Two Boys Wild Night with Rose

This story may read like a fantasy, but the basic facts are 100% true. I’ve just added some dialogue to give the full flavor of what happened. It happened many years ago, but I’ve never forgotten. And, I kept a journal at the time, so I wrote it down within days. I still get excited thinking about it, and it is arousing to be writing it down to share now.

My friend Jack and I were just 19, sophomores in college. We’d decided on the spur of the moment to hitch hike down to Florida from Boston for spring break, which was not yet a commercial media event. Final exams were after Christmas vacation then, followed by spring break (no capital letters!). Jack and I left Boston headed for Florida to catch some sun, drink some beer and chase girls. Looking back, we were incredibly inexperienced sexually. I’d had intercourse with just 2 girls, 5 times total. Jack had never gotten laid. Most of our so-called experience consisted of rushed hand jobs provided by girls who sympathized with our plight, “blue balls”. We were hoping to change all of this in Florida. At that age we were very, very horny, all of the time.

We arrived after just 6 rides at Daytona Beach, still well north of our destination of Fort Lauderdale. The trip took us 32 hours, with about 5 spent sleeping in a motel in North Carolina.

We were elated, but exhausted as we walked into a burger place (White Tower, I think), trying to figure out what our next move was. It was about 5PM. We asked the waitress and she told us that the beach was still about 4 miles away. We ordered burgers and coffee and contemplated going back out to catch one more ride.

That’s when Rose approached us. Rose was older, maybe 38 or even 40, but she was very attractive, “hot” unlike the girls or women we saw in the north back then. About 5’5”, she was slim and compact in very tight jeans that showed off a perfect round ass, slim hips and a very narrow waist. Her hair was platinum, with a pinkish tint! Her great big eyes were a brilliant blue. She wore lots of eye makeup, bright red lipstick: kind of a “Dolly Parton look” without the oversized boobs. She was however showing a lot of cleavage, her cowboy shirt (complete with ”Rose” embroidered over her left breast) open by 2 or 3 buttons.

“How y’all doin’” she asked us with a great big smile, in the thickest southern accent imaginable.

The brief conversation that ensued established the fact that we’d thumbed down from Boston, that we needed a ride out to the beach, and that we had no plans on where we would be staying in Daytona. And that Rose was from Nashville, was down for the car races, and was amazed that we had no idea where we’d be staying. With the races and all the “college kids” in town, most places were booked solid, she informed us. She offered us a ride as she was heading out to the beach. Walking out of the burger place and across the lot, we noted that Rose was well-known, greeted by name by several men and women as we left. She sure was friendly!

Her car was as hot as she was, a bright red Pontiac GTO convertible, top down. She explained that she was in the car race business and asked us about our backgrounds, what we were studying, and so forth. This was almost unbelievable to us and we wondered what would happen, me sitting up front, eying Rose, sneaking glances back to Jack as she drove. We were loving the warm, soft Florida air. Rose talked about a couple of places we might get rooms. Then, just after we got to the beach, she pulled into a very fancy beachfront motel. I said that we didn’t have much money, so didn’t want to pay much for a room, adding that we could even sleep on the beach. Rose just laughed in her open, kind of loud way and told us not to worry, this was her place and she was just stopping to use the phone to call around for us. Talk about Southern Hospitality!

She invited us up to her room, on the top of 4 floors. It was awesome, with two large beds, one whole wall glass with sliding doors opening onto a small porch, overlooking the ocean through palm trees. Palm trees! We were psyched. This was definitely not Boston.

Rose offered us beers, which we eagerly accepted, and went to the phone while we stood out on the porch enjoying the warm late afternoon air and blue ocean. We talked about Rose now that we were out of earshot, agreeing that she was amazing, really sexy in spite of her age and really, really friendly. We wondered if something was “up”, and decided not to worry about it. After about 5 minutes she came out.

“Well fellas, I think I found you a place. Only trouble is, they have no rooms until tomorrow. But let me ask you something. I hope you don’t take this wrong. You’re a couple of nice lookin’ boys, and you seem real nice too. I could let you stay here tonight with me if you want to.”

Jack and I were speechless for a minute. Finally I stammered “that would be great, why not, yes, yes, we’d love to”. I could not really believe what I’d just heard from Rose. I felt my ever-randy penis start to swell. Jack looked uncomfortable and remained speechless. We got our backpacks from the car and brought them to the room, nervous, wondering if this was real and if it was safe. This kind of thing just did not happen at least to us.

