Swinging Goes Awry: Beginnings

“I can see that.”

“You know, Winston likes you.”

“He does?”

“Yes, don’t you, Winston?” Mandy looked down at the hunk fucking her.

“Oh, yes, Mandy.” Winston confirmed. “I would love to take your husband as a lover. Would I be your first male lover, Bruce?”

“Unfortunately, no, Winston. You would be my second, and my second tonight.”

“What?!” My wife stopped fucking and sat up, shock written all over her face. “Explain.” She had a smile as she made her demand, so I knew she wasn’t jealous or upset with me, so I explained.

I told them how I visited the hesitant couple with their door open and the twin African boys and how one wanted me to suck him. Then how I left and ended up at Johnny and Mel’s room and everything that happened there. I explained how Samson asked me to suck him and I did and then how Ricky made love to me before really fucking me and how I came a number of times from it. At the end, Mandy was sitting in Winston’s lap, gently stroking his dick and playing with her pussy. “So I guess that is how I realized I was bisexual.” I finished.

“That is hot, baby. Don’t you think, Winston.”

“I can’t wait to fuck you, Bruce. I am surprised that Samson was eager for you to suck him off. He normally waits for his lovers to have much experience before he takes them.”

“I don’t know if ‘eager’ is the right word. I think he saw an opportunity and took it. Though I can see why he would wait for experienced lovers. He is packing a lot of heat.”

“How big?” Mandy asked me.

“He is both longer and thicker than me.” Winston responded for me. “Samson only takes the more experienced lovers into his bed. Your friends Mel and Johnny have been looking forward to this opportunity for many years. Mel has fought hard for her opportunity to take Samson and this year she managed to lure him to her bed. It is unlikely she will be needing other lovers during the rest of her stay.”

“Wow, bigger and thicker. I understand why he needs experienced lovers. I can barely handle Winston’s dick.”

“What a lie, baby. You been handling it very well.” Winston replied. I was a bit put off that Mandy let Winston call her ‘baby’ already, given that she and I used that term between us a lot. But I supposed there had been some intimacy in the room while I was out that I had missed out on. “So, Bruce, would you like me to fuck you in front of your wife?”

“Would you like to see that, Mandy?” I asked.

“God, yes. That would be so hot. But, can you suck him first? Like I did?” She asked.

“I suppose.” I replied, somewhat less confident in my dick-sucking abilities.

We repositioned so that Winston was sitting against the headboard of the bed with Mandy sitting beside him. And I was on my knees in front of him, approaching the cock that had rendered my wife nearly senseless with orgasms earlier. Winston was still fully hard, I supposed he hadn’t been kidding about wanting to bed me. Mandy was gently playing with her pussy and I could see that, from time to time, she would scoop out some cum from inside her into her mouth. I knew the intoxicating flavor of the men working here now and was envious that she had a reservoir of Winston’s seed to feed herself.

“I’m not very skilled at this.” I started, apprehensively, as I grasped the base on Winston’s cock and started licking it. He was still semi-hard and I could tell he was longer and thicker than Ricky.

“You’ll learn. You have lots of time.” Winston replied.

“Put it in your mouth, baby. I want to see it stretch out your lips.” Mandy requested.

I did as asked and, unlike with Samson’s huge pole, I was actually able to get Winston’s head into my mouth. I could taste my wife on his dick, as well as hints of his cum hidden in the pockets of the circumcised head. I got a couple inches below the head before I came back up and worked on sucking and licking it inside my mouth. Winston groaned in appreciation. “See, you are already getting the hang of it. Keep working it.” Winston’s hand went to my head and he started guiding me and giving me pointers on how to best please him. I was hard as a rock myself as I submitted to this sex god and learned from him.

Over the next several minutes, Winston got me to take half of his dick, with it grazing the back of my mouth and causing me to gag several times. By the end, his dick was very wet with slobber from the gagging and I was stroking him fast as I tried to make him cum.

“Okay, that is good, Bruce. You have been a good student, but it is now time for your wife to watch you get fucked.” Winston informed us.

“Goody!” Mandy giggled.

Winston had me lay down on my side at the edge of the bed with my knees up by my chest. “This will be the easiest position for you to take me in your ass.” Winston stood beside the bed and stroked his dick. He reached into the bedside table and pulled out some lube (I guessed it was standard in all the rooms), which he then applied liberally to his member. “Mandy, kiss your husband while I penetrate him. It will distract him from any pain.”

Mandy moved over beside me in the bed and I turned my head to accept her kiss. “I love you, baby.” I said.

“I love you so much, sweety.” She replied. “Thank you for suggesting this, I am having the time of my life.”

I felt Winston’s cockhead press against my sphincter and I reached for Mandy’s face and pulled her into another kiss as Winston’s dick pushed into me for the first time. He didn’t feel as thick as Ricky’s had been, which was interesting. I felt no pain as I kissed my wife, whether because of the distraction or regardless of it. Winston kept pushing into me until he reached some resistance, which was quite deep, based on my internal feelings.

“It is good that Ricky stretched you out. He is thicker than me, so you only need to stretch in one direction, as I am longer. How do you feel?” Winston asked.

“Good. No pain yet, I just feel really full. You can fuck me if you want.” I replied.

Mandy pulled away from me and moved so she had a good viewing angle and then went to work on her pussy with her fingers. “This is so fucking hot, sweety. I can’t wait for Winston to really fuck you.”

Winston took my cue to heart and pulled his cock out until just the head was in me and then thrust in. His dick glanced past my prostate on the way back in, making me shudder and groan in pleasure. Winston reached down and grabbed my cock between my legs and started stroking me externally as he also started a rhythm stroking me internally. As he fucked me, he pushed his dick deeper and deeper into me, breaking new boundaries until finally, he was fully inside me. He held himself there as he stroked my cock furiously, bringing me to my first orgasm. While my cock hadn’t had much use this evening, the amount of cum I dribbled out could only be described as piddling.

I grunted and groaned as my cock dribbled out its excretion while my wife watched with her hand buried in her pussy. “Did you come from Winston fucking you, sweety?” She asked.

“Uh huh.” I grunted out.

“That’s so hot. I can’t believe one man has made us both cum in one night with his beautiful cock. Did you know this was what we were in for when you booked this place?” She asked.

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