During the summer between high school and college, we had a new neighbor who wanted her family house re-stained and my Dad had the great idea that I could do it for them.
Just for some background, they were a young couple in there early 30’s with a couple of kids under 6. The house they bought was one that we had considered buying a few years earlier when we moved to the neighborhood. The wife, I’ll call her Ann, was very vivacious and friended my Dad pretty much right from day one. Dad was and still is a car guy and she liked cars more than her husband. They quickly bonded, but I don’t think they ever took it further than a friendship even though my parents’ marriage was coming apart at the wheels at that time. To say my Dad was attracted to Ann is a huge understatement.
That particular summer we were planning a car trip to the west coast from the upper Midwest to attend a big car event. We were taking one of dad’s cars with us to show and race in the event. Ann offered to come along for the ride and a few days out there. Here the adventure began for me. I was 18 at the time and had a girlfriend. We were both getting ready to leave for college, together. GF couldn’t go and Ann was a great travel companion for those of us driving. Mom wasn’t coming with us but would meet us there after the drive, so it was Dad, little brother, and I.
We spent the first night in Colorado, Ann in a visitor apartment at a family member’s condo, the rest of us in rooms within the condo. The next day we got as far as Salt Lake City and then the next day Sacramento, staying in three hotel rooms at each stop. By the time we got to CA, Ann was flirting so hard with me that I think Dad was getting pissed off. That night in Sac, we parked the car and trailer, went to dinner, and crashed out in the three rooms. As an 18-year-old and now three days on from getting anything from the girlfriend, I was horny as hell.
About an hour after dinner, Dad found someone trying to jack our trailer and car. Bro and I went to help, he was 11 or 12 at the time and didn’t pick up on the sexual tension in the group. After Dad sent us all back to our rooms, Ann reached out and squeezed my cock in the jeans and motioned for me to come to visit her next door. I went back with the little brother, then excused myself as he was fading, to go get myself a snack.
I was so nervous. I didn’t really know what was going to transpire. Knocked finally and was welcomed in. She was so damm cute. Nice pert titties, just like my girlfriend. We sat and talked and flirted and finally she made the move. We ended up shortly on her bed, making out and groping each other. Her in a nice little summer tank and a jean skirt that both fit perfectly. Soon my cock was out and she was showing me her skills in a master class lesson on how to please a man. Damm Ann was skilled in giving a handjob. Being 18, I lost it quickly. Being 18, I came right back to the plate pretty much instantly.
At this point, I finally started to take some initiative and went for those perfect B cups. The shirt came off with some help and darn it, the most gorgeous bra I had ever seen was right there in front of me. I love small ones, so I was in heaven sucking, biting, pinching, and playing as the bra came off. This has to be the point in my sexual education that I learned that I really like fine lingerie. The girlfriend had cute stuff, cut for a pert 18-year-old and I already had a kink with it, but now I’d seen the major leagues, I was hooked, and still am.
We were both conscious that we might not have a ton of time, little bro next door might come over, and Dad might try to search us both out for some reason. At that point, we moved pretty rapidly to remove my shirt and shorts along with her skirt. Being in that time and place, I was in my tidy-whites, she got them off fast. I found nirvana under her skirt, matching the bra was a perfect little pair of panties. We were rubbing each furiously, she was sopping wet thru the fabric and I was teenage stone cutting hard.
Ann didn’t waste any time. I helped get the panties off her. She then wrapped them around my swelling cock and was rapidly driving me to the brink again. The GF hadn’t learned that trick yet. I showed it to her later, and she never asked where I came up with it, but that’s another story for another time.
Her pussy was very excited and dripping wet. The clit was protruding and her labia were swollen perfectly. I was able to get a couple of quick licks and tasted a fabulous treat. She wasn’t wanting to take too much time, pushed me down on my back, and mounted me in one fast motion. I’ll reuse the word Nirvana. The GF was tight, Ann was super tight and so super wet. She loved to have her titties sucked and played with when riding cowboy (not a term I knew at the time) and I was more than obliged to just that. I also then learned that I could better control myself and prolong my own orgasm long enough to get her off. And off she went. Wholly crap she came. In retrospect, probably a squitter, another term I didn’t know for many years.
After she came, we changed position and I got the perfect sight of her small tits, perfect smile, and my cock sliding in and out. I came quick and huge. Large sticky mess in her pussy, she rolled me back over on my back and cleaned me up. What a rush, that was also a first instead of running to get a towel or wash myself off. We cuddled for a short time, then I dressed and went back to my room. Slept like a rock, and didn’t even think about the fact I’d just cheated on the GF.
The next day we headed down the coast and checked into the condo we had rented for the week, right on the beach and so damn cool. Mom was showing up for a few days later in the week and Ann was scheduled to leave before she arrived. Dad, bro and I were so engrossed in the activities of the event and getting the car ready, Ann shopped, hung out at the event and took walks on the beach. I’m guessing now that oblivious 18-year-old me had no idea that her marriage was most likely also failing and this trip was to get away from it for a few days.
The night before the Mom / Ann swap happened at the local airport, Ann came and got me to join her again in her room. Much like the previous night, we were excited by the reality that Dad and bro were in the same building. I had done some walking on the beach with her at night and we had talked some, but not about her situation or mine. Just flirting like a teenager who was infatuated. We continued that in the room, just without talking, only making out, groping, stroking, and fingering. I was in heaven.
We both knew this was our last chance and we took advantage of it. She was again in some fabulously expensive underwear, this time with a camisole instead of the bra. I loved the look and feel but couldn’t wait to get it all off again. Ann took her panties and wrapped them around my cock, this time making me come in them within minutes. We had been playing with each other on the beach walk, so I already knew her panties were sopped and her pussy was ready.
