I was in my hometown recently visiting my parents for a week. Every night when I got into bed, I recalled memories of the few times that girlfriends ever stayed over and the fun that was had when, without fail, we would find ways to fool around undetected.
** ONE **
The first memory is from my senior year of high school, when I was 18. We’d had a big party for my father’s 50th birthday, and my girlfriend had been in attendance. The party finished late, and my girlfriend had permission from her parents to stay at our house since my parents were home, and with the promise that we would sleep in separate rooms. Of course, we broke that promise. While the party was still happening, my girlfriend and I were able to have some time to talk privately, and we agreed that at 1 AM I would come to her in the guest room.
We hadn’t been dating all that long, but we had fallen hard for each other. We were each other’s first real loves, and as 18-year-old love goes, it was real. Neither of us had much sexual experience and we were still kind of figuring things out. Making out that night was the first time that she let me take her bra off and kiss her breasts. I think she’d had her top off for her boyfriend before me, but I never asked and she never told. Her breasts were small, not something that you could even really cup, but they were perfectly formed. I thought it was going to be my first time seeing a girl totally naked, but she wasn’t ready to go that far and she left her panties on while we made out.
But it was the first time that I was naked in front of a girl. I was on my back when she took my underwear off, becoming the first girl to touch my cock. Again, I have no idea whether or not she’d gone that far with her previous boyfriend — I didn’t want to know — but she seemed pretty tentative, so I told myself the answer was no. Then I was on top, touching and kissing her breasts while my cock rubbed against her pussy, occasionally getting caught for a second as it tried to slot its way in but was stopped by her underwear. I’d never been so hard in my life and her underwear was soaked with her pussy juices. Eventually we switched again, I was on my back and she got on top of me. I had perfect access to continue using my mouth and hands on her breasts and she was grinding away on my lap. I warned her that she needed to stop unless she wanted a mess, but she kept going. And that led to the first orgasm that another person ever gave me — cumming all over both of our stomachs and her underwear. When we got cleaned up and I looked at the clock, it was 3 AM. That is 2 hours that I remember very clearly even though it was many, many, many years ago.
** TWO **
The next time that a girl stayed over is a time when I was home alone, probably 7 or 8 months after the story above. It was the summer after high school graduation but before leaving for college. The girlfriend from above and I had a lot of fun and went a lot further in those months, and we had only recently broken up in advance of college. Meanwhile, my parents had to attend a wedding that was a 3 hour drive away. The wedding was on Saturday and there was a brunch on Sunday morning, so they were gone from Saturday morning until Sunday afternoon.
I took advantage of the situation. There was a girl who graduated with me with whom I’d had sexual tension for the last 3 years of high school. In particular, during our sophomore years we’d agreed that we would play a game of strip poker with each other prior to graduation. We reminded each other of this in a flirty way once or twice a year — the last time it had come up had been on graduation day with her teasing me about how it never happened, and how that was too bad for me since the deal was now over. I figured that I had nothing to lose with my parents gone for more than 24 hours, so I called her up and told her that this was the chance for us to finally make good on our deal, assuming she wasn’t just bluffing for all those years. She wasn’t.
She lied to her folks, telling them that she was going to sleep over at a friend’s house, and she drove to my house and parked her car one street over just to be sure that no neighbors would see a car in the driveway and mention it to my parents. She was incredibly flirty, and we were both turned on by the “naughty” aspect of the fact that we probably shouldn’t be doing this since our parents were all pretty straight-laced, but we were doing it anyway and there was a small risk of getting caught.
I wanted to impress her, so as we talked about high school memories and looked ahead to college, we did all that talking in the kitchen while I cooked dinner. I have always had a knack for cooking, and she kept complimenting me on my skills as I made a (in retrospect relatively simple) dinner. But she watched me put the whole thing together from scratch, and helped out with some of the preparation, which made it feel a bit like a date. Since we were already breaking some rules, we pushed it even further, and when we sat down to eat I took a bottle of wine from my parent’s wine rack, on the (correct) assumption that they would never notice it missing and just assume that they’d drank it. So we drank a bottle of wine with dinner, us two 18 year olds, and that had us sufficiently buzzed for our game of strip poker, which we played in my bedroom.
Through the luck of the game, we ended up in a situation where I was in my boxer shorts and she was in her bra and panties. And she’d dressed knowing that I would probably see her this way, wearing a cute-more-than-sexy bra and boy shorts. We agreed that we’d allow the other person to do a dare in place of removing one of the “critical” pieces of clothing.
One hand ended in a tie, and she dared us both to have another bottle of wine. I was nervous that a second bottle might be noticed, but my parents had an open bottle of vodka in the freezer, so I suggested changing the dare to us both doing a shot of vodka. We did that, and that really had our inhibitions lowered. I still remember standing in the kitchen with this girl, with the lights off except for the light from the freezer, watching her throw back a shot of vodka in just her underwear and seeing her nipples poking through her bra a bit due to the cold from the freezer. I remember her watching me do my shot while moving her eyes from my face to the obvious erection in my boxers, then meeting my gaze with lust in her eyes.
