Riley's Awakening
Copyright© 2025 by Vanpeebles
Chapter 4: Threesomes & Sugar Daddies
Coming of Age Sex Story: Chapter 4: Threesomes & Sugar Daddies - A story of a young woman's exploration of her sexuality and discovery of her attraction to older men. The incest is only in the first chapter, so you can skip that if you prefer.
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa Ma/ft Fa/Fa Consensual Lesbian Heterosexual Fiction Incest Father Daughter Group Sex Orgy Anal Sex Analingus Cream Pie First Masturbation Oral Sex Sex Toys Teacher/Student
The lockdown finally ended, and the city started opening back up. Sex with Puck had been fun, but I really missed a good, hard cock inside me. The strap-on was just not the same as musky, male flesh. So when Puck suggested, once again, that we should go out and pick up some guys, I finally said yes.
I thought we were going to hit some clubs, but Puck said that clubs were great for dancing and drinking and maybe going home with a guy, the chances of bringing home an asshole were high. It was impossible to have a conversation and screen a guy in a club. Instead, she knew a few good upscale bars that were better. For one thing, you could go out before ten and be home and fucking at a decent hour. For another, the guys skewed a bit older and were more mature and experienced. She gave me a wink as she said that last.
We sat down at the bar, and it wasn’t more than five minutes before a guy had come over, bought us a round of drinks, and was chatting Puck up. He was in his mid-twenties and cute. He started talking about himself, and I quickly lost interest and didn’t pay much attention to what he was saying after that. Puck seemed engrossed though; I couldn’t tell if she really was or if it was just an act. Puck was good at feigning interest in something, and if she thought a guy might be a good fuck, she could tolerate a lot. I’m not like that. I like to fuck, but I have to at least like the person.
I had decided to be more outgoing and to try to catch the eye of some attractive guy. That’s when I spotted Billy. He was tall, over six feet, broad chested, and ruggedly handsome. He looked to be in his mid-thirties. I stared at him for about a minute, and when he glanced my way, I smiled at him. He made his way over to me and introduced himself.
He was a lawyer, single, and I liked him from the start. After the obligatory “aren’t you glad the lockdown is over” conversation, he started asking questions about me and seemed genuinely interested. We were soon talking about all sorts of things. His interests were broad, and he was well read. I was starting to really like him.
Then I heard Puck say, “Take your hand off me.”
Evidently the guy had started to get handsy. Puck had brushed his hand away, but he persisted.
“Aw, come on,” he said. “Let’s have some fun.”
He was obviously drunk and put his hands on her again.
Then Billy stepped in, “Leave the lady, alone.” He towered over the other guy and suddenly looked rather menacing. The guy backed off and disappeared into the crowd, mumbling something about not wanting trouble.
“I’m sorry about that. I don’t think he’ll bother you again.
Puck smiled and thanked him.
“Billy, this is my roommate, Puck,” I piped in.
“Puck?”
“Jennifer Pucket. My friends all call me Puck. And after that rescue, you’re my friend, too.”
So three of us got to talking. After a few minutes Puck caught my eye and nodded, ever so slightly tossing her head in Billy’s direction. I took the hint.
“Say Billy,” I said, running a finger down the front of his shirt, the first time we had touched, “would you like to go home with Puck and me?”
“Both of you?”
Puck and I both nodded.
He didn’t hesitate getting the check and paying for our drinks.
We got back to our apartment, and the door was barely closed when Billy pulled me to him and kissed me. It felt good to have a man’s strong arms enveloping me. I luxuriated in the feeling for a moment before breaking the kiss and pulling Puck into the embrace. The two of them kissed while I rested my head against Billy’s chest. Then Puck led the two of us into the bedroom.
She pulled off her top and unfastened her bra, letting Billy and I attack her breasts. We spent a few minutes worshipping those mounds, then she and I turned to Billy, pulling off his shirt and unfastening his fly.
We dropped to our knees and tugged his pants and boxers down and up sprang a most magnificent cock. It wasn’t long, only about six inches, but it was thick. My God, was it thick, the size of a Coke can. I just imagined what it would feel like inside me. I attempted to swallow it but could only get the head in my mouth. So I contented myself with licking the glans while Puck went after the shaft.
After a few minutes, Puck left his cock to me and moved around behind him, rimming him and licking his taint. He moaned in appreciation.
Soon, he must have been ready to cum, because he pushed both of us away, and then, with Puck’s help, stripped me of my clothes. Then he picked me up and lowered me down on the bed. The next instant he was between my legs, eating me out. He was good, not as good as Puck, or for that matter Mark, but more than adequate. Meanwhile, Puck removed the rest of her clothes and climbed onto the bed, lowering her pussy onto my face. I licked away.
After a bit, I felt that familiar warm feeling in my pelvis and my toes start to curl. I wrapped my legs around Billy’s head and shook with an orgasm. I kept trying to lick Puck’s pussy, but it was difficult to concentrate on the task.
