Mine was when I was 21. It was my first ever 'weird' sexual experience (Which is weird in itself since this was 1977!) and also probably my luckiest ever escape from big trouble.
EDIT:
I had originally intended to just set out the facts, but as the memory flooded back, it ended up a full length retelling. If it's too long it can be moved to true sex stories.
END EDIT
I had flown out from the UK to Norfolk, VA to join a ship for my summer sea experience cruise between graduating University and starting at the Royal Naval College. I was staying in a nice hotel downtown while waiting for my ship to arrive, and was flirting with the waitress over dinner. I had asked her for advice as to a good night spot, since it was a Saturday, and she suggested she take me to a country music club down near the beach. She was called Jenn, she was divorced and quite a few years older than me but pretty good looking so I was glad to agree.
We closed the place down, had breakfast and then went back to her place - a beach-front trailer park - around 3am. We did the nasty for a while then went to sleep. Her alarm went off at 5:30 and she tells me she has a 6am breakfast shift at a local diner. She wanted a morning 'quickie' first though, so we got started on that. She was on top of me riding me hard when the bedroom door opened, and a teenaged girl walks in! "Oh, sorry, Mom," the girl says, "Didn't know you had company. I was just checking you were awake as I heard you come in late." Jenn didn't stop - Hell, she didn't even slow down!
The girl walked over to the side of the bed and looks at us both, which freaked me out but didn't seem to faze Jenn at all. "Coffee's brewing," she says to her Mom, and looks me full in the face. "What about you? Coffee?" I sort of stammered a "Yes" of some sort, and she turned and walked out. "Well," I thought, "That was odd," but we were alone again, so I just let Jenn carry on bouncing up and down on my cock.
Not more than two or three minutes later, to my shock, the bedroom door opens again and the girl walks back in with two cups of coffee which she puts on the nightstand right next to me! To say I was gobsmacked would be the understatement of the year. "Thanks, Jessie," Jenn grunted, continuing to ride me as her daughter stands there watching. "You did good, Mom," she said with a giggle. "He's hot!" Jenn didn't answer, and it seemed to me she was getting close to cumming. I felt I should toss her off me and cover up, but it was also a turn on, this pretty hot MILF riding my cock to her cum while her cute daughter stood and watched.
Jess was eighteen, wearing an oversized white t-shirt, and as she watched us she reached down, grabbed the hem, and pulled it up over her head. She was wearing nothing under it, and I was treated to a lovely pair of pert 'A' or nearly 'B' boobs with hard little nipples sticking out of pale pink areola, a smooth firm flat expanse of toned tummy, and a sweet little puffy pussy with a light dusting of fine blonde hair.
Jenn's moaning was getting faster and more insistent, but she said nothing at all as Jess stepped up onto the bed, straddled my head, and lowered her pussy right onto my mouth, kneeling on my arms as she did so. Well, with her trapping my head and arms, and her Mom riding my hips, there wasn't much I could do if I had wanted to, so I just went with the flow and started eating that delectable little snack. She leant forward, rested her arms on the headboard, and began her own moaning as I licked her clit and pussy.
In mere moments after I started eating Jess, Jenn started gasping "Yes, yes, here I cum, yes, yes...." and had a shuddering orgasm on my cock. I didn't cum myself, but kept eating Jess, even when Jenn got off me and I heard her walk into the bathroom. I heard water running and splashing, and then Jenn come back out into the bedroom, and the sound of drawers and such, but she didn't say anything, and I couldn't see anything with Jess sitting on my face.
After a short while, I heard Jenn say "OK. I have to go to work. You guys have fun." Jess sat up straight, and I could see her Mom standing right next to me by the bed in an IHOP uniform. She blew me a kiss, kissed Jess on the cheek, and left. I was in utter disbelief. She was leaving me in her bed, eating her daughter, less than 12 hours after we'd met! Jess didn't even seem to find it strange, though. She raised off my face, turned, and dropped her pussy back onto my mouth and her face onto my still fully erect cock.
The girl was an expert cocksucker! I ate her to several cums as she sucked me close to the edge again and again, never quite bringing me over the brink. Finally as she had another massive orgasm of her own, I could take no more. I grabbed her head in both hands and fucked her face hard and fast till I came in her mouth. She gulped it all down, and I rolled her off me to lie next to me as we both got our breath back. She closed her eyes, and I sat up and stepped off the bed to go to the bathroom.