We repeated the process from the previous night and with a teenage cock, I was still hard and ready to ride it out for a while. We did just that for almost an hour. Looking back, I’m sure Dad could have figured it out. I ended up spending most of the night in there. Pretty risky now that I think about it for Ann to have pursued me and then let me sleepover. Little did I know it wasn’t over yet.
We got Ann off the next day and then got Mom from the airport later in the day. Wow, parents were not in a good place and the mood went to shit. The event was fun but Mom had enough and decided to fly home and not drive with us as planned. Also, little did I know what was going on there.
Dad was in a much better mood after Mom left and we had a good trip back to the Midwest. Instead of the planned overnight in CO, we kept driving and got home very early in the am, about 12 hours early. Dad told us to stay in the car and he would let Mom know were home then we would go get some breakfast. I thought that was odd. About 10 mins later Dad comes out pretty irritated and we head to breakfast. We get back to the house and Mom is there but soon leaving to go back to school a few days early, she was working on a degree in another city down the state.
I was ready to find my GF and try out some of what I learned, and boy we did. She never asked about my new advanced techniques as she benefited from having her first orgasms on a cock. We keep it up for a week. Rabbits.
Ann reminded me that I still needed to start/finish the stain job at their house. I was trying to start to distance myself now that we were home. It didn’t work. She wanted to “thank me” for the stain job and invited me to join her for dinner and play. GF knew all about the stain job, said, of course, you should go, so I did. We had a great dinner, but boy was I was nervous as a cat on a hot roof being out in our town with Ann. Did I say she looked so freaking hot? Cute summer dress legs showing and obviously no bra.
The play was interesting and fun. Ann kept reaching over and stroking me through my khakis. It had a huge wet spot that I had to hide after the play. Of course, we went straight back to her house. Kids and husband nowhere to be seen. She was suddenly un-restrained and wild. The bottle of nice red wine came out and we killed it and another just sitting, snuggling, and stroking. But this was different than being in CA at the beach house or in a hotel room, I was way nervous he would show up or GF might even come looking.
Eventually, we moved to her king-size bed. She was ready and waiting for this. The candles were out, the sexy negligee was on the bed, lighting was just right. I wanted to bolt, I was nervous, but who could do that.
She was in this most gorgeous pair of dark blue real silk panties, and a tiny little camisole under her dress. I didn’t want her to take them off, but the negligee was so pretty, I didn’t protest. It was of a similar design, also pure silk and just a tab bit lighter than the fabric weight of the others. For some reason, I remember Natori was the brand, I had to look.
I helped Ann change. What a glorious process that included much pinching of nipples, kissing and stroking. She stripped me naked in a flash and then had me lay down on the bed. Nice sheets, very nice sheets. Like I said this was a planned event. Then the teasing started. First, the panties wrapped on the cock, then the nighty softly flowing across my body as she kissed hugged pinched and stroked. Okay, I was liking this, a lot. A lot, a lot. Older women, built like I wanted, married and cheating, and I guess I liked cheating too if it was this good.
We satisfied each other for a least an hour. I was again getting nervous that the GF would come looking. Ann didn’t want to rush, so I rode her out figuratively and with great pleasure. To this day I don’t know how she was so tight after giving birth twice already. I’ll never forget the sight of her on top of me again, nighty flowing as she rode up and down, up and down, in reverse cowboy with me reaching around from behind and playing with her nipples and clit thru the fabulous silk.
Like all great things, I came hard after she turned and let me take her from behind, and our time together came to a screeching halt. We cuddled and I dressed urgently to try to not get caught. I did ask where her family was finally, they were at a friend’s cabin with his parents and would be back the next day. That was the last time we got together. But it was glorious. We saw each other “socially” the rest of the summer, I even finally got the staining done at her house as I did it when she wasn’t home.
I didn’t know until years later what transpired at my house the morning we returned from CA. My parents had a huge fight in CA, obviously, as my mom was finally deciding that she was ready to leave the relationship. Dad knew something else was up and suspected she had a “friend” and he found out she did when we arrived home 12 hours early. Her friend from school was in bed with her that morning and dad found them in a 69 at 6 am.
Bummer way to find out your wife of 20+ years and high school sweetheart had determined that she is in fact a lesbian. They divorced that year after I went back to college. All for the better, but I will never forget dad saying “I could handle it better if it had been a man”.
As for Ann, I later found out that she had an open relationship with her husband, at that time not very common. She was playing the field and so was he. Turns out the night I was with her in their bed, he really wasn’t at the cabin with the family, but having his own fun time somewhere else in town.
MANY years later, little bro finally put two and two together and figured out what went on during the CA trip. He caught me in a lie and I grudgingly confirmed it. Of course, he made sure my older sister knew about it along with my wife. This made for some interesting conversations with all parties. Sister was pissed, brother was jealous, wife was curious (now knew where a couple of my kinks and techniques originated) but reasonably understanding. We all wonder if Dad and Ann ever got together. He’s not talking but got re-married a short time later, so I don’t think they did.
That summer will be with me until I die. I still love lingerie (maybe too much) and I learned some great techniques. Ann was a very skilled lover and I benefited from it immensely. My GF and I broke up about 18 months later. It had become long-distance and we wanted different things. I had my eye on a cute girl in one of my classes shortly after that and moved on with life. I still yearn for great lingerie, even more now about 40 years later. So much so, that I wear it sometimes myself. I know, Kinky.
Source: reddit.com/r/gonewildstories/comments/gg0z8i/my_affair_with_a_mature_f_neighbor
Amazingly sexy story! Thanks for sharing.