Anal

Spin the Bottle

Mike and Tammy run into an old coworker and his girlfriend.

Spankmasters
Aug 8, 2024
15 min read
Spin the Bottlelgbtqpeggingcouples
Spin the Bottle
Spin the Bottle

Spin the Bottle

I sat in the mall food court waiting for Tammy. I was getting a little annoyed. She was running late, and I wanted to get out and enjoy this sunny Labor Day weekend. I really wanted to get home and hopefully get this cage off me. Seeing how that denim skirt fit snuggly around her ass and thighs, I couldn't wait to get home and rip it off.

Sipping on my soda I tried to calm down. I reminded myself how much things had changed in less than a year. Really how much everything had changed since that rainy night when Tammy picked me up. Now I was getting ready to move in with Tammy. Anna was staying over at least four nights a week. I was wearing silk red panties, a cage on my dick, and thigh high silk stockings under my jeans. In so many ways I had a new confidence and was happier than ever.

Finally, I saw Tammy swiveling her way towards me in the crowded mall. She was carrying a plain bag.

"So, can we get out of here?" I asked.

"Such an impatient boy, Mistress doesn't like that," Tammy said wagging her right pointer finger at me.

"I am only impatient because you look delicious," I said and pulled her closer.

"I know you hate coming to the mall, but I think you'll like what I got."

"What is it?"

"Weeelll, someone has a new red satin gown to wear for his Mistress and two people who like the Jets may get to see their Mistress in a cheerleader's uniform next Sunday," Tammy said with a mischievous smile.

"Oh, those do sound well worth the wait. I was wrong to doubt you Mistress," I said before giving her a kiss. For a second, I enjoyed feeling her in my arms.

"Mike!? Is that you?" a voice called out.

Turned around to see my former colleague Kyle standing there with a surprised look on his face.

"Tammy, what are you doing here?" Kyle asked. Tammy instantly blushed.

"Hey Kyle!! How are you?" I said as I stuck out my hand to him.

"I am good," Kyle responded, still seeming very surprised as he shook my hand. "How is the new job?"

"Going well so far."

"Good to hear. By the way, this is my girlfriend Samantha," he said introducing us to a strikingly beautiful, tall, black woman who had long, lovely, legs and a sleek figure that her yellow dress wrapped around. Kyle's blond hair, light blue eyes, gorgeous face, and chiseled body had been something I had started to fantasize about, now seeing he had a stunning girlfriend made me think that door was closed.

I stuck out my hand and shook her soft hands.

"It's a pleasure," she said.

Tammy stuck her hand out and they seemed to look each other over and smile as they shook hands.

"So, what are you two up to?" Tammy asked. I was surprised how she suddenly became interested.

"We just got out the movies," Samantha said.

"Great. What are you up to now?" I asked.

"Nothing, just going to go grab dinner nearby and then chill out at home," Kyle said.

"Cool. We're just wrapping up shopping," Tammy replied.

"Want to join us?" Samantha asked with a smile.

"Sure, I'm game," Tammy replied.

I could feel something was brewing between Tammy and Samatha. I understood that Tammy could sleep with Anna whenever she wanted but occasionally, she needed to go out with and even fuck other women. Our agreement was that Tammy had one free night a month, but I was the only man in her life. She was not allowed to bring anyone back to her place and if she didn't come home no questions were asked. I was wondering if Tammy would have her free night tonight.

The four of us went to a local bar nearby and were seated in a booth in the back and quickly got a round of drinks and ordered some food.

"So, Kyle, do you live around here?" I asked after we place our order.

"Yeah, Sam and I live about ten minutes up the road. How about you?"

"Well, I live on the other side of town, but soon I will be about 15 minutes from here in the other direction. I am moving in with Tammy."

"Great!" He replied.

"So how did you too meet?" Samantha asked.

We both blushed.

"Yeah, we worked together," Tammy said.

"They used to fight all the time," Kyle interrupted. "So, what happened?"

"Well, one dark and stormy night," I said in a deep voice.

"Very funny," Tammy interrupted.

