Okay so this is a throwaway account because if this got out in my friend group he would be screwed. For reference this kind of happened over 3 non consecutive day as i get fucked by this guy twice. This is his first time fucking me, if y’all like this I’ll post that other time too. Also something you need to know about me, I’m very dense so it’s hard for me to realize someone has interest in me and I’m usually too shy to go right out and ask someone to fuck me.
So it started out as a friends night the first night, the guy had been going through a rough time after a messy break up and I was hanging out with him more often to cheer him up. Were hanging out in his apartment watching Stranger Things and we ended up having a tickle fight. This guy is a good bit bigger than me so I do not do a lot of winning in this tickle fight. (I’m curvy at 5’8″ while he’s husky at I would think 6’2″)
The thing is while he’s somewhat ticklish I’m only ticklish one my inner thighs and arm pits. My inner thighs are also a place that turns me on a lot.
He figures out that I’m ticklish there rather quickly due to my very short shorts and starts putting his hands there a lot. He goes up and down my thighs while I’m squirming underneath him on his couch, laughing and trying not to show that I’m turned on.
I squirm out from under him and fall to the ground because I had found out earlier that his feet were ticklish, my ass in the air in front of him, and looking extra fine due to my thong. I can see him trying not to laugh as i spot a rather large bulge in his pants.
He pins me down again, his hands going higher and higher to the point his fingers are brushing up against the ends of my shorts. It takes all my will power not to moan as my thong got wetter and wetter.
All this goes on for a while, but this night due to me wanting to go to a sleepover and being a derp thinking he wouldn’t want to do anything despite his boner i left, but not before setting up another hang out days later.
Skipping to this day I show up to his place and were hanging out when he mentioned he had to clean up some broken glass (another weird, less sexy story) in his bedroom and me being the somewhat nice person, i offered to help him clean up.
We get that done and I start another tickle fight, because I’m a glutton for punishment, and we end up wrestling on his bed, he easily pinning me down and feeling my legs, getting closer and closer to my sweet spot as I started to get wet.
At this point he starts to feel up shorts around my pussy, but never directly touching it, trying to fine other tickle spots around my hips. I squirm a lot, blushing and trying to twist around to my stomach with him on top of my legs.
When I finally turn over, he slaps my ass, hard, as I let out a moan. He continues to do that as we wrestle some more, his hands all over my body as I myself start to get more bold by pushing his head into my tits.
We both agree we like where this is going (more him making me say what i wanted because I’m very shy about sex) and i sit in his lap as we start to make out, him biting my lower lip and swirling his tongue around mine as his hand feel up my tits and ass through my clothes.
I start to grind my pussy against his cock as i break off the kiss to take my shirt and bra off. He’s immediately admiring my tits as i start to try to take his shirt off, but before I could he decides that he’s in charge and flips us over so that he’s on top again.
He then practically rips off my shorts and thong as his start to go to town, finally fingering my dripping wet pussy as i twist and moan under him, not use to someone knowing what there doing down there.
He kept moving between my clit and hole with his finger as he watched me cum twice before i got too sore (my clit is really sensitive and can get sore easily if handled roughly) and he started to eat me out.
His tongue swirled inside my as i wriggled on the bed in front of him, occasionally stopping and asking me if I liked being eaten out by a guy nearly a decade older than me, to which i whole heartedly said I did. I came another time from his mouth as i became a panting mess under him.
He then asked if i was ready for him to which i responded with a line about fucking me hard. He strips and he has the biggest cock I’ve ever seen outside of porn (I’d say roughly 8in and pretty thick) and folds my legs over my body as he enters me in one swift, hard motion.
His cock fills me up all that way as he holds me down and has his way with my pussy, fucking me hard and fast to the point of pain. He asked me if i liked getting fucked by an older guy and if I liked older guys. I moan out yes’s as i asked him how was my 18 year old pussy, to which he tells me I’m the tightest he’s ever had.
This goes on for a good 7 or 8 mins of jack hammering, missionary, and dirty talk until I tell him i wanted to top and give him a little break.
I start riding him slowly at first, his cock stretching my pussy and going deeper than i thought possible, as i rocked my hips back and forth. I loved seeing his face while I was doing this, his mouth wide open in pleasure as i swirled my hips in a slow fashion, pleasuring him but torturing him as the same time.
At some point he starts to get impatient and pulls me to his chest as he pounds me from underneath until i cum, his cock constantly hitting my g-spot. He wasn’t done though and kept fucking me until I felt his cock throbbing in me and him finishing in my pussy.
It was honestly the best sex I ever had and it’s had me craving for more, which i got, days later in what will be hopefully part 2. I hope you all enjoyed! ;)
Source: reddit.com/r/gonewildstories/comments/517xow/my_f18_first_time_with_an_older_guym27
Why would he be screwed? He’s single and you’re not a minor.
I really like having a relationship with a substantial age difference; the fact that society disapproves adds a frisson of excitement to it.
I met someone when I was in my late 30s, and she went on holiday with her parents just after New Year. I spent my first few days in work feeling cold and missing having my hands on her ass whilst she was rocking my cock, so I phoned up my stepmother (a travel agent) and the next day was off to the same town in Spain where she and her parents were staying in a villa. Didn’t realise my hotel was one street over and overlooked their villa. Surprised her in the street and spent the rest of the week avoiding her parents and sister (who actually caught a glimpse of us).
Very hot story! Bonus big cock haha :)
Mmm that was fucking hot… I can’t wait to read the next one… That guy sounds like a lucky guy…. I wish I had 18 year old friends like you ?