I lost a hand and she asked me if I owned any briefs. I did, and she dared me to change into them from my boxers while facing away from her. I did, and she commented on my butt as I did so. Of course, then I had to turn back around to play the next hand, and my cock was barely concealed at this point, given the underwear I had on and how hard I was.
She lost a hand, and I dared her to kiss me, which led to a few minutes of making out with our bodies pushed up against each other. She lost another hand, and without hesitation reached behind her back and undid her bra, giving me my first look at her perky B-cup breasts.
I lost a hand, and told her that I was willing to remove my underwear unless she didn’t want me to. She didn’t stop me, and I still remember feeling my cock twitch as I stood there watching her stare at my exposed erection.
She declared victory and then asked me how far I was hoping to go tonight, saying up front that she didn’t want to have sex. I told her that was fine, but that I was hoping to win another hand because there was still one part of her in particular that I wanted to see and to kiss. She kind of got shy at the suggestion of oral, and asked if I’d ever done it before. I said yes, and she said the name of my ex-girlfriend (from the previous section) in a question-like way. I nodded. She asked me if I liked doing it. I said that I loved it, and that there was a reason why I shaved while she was on her way over. She said she’d never had that done to her before and was nervous, but that she’d let me kiss her over her underwear. So we did that. We made out. I enjoyed her breasts and nipples. I ravished her inner legs and thighs and basically french kissed her pussy with her soaked panties the only barrier between her pussy and my tongue. She was loving it all, rubbing my cock and jacking me off while I was pleasuring her. Eventually she pulled me up and we made out more, with her kissing her own juices off of my face. She pulled off her underwear and guided a finger into her pussy and after some attention to her breasts as well, it was obvious that she had an orgasm.
I was still hard as an iron bar, and we were both really sweaty. She said she wanted to go down on me too, but that she didn’t want to swallow anything. Her next actions suggested that this was probably not the first time she’d done it. She led me down the hall to the bathroom, had me stand against the wall, opened the toilet, and put the bathmat down in front of me. Then she gave me a sexy look as she got down on her knees. I’d been close to my breaking point for a while, so it was probably less than a minute before I gave her the warning and unloaded into her mouth, and then watched her turn around and spit into the toilet.
The next morning was a bit awkward. We were friends who had just taken things to a big new level, but we were about to go to different colleges. She made a point of saying that she only wanted to be friends, and that she didn’t want last night to “mean anything”. I was fine with that too, and glad she was the one saying it and not me. We parted on friendly terms and years later shared a private laugh remembering that night while at a high school reunion.
** THREE **
It was a while until another girl stayed overnight in this house — not until a college girlfriend came down to visit for a few days between Christmas and New Year’s.
This girl had a bit of a crazy streak in her, in that she didn’t particularly get along with her parents and she always had kind of a weird tension with my mom. She acted out on this weird parental dynamic in ways that were good for me sexually, so I went along with it.
For example, the first time I was set to meet her parents was when they were in town visiting her at college and we were all meeting at a restaurant. Just before we went to dinner that night, she sucked me off in her dorm room and swallowed my load, and then left for dinner only taking a sip of water. She said she wanted me to meet her parents knowing that my cum was in her belly and that she had cum on her breath. That’s pretty messed up in retrospect, but I went along with it because I was in college and it was a blowjob.
Back to the time of her visiting for New Year’s, she had a similar thing going on. But by this time we were further along in our relationship sexually — she was on the pill and we’d stopped using condoms. Each night of the trip, she had me come to her in the guest room — just like I had with my girlfriend in the first story — only this time we fucked and she got off on the idea of walking around my parents’ house knowing that she had their son’s cum inside of her pussy.
** FOUR **
Another break of multiple years and multiple girlfriends, until it was my dad’s 60th birthday party and I brought my girlfriend home with me for the few days that we were going to be there. She’d met my parents before and they all really got along well. But unlike 10 years previous at the beginning of this story, we were allowed to drink as much as we wanted.
By late that night, we were both a bit drunk and very eager for each other. Meanwhile, I was very cognizant of what had happened exactly 10 years previously, which made me extra turned-on, even though my now-girlfriend didn’t know that story.
When I came to her room after everyone had gone to sleep, she was exceedingly worried about us making any noise at all and getting us embarrassed by my parents. We were only doing oral sex at this point in our relationship. She held a pillow over her mouth while I ate her trimmed pussy to an orgasm. When it was my turn, she whispered in my ear, insisting that I had to remain completely silent, not even making noise to give her a warning when I was close. So exactly 10 years after the first part of this story, I found myself once again on my back on the same bed, in exactly the same spot. 10 years prior was the first time a girl made me cum, and now 10 years later a different girlfriend was gagging a bit on my cock as she swallowed my load with no advance warning. She commented afterward that I felt extra hard and seemed like I had cum more than usual. She was right, but I never told her why.
Source: reddit.com/r/gonewildstories/comments/964bvs/four_memories_of_fooling_around_in_my_parents
Great memories… I personally love and miss the innocence of girl #1 and the sexual appetite of girl #3