"Well, it was."

"Ok, one dark and stormy night somebody was walking home with a busted umbrella," Tammy said pointing to me. "I saw him, gave him a lift back to my place and once he got out his wet clothes..."

"Oh, I like where this is going," Samantha said with a smile.

"We both started talking and the lights went out," I said.

"And he jumped in my arms afraid," Tammy interrupted.

"No, we both jumped each other's arms and found we had more in common than we knew and connected. From there it just started," I said as I turned and looked at Tammy's glowing face and felt her left hand on leg.

"Ooohhh, that's so great," Samantha said.

"But you kept fighting in the office," Kyle said.

"We figured it was best to keep it on the down low and keep up the front that we weren't together," Tammy said.

"You know how bad office gossip can be, especially on a new relationship," I added.

Samantha and Kyle nodded.

"How did you two meet?" I asked.

They both blushed a little.

"It was through friends annnddd shared activities," Kyle said.

"What activities?" I asked.

"We both hang out at the same clubs," Samantha said with a blush and instantly regretting it.

"What kind of clubs?" I followed up with.

"Social," Kyle quickly said. He sounded nervous. Kyle was normally so calm and cool, it was very surprising. Tammy tapped my thigh as though to say back off.

The waitress came back with our food, and we started eating.

"What movie did you two see?" Tammy asked.

"Secretary," Samantha answered. "It was playing at the art house theater on a revival run."

"Oh, a classic. I love that film," Tammy said with a smile.

"You do? Kyle and I love it as well. Have you seen it, Mike?"

"No. What's it about?"

"It's love story set in an office," Samantha says with a smile.

"Yes, it is, but it's not vanilla," Tammy says.

"Neither are we," Kyle says as he pulls Samantha closer. I had no idea what they are saying but Tammy is suddenly very happy. She put her left hand on my crotch.

"The same here," says Tammy.

"Mike, you seem pretty vanilla," Samantha says.

"I don't tan well," I reply.

Everyone else laughs out loud.

"Mike, you are the best," Kyle says.

"What the hell is going on," I whisper to Tammy.

"They are into the same kind of stuff we are into," she replies.

"I am Mike's Mistress and he's very new to all of this but he's a very good learner," Tammy said with authority.

"Oh, do you play with others?" Samantha asked as the flirting between them escalates.

"We do," Kyle says. "Would you two like to come over tonight."

"Yes, I'm up for it," Tammy said.

"Are you Mike?" Samantha asked.

"Yes," I said looking at Tammy as she winked at me.

Suddenly the food is an afterthought. We quickly finished it and got the check.

Before I knew it, we were following them down the street. I turned to Tammy.

"I thought you were only going to sleep with women. What about our rules?"

"Our rules are in place. I am not sleeping with Kyle. The only thing I want is that sexy girlfriend of his. She's got a cute ass, just like Anna, but not as nice as yours, "Tammy said while she reached around and squeezed my ass. "You are free to sleep with Kyle if you want. Do you want to?"

"I,I, I don't know."

"That's fine. Just go with it. Here's the key to your cage."

I took the key.

"Are you two coming?" Samantha asked as she looked back.

"Ok," Tammy said and grabbed my hand. We ran up to Kyle and Samantha. They were standing in front of an apartment building.

"This is our place. Come on in," Samantha said and grabbed Tammy by the hand and pulled her into the building. Kyle and I just followed. Samantha pressed the up bottom and bit her lip as she looked over Tammy. The door quickly opened, and we went inside. Kyle hit the top floor button and the door closed.

"So, how long have you lived here?" I asked.

"We moved in six months ago," Samantha said.

"Like I mentioned, I'll be moving in with Tammy at the end of the month," I replied.

"Great," Kyle said.

"You'll have to come over once I settle him in," Tammy said.

"Ooohhh, I like the sound of that. I enjoyed breaking in Kyle. He was new to all this. Don't you love it when the clean-cut boys turn out to be kinky?"

"It's the best," Tammy replied as she ran her fingers through my hair.

The door opened and we went down the hallway.