We sat out on the porch, talking, having a few beers. Rose offered us a joint that she produced from a pack of Luckies. We passed it around and soon started to feel nice and stoned, loosening up and laughing, mostly at her jokes and stories about life on the car race circuit. We had some Chinese food delivered and ate it eagerly. At about 8:30 P.M., Rose asked us: “So do you boys boys mind if I change into something ‘a little more comfortable’ as they say?”

At that Rose got up and went into the bathroom. Jack and I sat and sipped beers together, very quiet now. Then the door opened and in walked Rose. I am certain Jack’s and my mouth literally fell open. She was wearing a see-through pink baby doll negligee with tiny bikini panties, also see-through. What a great body! And for a not-tall woman she had very long shapely legs. She stood before us and posed like a runway model, half turning to display herself. She sat on the edge of one of the beds and said: “What are y’all waiting for? Get over here, right now.”

Jack and I stood up and walked over to her. Rose took charge completely. Her tone changed a bit, as she now gave the orders to us neophytes.

“Well, let’s go boys, let me see what you’ve got there. Get those clothes off! “

We removed our shirts, then our sneakers, socks, and finally our jeans. Rose looked as us for a moment, standing in our white briefs both feeling embarrassed and overwhelmed by the situation. “Hmm, pretty nice. Love those young bodies. Let’s go, get those off. I want to see those cocks of yours.”

We dropped our underwear and stepped out of them. My uncircumcised penis had been hard earlier, but as the moment of truth approached had shrunk. Now it was just slightly semi-hard, the head protruding partially from the foreskin. Jack’s very thick, short, circumcised penis was soft,, but the head was very fat and glistening. Obviously he’d been aroused too.

“Well, well, let’s do something about those poor little cocks. Jack, you come over here.”

With that Jack moved directly in front of Rose and she proceeded to take him into her mouth, her lips surrounding the shaft, then moving up and partially over the head before going down again. One hand went to cradle his big balls, which hung pendulous in their sac. Her attention had instantaneous effect on Jack. He grew in her mouth, stiffening with each up and down movement of her mouth. After no more than 20 seconds Rose withdrew her mouth. His now-raging hard-on was even thicker and the head fatter than before, definitely much more “big fat” than “big long”, it stood out perpendicular to his torso when she released it and turned to me. I realized that I hadn’t seen an erect dick except mine since I was maybe 13 and my friends and I did a little “social masturbating”. But this was very different.

My cock had stiffened just from watching them. By the time Rose took me in her hands then her mouth, I was almost at full erection, which was over 7 ½ inches, a couple of inches longer, but much thinner than Jack’s. She made “mmmm” sounds and slurped as she worked my cock in her mouth, running her tongue around the sensitive tip. I’d never experienced oral before. In another half minute I’d have cum.

But Rose left, slipping her mouth off my cock, which was so aroused that it bounced uo almost to my belly, pointing up toward the ceiling. “Real nice cocks you boys have there. I love ‘em young, big and hard. This is goin’ to be a real fine time, you just wait. Now just do exactly as I tell you, ya hear?”

With that she told us to join her on the bed and told us to play with her a little. We fell to her, one on either side, fondling her perfect medium-sized breasts under her nightie. I kissed her sensuous wide mouth deeply with my tongue and she responded in kind, driving me wild. She raised her bum so we could remove her panties. Our eager hands roamed all over her supple body and she responded by making herself available to us, spreading her legs wide, thrusting her chest up to our mouths which began to work her now-erect nipples. My hand met Jack’s at her pussy, both of us stroking her labia, feeling her oozing wetness. I entered her with my middle finger, marveling at how warm, wet and silky smooth she felt.

Rose began to respond with pure lust, telling us: “Feel my hot cunt! You like my hot cunt? Suck those nipples! Suck them hard!” She was writhing on the bed between us. Then she turned away from me, my finger still probing her hot pussy. She pushed Jack back onto the bed and went down to his crotch with her head. She cooed: “Ooooh. What a nice big fat cock you have! I’m going to suck it now. You want me to suck your fat dick, don’t you Jack? You want that, don’t you? Tell me you want me to suck you. Tell me!”

Jack said in a breathless whisper: “Oh yes, I do. Suck it, please.”

With that Rose plunged her mouth over his immense cockhead. I could see her lips being stretched to accommodate his girth, but she took it all in and began to slide down and up his pulsing shaft, almost to the base. He lasted no more than a minute, shouting “Oh god, I’m cumming! Shit! I’m cumming now Rose!”

