Tammy Pegs Mike

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After weeks of buildup Tammy pegs Mike.
2.3k words
4.3
15.5k
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Part 5 of the 5 part series

Updated 10/19/2023
Created 08/27/2023
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JD8hrs
JD8hrs
36 Followers

I woke up Sunday morning with Anna standing over my side of the bed. She was already dressed while I was naked under the covers. Her green t-shirt was tight around her perky breasts and her jeans hugged her tight little butt.

"Good morning, Sissy," she asked. "You certainly are a warm-blooded guy. No wonder Mistress wanted you to spoon her. I only got to rub that firm butt while she had your hands all over her."

Anna made a pouty face with her lower lips sticking out.

"Are you ready for your big day Sissy?"

"What's going on?"

"Mistress says she'll tell you when the time is right."

"Can I ask you something?"

"Sure, Sissy."

"How long have you two known each other?"

Anna sat down on the bed.

"Well, we met three and half years ago. I was the first woman she ever dated or slept with."

"Really? How'd you meet?"

"One night I saw Tammy at a bar. She had on this short denim skirt, cowgirl hat, boots, and tight top. It was a country bar."

"I figured Anna."

"I went over and started talking to her. We hit it off. The flirting got intense. Her boyfriend at the time came over. I could tell he really wanted a threesome badly. I could see his boner even as we ordered drinks. I wanted her, so I was willing to get him over quickly to get to her. We went to his place. He watched us for a bit. We kissed and undressed each other. He then joined in. I got on top of him and fucked him while Tammy felt me up from behind. After those 3 minutes were over, and he came, Tammy and I went back to fucking. She was possessed. As you know when Tammy gets into it, she's amazing."

We both smiled at each other.

"So, what happened?" I asked.

"I saw her at the gym two weeks later. It was Pilates night and we started talking. She had dumped the guy. We went back to her place and fucked all night. After a few weeks of great sex and intense dating things cooled off. We realized what we had was mostly physical and rather than let a relationship kill that passion we agreed to just be fuck buddies. She has dated other guys and girls since then. She told me I could come over whenever she was with someone special."

"How often does that happen?"

"You're the first one she's called me in for. So, you must be special and after last night I would agree. Now, you are to come with me," Anna instructed.

Anna then took my hand and led me to the bathroom. I couldn't stop staring at her tight little ass but also felt good. I was feeling something for Tammy I had not felt in years. I didn't want to say it was love but I didn't know what else to call it.

When we got there, I stood in the doorway and saw that the bathtub was filled up a quarter of the way. Tammy came up behind me.

"Morning Sissy," Tammy whispered.

I jumped. She was right behind me in a bathrobe. Then I turned and hugged her tight.

"Well, good morning to you too. I love it when my Sissy is so affectionate. We're going to have a fun relaxing day and my beautiful Sissy is going to love it. Mistress promises."

"Get in the tub," Anna ordered.

I brushed Tammy's hair aside, stared into her eyes, and gave her a deep, passionate kiss. She clenched my body and kissed back with equal intensity.

"Do you want me in the tub? I'll get in. Anything for my Mistress but I want my Mistress in with me."

I stepped in and pulled Tammy toward me. Anna looked at Tammy and nodded her head. Tammy took off her robe and followed me into the tube. It was tight but I loved having her naked body next to me in the hot water. My heart was pounding.

Anna then turned the water on and poured bubble bath into the water. Then Anna began to move the liquid around as it filled up.

"Now we'll just sit here and get nice and comfy. Does Sissy want a mimosa?" Tammy asked.

"Sure Mistress."

"Anna go get Sissy a mimosa and croissant. And when you come back just be in your bra and panties. Mistress loves to have both of her guests wearing as little as possible," Tammy said.

I pulled her in close. She was now on top of me, and the water rushed in. Only my face was above the war.

"Sissy, do you like your bath?"

"Yes Mistress," I responded and moved my left hand down to the small of her back.

"Mistress, you know I am here because you have me. I don't want you to let go."

"I know. You're my Sissy. I am not letting you go either," Tammy said and then appeared to collect herself.

Right then Anna came in with the mimosa and croissant. I got even harder when I saw Anna was now in a red bra and red panties. She handed me the drink and food and gave me a wink.

"Anna, next time don't get dressed until your Mistress tells you. Next time you do that you won't get a spanking. You know I love your body. Sissy, do you like how Anna's dressed?"

"Yes Mistress," I said, feeling greater and greater pleasure in my obedience. With my left hand, I squeezed and began to massage the small of her back.

Tammy took her hand off my thigh and took the croissant from Anna. She began to feed me it. I felt like a child in her grip. A piece of the croissant got on my face and she licked it off.