"Welcome to our place," Kyle said as he opened the door.

"So how did you find out that your all-American boy was into kink?" Tammy asked.

"We had been going out for four months and I was giving him an oil massage. We were both naked. I was rubbing his lower back and then his cute butt as I straddled him. I got really turned on and moved up to start working his upper back and I began to grind my pussy into his ass. He let out this moan. I asked if he was ok. He said it was amazing. I stopped massaging and started grinding. He told me he was getting hard. Over time I did more playing around with that ass, he liked it more and more, then one day I was pegging him. After that we moved to blind folds, spanking each other, threesomes, and foursomes," Samantha said as she looked us over.

"That great," I said.

"How'd you get started?" Kyle asked.

"I tied him up," Tammy said. Instantly everyone laughed and I nodded along.

"Yeah, she took away my clothes, tied me up, and dressed me in lingerie."

"Then I rode his dick until I came. He really fucked my brains out," Tammy responded.

"Damn, girl, you are an alpha. You don't hold back," Samantha said.

"This is her on a 4. Wait until she hits 9 or 10."

"Mike, would like something,,, to drink?" Kyle asked as he looked me over.

"Sure, wine would be great."

Kyle came back with two bottles.

"Want to help us finish this tequila before we get into the wine?"

"Sounds good," Tammy said.

Kyle poured four shots.

"What should we drink to?" I asked.

"How about clean-cut boys?" Samantha asked.

"To clean-cut boys," we all said.

We downed it and Samantha grabbed my hand.

"Let me show you both around while Kyle pours us some wine."

After a quick tour of their place, we were back in the kitchen. I don't remember much about it because I was staring at Samantha's legs and watching Tammy flirt with her.

When we entered the kitchen, we heard a pop. It was Kyle pulling the cork out of the wine bottle.

"Stubborn one," he said.

"Well with arms like that I am sure it was no problem," Samantha said as she put her hands around Kyle's right bicep. "Mike come and feel this."

I was stunned.

"Don't be shy Mike," Samantha said.

Kyle looked at me and smiled a little. He flexed. I felt his firm, round, 15 inch biceps. I felt a little flush and felt a little spit in the corner of my mouth. Samantha and Tammy watched on and smiled.

"Although, damn Tammy you have pretty nice arms to. Give me a flex," Samantha said.

Instantly Tammy did it and Samantha's hands were wrapped around her.

"Oooh, very nice. Mike isn't it great being with such buff lovers?"

I looked at Tammy and smiled.

"Yes, it is."

"Kyle isn't it great to have lovers with such cute, perfect little asses?" Tammy asked.

"Definitely," Kyle said as he looked me over. I now realized that Kyle wanted to fuck me. I was starting to get hard.

"I need to use the bathroom," I said.

Within seconds I was in there and taking my key out. I fidgeted with the lock and took off the cage. I splashed some cool water in my face and took a deep breath. I was ready to see what the night had in store for me.

I came out of the room everyone else was sitting on the floor in a semi-circle. My wine glass was there between Samantha and Tammy to complete the circle.

"Join us Mike," Kyle said with a smile.

"Let me just put this in our bag," I said.

I quickly returned to the room.

What's up?" I asked as I sat down.

"Tammy had this great idea," Samantha said. "Since we just finished a tequila bottle and its empty, why don't we play spin the bottle."

"Standard rules. The spinner spins twice and who they land on kisses. If people get matched up the third time it's seven minutes in heaven. I would say we go into the closet, but since we are all out of the closet so maybe the bedroom is better," Tammy said.

"Ok," I said.

"I'll spin first," Samantha said.

The bottle went around and landed on me.

"Oohh, someone gets to kiss my sexy sissy," Tammy said. I was instantly embarrassed and became beat red. "I'm sorry, that's private between us."

"It's fine, my name is slave and Samantha's is Queen," Kyle said as he gave me a reassuring look. I instantly felt better. Before I knew it the bottle was going around. Samantha gave it a real twirl and as it slowed down my heart pounded. Then it stopped.