Undeterred, she kept sucking, moving up to concentrate on his glans squeezing his shaft and balls as he raised his hips and shot stream after stream into her eager mouth. She swallowed as much as she could, the rest dripping down from her lips onto her chin. This was unbelievable! Neither of us had ever gotten a blow job before, and here Jack was cumming in a beautiful woman’s mouth right in front of me. And we’d just met her a few hours before.

Rose continued: “Now I need penis in my pussy. I need to get fucked, you hear me, Joe? She kissed me hard on the mouth, plastering her wonderful body against me. My erection was up against her thigh just above one knee as I was probably 10 inches taller than her. She felt so good! She rolled on top of me, sitting facing me, an threw off her nightie. She grabbed my pole and lowered herself, guiding it into her wet pussy. Then it was in, oh yes, it was in. I arched my hips, driving it further. She was warm, wet and her pussy felt like it was sucking my cock.

“Oh…oh it’s big. I feel it in me. It’s so good, so big and so hard. Don’t move yet, just you wait, let me sit down on it. Ahh, that’s good. Your cock, I love it, I love it fucking me. Oh yes, fuck , fuck me now.”

It was too much. I felt my rising throbbing pleasure growing. I tried my best to hold off. Then Rose began to ride me, up and down, slowly, sensuously, telling me yes, she wanted me fuck her with my big prick. In a moment I lost it. Gasping for air, my entire body electric, stiffening and convulsing in pleasure I shot a huge load into her, spurting over and over. It was like nothing I’d ever felt before.

Rose was in heat! Jack and I had both cum but she was just getting started. She’d rolled off my diminishing dick and was back at Jack, rubbing against him, kissing him on the mouth, humping against him, handling his cock and balls. She got him hard again within minutes! Now Rose lay back on the bed, pulling Jack onto her. He was about to have his very first fuck, and what a fuck it would be. Rose spread her legs wide underneath him, bending her knees on either side of him. She reached down and brought his manhood to her pussy lips. She rubbed him up and down her vulva, using his massive tool to stimulate herself. Then slowly, she stuffed him into her. “Whoa, you sure got a big cock Jack. Take it easy with that thing or you’ll tear me up, hear? Jack was in ecstasy as she took him inch by inch until he was buried to the hilt. She made him stop and rest it all the way in her, savoring him. Telling us how full of cock she felt. I felt my own member begin to thicken and rise again.

Rose called all of the shots, telling Jack exactly what she wanted him to do, telling him to slow down, to stop, and to fuck her hard, letting out little noises “uh, unh, uh, ooh, ahh, uh, uh…yes, yes, good, fuck…” Jack had some staying power now, having just had an orgasm not 15 minutes earlier, but he was getting more and more aroused too, grunting and moaning as she guided him in his first fuck. Rose was getting close.

“Ohhhhh, yes, yes, oh god yes, can you feel me Jack, can you feel me getting wetter, getting wetter on your big cock? I’m, I’m gonna cum Jack. Cumming. Fuck me! Cum with me now. I want to feel you cum with me, cum deep inside me. Cum now!”

She pounded his back and slapped his ass as her orgasm overwhelmed her, bringing him off with her. Jack fucked her in a frenzy, pounding her hard, her legs wrapped around his waist as his balls slapped into her ass, which was raised to meet his thrusts. He grunted hard as he let fly his second huge orgasm, deep in Rose’s pussy.

All four of us rested for a few moments, sipping on some cold beers. Rose lit another joint and passed it around. “This is great,” she said. “Oh yeah” we agreed.

Rose was tireless. Now I wanted to go slow, to enjoy her hot body. I began to caress her breasts and firm ass. Jack’s and my cum ran out of her pussy down her crack. She fondled me, remarking again on my size, marveling at how us young boys “could be ready to go again so fast”. I kissed my way down her chest and belly, wanting to go further, something else I’d never done before. I hesitated. Rose encouraged me, guiding my head further down to her soaking pussy. I eagerly complied, tasting my first pussy, with the saltier taste of our cum mixed in. She was delicious, like sweet honey. I licked her in and out and all around, letting her guide me to where she liked it the most. Once I looked up. Rose had Jack’s cock back in her mouth!

