I was a latecomer to sex… I didn’t lose my virginity until I was 19, and after that I really didn’t have much sex or much interest in it until I started going out with my last boyfriend. He had a very high sex drive and we ended up fucking 3-4 times whenever he saw me, and was constantly talking about fantasies and ideas and things he wanted to do. As a result, I found that I really enjoyed just pure, simple sex, and so when we broke up a few weeks ago I soon realised I wanted more of it.
One thing we talked about but never arranged was him watching me with older men – I’ve always been into older guys (I’m 23, my ex was 30, and I lost my virginity to a 39 year old), and talking about that fantasy really turned me onto the idea.
This idea wouldn’t go away, and so a few days ago I signed up to a swingers site that my boyfriend had previously signed us up to but never went anywhere with. Once I’d registered and verified I got bombarded with messages… most of them rude, or impatient, or just dick pics, but I also heard from some interesting guys.
It was all very intense, but eventually I focused on one particular guy – he was 50 years old, wasn’t local but in town on business and staying in a hotel. He invited me to come by and see him, and the fact he wasn’t local and I could just meet him for an hour not too far from me made it an easy choice.
The following evening he messaged me when he was back at the hotel from work, and I took a walk to the hotel about 15 minutes from me. I’m 5 foot 3, very slim and petite, with red hair and 36C breasts. I wore a dress with a front zip and tights, over a bra and thong.
When I arrived at the hotel I messaged him to come down, and he appeared a couple of minutes later. He was 5 foot 9, slim, a little tanned, with a slightly goofy but charming smile and wearing glasses, and he came down wearing a black t-shirt and dark trousers, with a tattoo just showing on one arm below his shirt sleeve.
After introductions and a bit of talking, he asked if I wanted to come up to his room with him – I could already see a bit of a bulge in his trousers, and I was incredibly nervous but excited, so I said yes and we headed to the lift and into his room.
Standing in his hotel room, he came over to me and started running his hands over his body, then leaned in to kiss me, his tongue pushing into my mouth. His hands continued to roam over my body, before finding the zip at the front of my dress and breaking the kiss as he unzipped it fully before pushing it off my shoulders and letting it drop to the floor, leaving me in my underwear.
He told me I looked beautiful, and quickly pulled off his t-shirt, then his trousers and boxers, standing naked and erect in front of me in only a dark pair of socks. He kissed me again, pressing his body against mine, and letting me feel his hard cock, pressing against and then between my, legs as I shifted my stance. He moved his hips slowly, letting his cock press against my thong and slide back and forth while we carried on kissing, before he stopped and asked me to get on my knees for him.
I knew what he wanted of course, so knelt down and got a proper first look at his cock – it was the biggest I’d seen in person, a little bigger than my last boyfriend, and so I stroked it for a while in my small hand, with some precum already there to lubricate it, before shifting forward and taking some of it into my mouth. I sucked and bobbed my head as he gave out a long “fuuuck”, moaning and sighing as I sucked on him for a few minutes.
He then told me it was his turn and to get on the bed. As I lay down he ran his hands up my legs, getting to my was it and pulling down my tights while I lifted my hips to help him get them off. He then did the same with my thong while asking me to take off my bra, and I was soon naked. He took a moment to admire my body, before pushing my legs apart – his head was soon between them, and after commenting on how I was already wet he started to lick and suck on my pussy.
I can’t cum from oral, but I closed my eyes and enjoyed the sensation and it only turned me on more as he licked and sucked on my clit, clearly enjoying himself, making me sigh quietly and whimper a little.
Five minutes or so later he pulled away, climbing onto the bed and on top of me, between my parted legs. He asked me if I wanted him to fuck me, and I told him “yes please”. Sitting on his haunches, he took his stiff cock and spent some time rubbing it against my pussy, coating it with my wetness before very slowly, carefully easing it into me. I’m very tight, which he reminded me of several times as he eased into my inch by inch, sliding slowly out of me then a little further into me with each movement until he was fully inside me. Moving to lean over me and kissing occasionally, he started to thrust in and out, still slowly and quite gently, speeding up a little until he built up a steady rhythm. He moaned and gasped regularly as he fucked me, and I started to whimper with pleasure underneath him, while I could hear how wet I was with each thrust as he stimulated me.
Eventually he pulled away and told me to turn over onto all fours, before sliding more easily into me. He built up a steady rhythm again for a while, but eventually took a hold of my hips, pulling me back onto him as he began to fuck me hard. His body was slapping against mine and I was moaning louder as he pounded me.
After a while he pulled out of me and told me he wanted to see me on top, laying back on the bed as I straddled his erection, using a hand to guide it into me. After feeling him slide back into me, I started grinding my hips back on forth at him, enjoying the different stimulation before movin to start bouncing on him. We both clearly really enjoyed this feeling, and it only got better when he reached up to start massaging my boobs and sensitive nipples.
I lost track of things at this point as I felt myself getting closer to cumming, so I just remember bouncing hard on him and finding just the right angle to get off, and hearing him telling me to “cum on his old cock” as I moaned and whimpered before moaning really loudly as my orgasm hit me.
He gave me a little time to recover before rolling me over onto my back so he was on top of me again. I was really wet now, and he was fucking me hard, watching my expression as I lay under him with legs spread. He was talking more now, about how tight I was, how good my pussy felt, and how he was going to cum deep inside my tight young pussy. He fucked my hard, his cock moving in deep, fast, thrusts, both of moaning until he finally couldn’t take any more and he buried himself deep inside me while grunting and crying out loudly on top of me while he came.
He stayed like that for a while until finally pulling out and rolling off. He talked some more about how good it was, and I told him how much I’d enjoyed it, before he offered to let me use his shower. I was planning to head straight home but decided to at least wash off before dressing again and saying my goodbye, still feeling satisfied.
I have no idea if this guy will be back in town, but I’m already keen to plan more meetings with older guys!
Source: reddit.com/r/gonewildstories/comments/nw3rk9/meeting_an_older_guy_from_a_swinging_web_site_fm