When I finished rocking, Billy flipped me over and positioned me on all fours. I had almost forgotten what it was like to have a big man control my little body. I felt his cock enter me from behind, and it was as satisfying as I had imagined it. I found Puck’s pussy staring me in the face once again, and I commenced to eating her out for a second time while Billy thrust in and out of me.
Even with his vigorous thrusting, I was in a better position to give Puck the treatment she deserved, and soon she was rocking with her first orgasm of the night.
Then I felt Billy stiffen and his cock pulsate inside me as he pumped me full of cum. Then he softened and pulled out. I collapsed on my back, and Puck was on me in an instant, licking up the cum with her tongue. The moment her tongue touched my clit, a burst into another wave or convulsions.
The three of us fell together on the bed, me in the middle with Puck and Billy on either side of me. We just lay there in each other’s arms for a while, fingers gently running up and down each other’s bodies.
My hand drifted down to Billy’s cock, and I started to run my fingertips along it. It gradually came to life, stiffening once again. I turned him over to Puck, and she slipped underneath him as he gently fucked her while I watched. Watching was almost as much fun as being fucked. Almost.
When he came for a second time, I returned Puck’s favor and sucked the cum out of her pussy, and the two of use exchanged a cummy kiss. Billy just stared in amazement. I think if he hadn’t already cum twice, he would have instantly been hard again.
After we spent some more time in each other’s arms, giving each other the obligatory aftercare, we shooed Billy away. He went home happy.
Puck and I talked about inviting him back. I thought that I’d like to see him again, but Puck said that I needed a few one-night stands to give me perspective before jumping into another relationship. She was right. So the next day I texted him, saying that while it was wonderful, the two of us wanted to keep that night as a happy memory.
Sometimes I wonder what would have happened if I saw him again. Would the second time have been as magical? Or would it have been a disappointment? Would we have ended up dating? I don’t know. What I do know is that what happened next was even better.
A few days later Puck got an invitation from a friend of hers, Janine, who was organizing an orgy. Evidently this Janine had hosted orgies in the past, and this was the first since the lockdown had ended. Puck had never attended—it was strictly couples only, no singles, and Puck had never had a steady partner before. Janine said that she preferred male-female couples, but extra women were welcome, as some of the women were bi, but few of the men were. (That’s something I never quite understood. Two guys getting it on is hot, but I guess it’s a threat to their masculinity or something. Sometimes men can be so fragile.) Anyway, Puck wanted to go but could only do so if I agreed.
I was curious, but hesitant. An orgy was out of my comfort zone, but I was intrigued. So the next day I told Puck to go ahead and RSVP a yes for both of us.
I wondered what I should wear, but Puck said not to worry about that. We wouldn’t be wearing clothes for very long. So I settled on a little, black sheath dress and heels, panties but no bra; dress casual, but quick to shed.
Janine’s place was on Central Park West with a view of the park. It was large by any standard, and enormous by Manhattan standards. Janine and her husband clearly had money.
She greeted us at the door, kissing us both on the cheek, and ushering us in. She was tall and gorgeous, about forty and with massive boobs, which I later saw were enhanced, but a very artful job. Her blond hair had dark roots. And most striking of all were tattoo sleeves on both arms. Her husband, Hank, was a good-looking guy, about sixty. I surmised she was a second wife.
We were introduced around, but I quickly forgot most of the names. I was too nervous. I had a glass of wine to steady my nerves. There were six couples, all told. Most were older. All were good looking, but none as stunning as Puck and Janine.
I didn’t realize it at first, but as if some secret signal had been given, the couples started to pair off. Puck and I found ourselves talking to a nice forty-ish couple, Ed and Janey. They were regulars at Janine’s parties, and Puck told them we were noobs. I noticed Janey’s fingers running down Puck’s arm, and Puck took her hand and kissed her fingertips. I felt a nervous ball in the pit of my stomach. I turned to Ed, and he smiled. I thought I might as well go for it and smiled back.
He reached out and touched my cheek, brushing back my hair. I closed my eyes and felt his lips on mine. Then he took my hand and said, “Since it’s your first time, you might be more comfortable in a semi-private room.” He then led me into a bedroom. I kicked off my heels and let my dress and panties slip to the floor. He took me into his arms, holding me close and kissing me again. I could feel his cock pressing against my thigh.
After a few minutes of furious necking, I dropped to my knees and unfastened his pants, pulling them and his boxers down and seeing his cock pop up. It wasn’t anything special, but it was circumcised and decently sized. I took it into my mouth, deep throating it and playing with his balls and taint with my fingers.
He must have been close to cumming, so he stopped me and guided me onto the bed. He finished stripping and dove between my legs, lapping at my cunt. He was quite good. He started with kisses on my inner thighs and mons, before parting my labia with this tongue and then sucking on my clit. I came twice before he moved up and I felt his cockhead part my labia.
It wasn’t long before he erupted inside me. It was too soon for me to build to another orgasm, but I didn’t mind. We lay there chatting for a while. Ed was a really nice guy. And after a bit he suggested we see how the rest of the party was going.