I tasted a slight change as her orgasm approached and was eager to finish, but Rose had other ideas. She got onto her hands and knees on the bed, her ass and pussy facing me. She told me to give her my cock. I stood on the floor behind her and she guided my cock in into her soaking pussy. She positioned Jack lying in front of her so she could suck his dick while I pounded her from behind. Now I too had some staying power, and hoped to satisfy her as Jack had. As our arousal was growing, she stopped sucking Jack and told me to stop. “I want you both” she said.

Rose reached across to the bed stand and took out some KY Jelly, handing me the tube. “I want you in my ass, Joe, while Jack is in my cunt. I always wanted to do this and you two are gonna do it.”

She directed Jack to slide over, to lie beneath her, his legs hanging off the bed between mine while she straddled him. My cock had slipped out of her and stood erect, just touching her ass crack, waiting for the next moves, admiring her perfect ass, holding one cheek in each hand. Rose leaned forward to Jack’s chest, really exposing her pussy and asshole to me. She reached for Jack’s erection and held it while she slipped down onto it. I marveled at how easily she could take it now that she was totally aroused. She leaned way forward, careful not to go so far as to make him slip out. She told me to get ready. I took a glob of KY and smeared it over my penis then onto her asshole.

“Good, Joe. Now put it into me. Go easy, slow.” I pushed my glans against her tight anus. Easy, easy, very easy… wait now, push a little, not too fast, be careful. Go slow.” I pushed some more, felt her sphincter resist, then suddenly relax to let my well-lubed cockhead slip past and into her asshole. I was there! What a feeling! It was truly beyond my wildest dreams.

“Wait now.. hold still. Hold still for a minute. Both of you. Don’t move. All right now move. Move just a little. That’s it, move together. One in while the other is out. Can you feel your prick against his? Oh yes, go a little harder, like that. Yes, yes, your cocks are in my ass, in my cunt, fucking me. Can you feel him, feel your cocks together? Filling me up with your cocks, so big, nice. Further in my ass Joe. Go further up my ass now. Give it all to me.”

I pushed all the way to the hilt. Rose instructed Jack to push all the way in too, moaning loudly as he did so, then she ordered us to stop. Our balls were actually touching. I could feel his prick distinctly through the thin wall separating it from mine. As Jack began to move again, at Rose’s command, I could feel the bulge of his cockhead rubbing up and down my still motionless shaft. Whoa! That felt too good. Then Rose told us to fuck her good. We let loose, sometimes both way in sometimes both almost out. Rose screamed and cursed and I felt our balls collide when we were both buried to the hilt. Rose went nuts. So did we.

Jack came first. I felt his dick throb and pulse, over and over against mine as he shot his third load of cum into her. His spasms sent Rose over the top again, and she screamed and moaned as her orgasm swept over her. Her asshole began to spasm wildly as she came, and that triggered me to cum hard, my knees buckling as I kept pounding her ass and cumming, cumming, and cumming. My ejaculation into her tight ass in turn set her off into another orgasm even before her first had fully ended. She just swept back into a crescendo of screams her body quaking, her sphincter squeezing, milking ever drop of cum from my erupting dick, my orgasm sweeping over me from toe to head and back. As my cock softened and popped out, followed by a stream of cum, I looked over at the clock next to the bed. It was just 9:20, less than an hour after we’d started. Between the 3 of us we’d had 8 orgasms already!

Jack and I were pure testosterone in those days, and recovered soon to do it again and again. Doing things we’d never done before wasn’t much, because we’d done so little before. But we did things that night that I’ve never done again, including the three-way just described, which we repeated toward dawn, only with Jack (amazingly and with great care) in her rear, me in Rose’s pussy. Rose was tireless, keeping up with two extremely horny boys maybe less than half her age, which we never found out. I lost track of her orgasms and Jack’s (he told me later he’d cum 7 times) but I know I came 8 times including two after we woke up at noon the next day. We must have taken 4 or 5 baths each , Rose maybe even more.

The following afternoon, Rose drove us to a small motel that was more in the “Spring Break” area. She got the key herself, leaving us in the car as she did so. She went into our room with us, and we assured her it was fine, small but right on the beach at ground level. She told us she’d had the night of her life with us, that sometimes she just needed to “get my brains fucked out” and that we’d done just that. She said she’d be feeling us in her pussy and ass for days, but that it was a “good sore feeling” that she’d remember us by. She added that if Tony, the owner of this motel asked us, we were to tell him that we were “baseball players from Nashville, friends of Rose’s from up there.” We thanked her for everything, wishing she’d stay, certain she’d return. Rose walked away, her perfect ass swaying in her skin tight jeans, waved as she got into her car, and drove off.