She grabbed my wrist as I tried to leave, pulling me back to the bed. "No, come back, I want more!" she said. "I need to pee!" I replied with a grin, pulling her hand off my wrist. I went into the bathroom and used the toilet. I stood there looking in the mirror as I washed my hands. This whole situation was really weird. I decided I'd better have a quick shower and leave, and to heck with the little sexpot.
I started the shower, but no sooner had I got in than the curtain slid back and she stepped in next to me. "Mmmmm," she whispered, rubbing her face against my chest. Her hands reached behind me to play with my butt, her lovely firm little titties pressing into my tummy. Good intentions or not, almost instantly my cock started growing, and she giggled. She grabbed a 'soap on a rope' and started lathering us both up. By the time we were both clean and rinsed I was as hard as marble, and she used my cock as a handle to lead me back to the bed. She pushed me onto my back on the bed, then reached into the drawer of the nightstand to pull out a condom. She used her mouth to put it on me - which was the first time I'd actually seen that trick - then carried on blowing me as she again lowered her pussy onto my face.
This time, though, as I detected her approaching orgasm, she stopped, got off me and slid down to my cock. Kneeling over my hips she held my cock in one hand, her lips open with the other, and lowered herself down onto my shaft. I slid all the way up into her, although GOD but she was tight! She went to work like an expert, alternating sliding up and down on my cock with rocking back and forward to rub her pubic bone on mine. Just as when she'd been sucking me she was a total expert. She had cum after cum, while skillfully keeping me from my own, but hovering on the edge. At last though, like before, I could take no more - I was only 21, after all, even if that did make me the senior partner!
I grabbed her and rolled her over onto her back. I took a firm grip of her legs and lifted them up and apart and began just pounding her into the mattress. I swear the whole trailer was shaking when, in a very short time, I erupted into her with a moan and a cry as she too cried out and came.
I collapsed on top of her, gasping for breath as she did the same under me. When I could breathe I rolled to the side and removed the condom, wiping myself with her discarded t-shirt. I sat up and drew a deep breath. After two orgasms the rational part of my brain was starting to make itself heard. "If it seems to good to be true, it is too good to be true!" kept running through my head.
"That was amazing, Jess," I told her, "but I have to leave. I have to report to base." (I didn't until Monday, but it was an excuse.) "No, please," she begged, "don't go! That was the best sex I ever had, I want to do it again!" "Sorry," I replied. "I really have to go." She sat up and put her hand on my cock. "I bet I can make him change his mind," she said with a grin... "And we haven't even done anal yet!" My cock twitched as I heard that, but again, in my mind, "If it seems to good to be true, it is too good to be true!"
How about tonight?" I asked her. "I'll be free again this evening." I could swear that the look that crossed her face for a second was relief, which seemed odd to me. "OK!" she exclaimed happily. "My Mom can pick you up at your hotel again!" She buzzed happily around me as I dressed and headed for the door. She followed me, slipping the t-shirt back over her head, despite the cum stains down the front. I opened the front door into the light of dawn to see a pretty busy scene. There were two or three police cars and a tow truck in the parking lot, all with their lights flashing, and several people standing on the porches of their trailers watching a beat-up old Dodge being winched onto the tow truck.
One older lady saw us step out and hurried over. "Jessie, dear, oh, it's terrible, are you going to be alright?" She looked at me, and at Jessie in what was obviously her nightwear, and pursed her lips. "Hello," she said to me. "Are you a friend of Jessie's?" "No," I replied, "of her Mom," as Jessie spoke over me "What's 'terrible', Mrs. James?" "Why, Jessie, dear, your father! The police car followed him into the park, pulled him over and did a sobriety test, and they've arrested him!"
I looked at Jessie and she flushed with the guiltiest look I've ever seen. So THAT was why she'd done so much to make the sex last as long as possible and to keep me there for another go-around after each time we finished. She was waiting for her father to "catch me" with his daughter. The old badger game, though with a twist of Mom doing the pick-up then leaving me to be caught with the daughter. Being a 21 year old foreigner staying in an expensive hotel, Jen must have tagged me for a good mark for blackmail.
A lucky escape...... but man that girl could fuck! 40 years later I still remember her.
*edited for age