"My slave is a lucky boy!! Give that sexy sissy a kiss," Samantha exclaimed as she clapped her hands.

"No tongues on the first kiss boys," Tammy said. "Which sucks for you Kyle. Mike is amazing with his tongue"

Kyle and I leaned towards each other. I was so nervous and turned on. He smiled, put his hand on my chin, tilted my head, and gave me a soft kiss. I felt a jolt of electricity, chills, and instantly pushed back and kissed him forcefully. I could feel my mouth opening.

"Break it up you!!" Tammy said. "Damn, if you guys get seven minutes in heaven that's going to be wild. Kyle it's your turn."

Kyle spun it and the bottle pointed to Samantha.

"Ooohh, someone's going to get very lucky," Samantha said with a big smile.

"Let's see who the winner is," Kyle said as he spun it. The bottle landed right between Tammy and me

"Two for one!!" Samantha said. "Come here girl."

She crawled toward Tammy, pushed the hair out of her face and gave Tammy a soft kiss. Tammy pulled her close and opened her mouth.

"Ok ladies don't leave Mike waiting," Kyle said.

Samantha pulled away, took a deep and exhaled, "Woah, that was nice. Come here Mike."

Tammy to turned and winked at me. I crawled over. Samantha and I put our foreheads together. We both smiled. She gave me a soft, slow kiss, I gripped her and kissed back. In going to grab her I lost my balance, but Tammy caught me. Samantha kissed me back with equal passion. When I pulled back we were both blushing.

"Uummm, Mistress you are a lucky lady."

"Yes, my sissy is a great kisser. Wait to you what he does with his tongue."

"Ok, Tammy, I mean Mistress your turn to spin," Kyle said.

"Thank you, slave," Tammy replied and spun the bottle. It landed on me.

Then she spun it again and it hit Kyle.

"Boys, bon jour, it's French time," Tammy said and Samantha laughed.

I leaned in, tilted my head, as I closed my eyes I saw Kyle smile. Within seconds I felt his lips. Kyle ran his hand threw my hair and I surrendered any resistance to him. I opened my mouth and let him stick his tongue in my mouth. My body got chills and I gripped his arms. My dick was so hard and throbbing. I moved my tongue with his but pulled back and enjoyed every second. Kyle pulled back. My mouth was open and my eyes were closed. Both Tammy and Samantha were hooting.

"Do you boys want seven minutes in heaven right now? That was hot," Tammy said, and I noticed she was holding Samantha's left hand.

Kyle was blushing and said, "let's keep playing, Mistress. Your turn Mike, I mean sissy."

"Thank you slave," I said and spun the bottle and it hit Tammy.

I spun again and it hit me.

"Bring it here sissy," Tammy said and gave me a slow, sweet kiss. Afterwards our foreheads met, and we both smiled.

"I love you Mistress."

"I know my sissy and I love you too," Tammy said.

"You two are so adorable," Kyle said. We both shot him an angry look.

"No, I'm serious," he continued. "It is really great to see you both happy together."

"Now it's the Queen's turn to keep this party going," Samantha said and spun the bottle. It landed on Kyle. We all looked at each other. I was praying for it to hit him. Then it did.

"Seven minutes in heaven!!" Samantha yelled and Tammy clapped her hands.

"So, what do we do?" I asked.

Kyle stood up and offered me his hand. I stood up and motioned to Tammy. She gave me a head nod and a smile that said everything was ok. I walked with Kyle to the room. He held my hand. He had a strong and reassuring grip, but his hand was also smooth. We got to the door and he opened it.

"Come on in," he said. My phone buzzed. It was a text message from Tammy. I motioned with my left hand for Kyle to give me a second. The message read, "Mike have fun. Love, Mistress."

I turned to Kyle and smiled. We walked in the bedroom, stopped, and closed the door. He took my hand and pulled me close. My heart was pounding. I could feel his firm biceps and looked down. He put his finger on my chin and lifted me up. We stared at each other for a second. Then he kissed me again. We both let our passions go. As our tongues met, Kyle pulled my shirt up and then stepped back. He unbuttoned his shirt and I saw his firm chest and six pack.

