her obvious interest on the basis that her tits were on the small side of medium and I liked big ones. One day Kelly awkwardly approached me and said Angela had a crush on me and wanted to go out with me. Kelly told me that she’d known Angela for quite awhile and warned me that she was a bit weird and quite jealous and possessive; she told me to be very careful if I got into a relationship with Angela. I should add that Kelly and I were strictly platonic friends and she wasn’t trying to “keep me for herself” or anything like that.

I was therefore standoff-ish without being rude to Angela. One fateful day she asked me to help her study for a French exam. She said she’d cook me a nice dinner if I helped her out and that we could study at her parents’ house as they were away for a few days. All the signs of a set-up, but I had heard Angela was a great cook and I was horny, so what the hell…let’s see what happens.

I got to the parents’ house and was treated to a really excellent dinner by Angela. We moved to a different table and cracked the books, but it soon became clear that the only French Angela was interested in that night involved mouths. She flat-out asked me take her to her bedroom and I told her the living room couch looked good to me. We went there and started passionately necking and I soon had Angela’s shirt and bra off. Although her tits were quite small, they were firm and shapely and her nipples were really big and long for the sucking. We lay down on the couch and I started dry humping her hard. She said I’d have to use a condom and I didn’t have one, so I told her so and that we’d have to do something else. Eventually, I got her skirt off and kissed her pussy through her sexy panties, which had a very noticeable wet spot in the crotch. I got her naked and asked her to sit on the couch so I could assume my favourite kneeling position. She did and I started eating out her very hairy cunt. I’m really good at cunnilingus if I do say so myself, and I got her off twice, moaning loudly, in maybe 15 minutes. I had dropped my jeans and underwear and was stroking my thick cock the whole time.

I told Angela it was my turn, but she said my penis was too big for her to comfortably suck. I told her I’d be happy with a handjob and she proceeded to whack my cock hard as I sat beside her on the couch. I told her not to be so rough, but she really didn’t seem to grasp (nyuk nyuk) the concept. I was getting close to cumming so told her I’d “finish myself off.” I got her to lie on her back and straddled her hips. I jacked myself long and slow, edging myself a bit, and finally went for it. I jerked myself faster and blew a huge load all over her torso. It felt so great as I blasted rope after rope on her, the cum kind of melding together in a warm, white pool of pleasure juice.

I fucked Angela a few times after that and she learned quickly, but there no way it was going to work - she was just too damn clingy. Still, it would have been nice to get into a life in that house at some point…