"Damn," I said as I walked toward him and then slid my pointer finger down his chest and traced his abs. Kyle grabbed my belt and undid it. Then he pulled my belt off and unzipped my fly. My heart was pounding. Kyle moved down as he removed my pants. He saw my panties and stockings. I was embarrassed for a second.

"You're so hot," Kyle said as he looked up. "I'll go put some music on."

I followed him over and grabbed him from behind. I felt his strong chest and chiseled stomach. I then began to kiss and lick his shoulders, before sucking on his left ear lobe. As the soft music began to play Kyle let out a smooth moan. I was so hard, and I started to grind into his tight butt. Quickly, I moved my left hand down and undid he belt, pants button, and fly. Kyle let out a sigh as his body got chills.

He turned, moved toward me, and kissed me. Our momentum carried us on to the bed. We rolled around, kissing and grabbing each other. Finally, when Kyle was on top, he took my right leg and pointed it straight up. He began to remove my stocking and follow it up with his tongue. I pounded and clinched the bed and let out a moan as my eyes rolled back in my head.

Kyle looked down and smiled. I grinned back at him.

"Shall I take off the other one?"

"First take off your pants."

"Can you help me?"

"Come here," I said as I mentioned to him with my right pointer finger.

He moved up like tiger over its prey. As he did, I moved my hand down and grabbed his pants. I slid them off him. The only thing he had on were black boxer briefs. I squeezed his ass and kissed his lower thighs. He pulled me up and then laid me back on the pillows. Kyle took off his boxers and flung them on the ground. His naked body was amazing. I was hard I was busting through my panties.

He quickly pulled off my left stocking and smiled at me.

"You have very sexy legs. I think Sam is jealous," he said. "Are you ready?"

"Yes," I said as moved up to his left ear. "Take me..."

Kyle slid my panties off and turned me over. He began to rub my ass and kiss my back. My eyes rolled back in my head.

"Have you ever been with a man?"

"No, but I've done pegging with Mistress."

"Ok. I am going to put on a condom and lube us both up. I am going to go slow tonight. We may have to do this a few times for it to be good."

'That sounds fine..." I said with a smile. "But you don't have to be sensitive me. I can take and I want it."

"You're amazing Mike."

"Thanks."

I got on my knees and stuck my ass up. Instantly I felt the cold sensation of the lube and Kyle rubbing it in my ass. My eyes rolled back in my head. Kyle then came up behind me and slowly began to thrust in and out. Although Mistress had used bigger strap ons, it felt different. Kyle picked up speed and I could feel him going deeper. His body was sweaty and it caused him to move quicker. The speed built up.

"Ooo!! Oohh!! Yes!!" I moaned.

"Yes, yes,yes!! You're such a hot little fucker!!" Kyle spat out as he pounded my ass. He started to groan. I could feel his dick pump as he came. Finally, Kyle let out a final exhale. He pulled me up and leaned my body against his. He reached his right hand down and began to stroke my hard dick. I opened my mouth and groaned hard. Within about a minute I felt a surge and was in pure ecstasy as I came on the bed. We both fell forward and were exhausted.

Kyle got out of bed and went to the bathroom. I watched his chiseled back and firm ass. He pulled off the condom and threw it in the garbage. He came back to bed and handed me a towel. I whipped up the cum on the bed. Then he pulled me close, and we kissed.

The door opened. Tammy and Samantha came into the room. They were both stripped down to their panties and bras. Tammy had her hand on Samantha's ass and I could see bite marks on the nape of Tammy's neck.

"You boys didn't forget about us girls?" Samatha asked.

They both jumped on the bed. It was just the beginning of an amazing night...

Tammy and I continued our outing, exploring the local bar as our new friends, Kyle and Samantha, joined us. Excitement filled the air as we discovered shared interests and experiences, particularly in the realm of Spin the Bottle.

"I've never played Spin the Bottle with such a diverse group," Tammy observed, grabbing my hand and giving it a reassuring squeeze. "But I think this might just be the most exciting game yet."

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