"Yes, Mistress, I will never do that again. I promise," Anna said. "Should I give Sissy his surprise?"

"I think Sissy needs a minute. Let him have some of his mimosa," Tammy said as she got up a bit, so I could move over to sip from the glass. I then returned to my laid-back position. Tammy came back and we interlocked our legs. She was over me like she was going to do a push-up. I saw her firm right bicep and I squeezed it.

"Very nice Mistress," I said.

"Oh Sissy, likes his Mistress's arms?"

"Yes," I said then I leaned up and kissed her arm. My dick was ready to explode.

"Very good Sissy."

Anna turned around and bent over to open up the cabinet under the sink. She was wearing a red thong. Tammy felt my dick get even harder.

"You like that ass? You know I love it too. You can eat it later Sissy."

Anna turned around and had a blindfold.

"I heard you both. You can both eat my ass," Anna said and winked. "We share everything, don't we?"

"Yes," Tammy and I both said at the same time. We stopped and looked at each other. I kissed her again. I felt her melt into me.

"Sissy, it's time for us to stand up."

We unlocked our legs and Tammy got up. I followed her. Anna walked over and put the blindfold on me. Tammy got behind me and tied it tight. Then I felt Anna begin to towel me off. I heard the water start to drain from the tub.

I reached for the towel. Tammy stopped me.

"No. We are in control today. Just surrender and let us take you. Mistress promises you will love it."

Anna then began rubbing my head with the towel. The blindfold started to come off. Anna caught it and said, "Now be careful. Don't ruin the fun."

At this point, Tammy had stepped out of the tub.

"Step out Sissy," Tammy said.

I did and Anna proceeded to rub my legs and feet to dry them off. Then she wrapped the towel around my waist.

"Let's conceal that boner you've got Sissy," Anna said.

"Good job Anna," Tammy said.

Then there were a few seconds of silence. I imagined them kissing. The moment of their soft lips and tongues made me even hornier.

Tammy took my right hand and led me out of the room. We walked for a few minutes and stopped in front of the bed.

"Lift your left foot up and then down. Now do the same with your right foot. Lift your arms up. Hold still for a second, and now down," Tammy ordered.

I felt something smooth come across me.

"Do you like how it feels?"

"Yes. What is it?"

"Just enjoy Sissy. Mistress likes that you feel good," Tammy said as she grabbed me from behind and began to sway back and forth. Then she bit my ear lobe.

I exhaled and got lost myself in the moment. I could have stayed there forever. I heard a stomping noise. Then I felt someone in front of me. It must have been Anna because Tammy was still holding me. Anna ran her nails across my cheeks and then kissed me. I felt her lips then her tongue. Our tongues crossed and I felt a surge.

After we kissed our foreheads touched.

"Are you ready to, see Sissy?" Tammy whispered.

"Yes, Mistress."

The blindfold dropped and I was wearing a black, silk, nightgown. I looked down and smiled.

"Do you like Sissy?" Tammy asked.

I nodded and then kissed her.

"Turn around," Tammy said.

Anna had climbed on the bed and was on all fours. She started wiggling her ass.

"I want to watch you eat her delicious little butt," Tammy said.

I smiled and climbed on the bed. The smooth gown made me feel so sexy. Anna had taken her thong off. I steadied myself with my left hand and grabbed her right thigh with my right hand. I began to lick her inner thigh and then took a nibble of her right cheek. She let out an oouuhh. I moved closer and felt her legs underneath me. I grabbed her right cheek and then kissed it. Her ass was so firm. I then moved in and started licking her inner ass counterclockwise.

"Ooohh, God!! Yes! Don'tt dooonnn't stop," Anna started to moan. "Yeessss!!!"

I would lick, kiss, and then keep licking. She kept moaning. Then I moved down and licked her pussy. I then made a buzzing noise with my lips, and she tensed up.

"Yyyeessss!" Anna yelled.

I moved back up to her ass but she grabbed me with her left hand.

"Back please!!"

I moved my head down to her pussy and began to lick and kiss again. Anna began to moan again and she tensed up and released. This went on for a few minutes.

"Are you good Anna?" Tammy asked.

"Yyeessss Mistress," Anna replied.

Tammy then climbed on the bed and was over me. She pulled up my gown over my ass. I turned around and saw her squirt something into a tube. Tammy was wearing a strap-on dildo. I was nervous.

"Sissy turn around and let me oil you up," Tammy said. "Do you trust me? I am going

to give you the pleasure you have always dreamed about."

"Yes, Mistress, I trust you."

"Stick that sweet ass up in the air."

I did and felt Tammy's hand rub the cool lubricant in my ass. Anna rolled to the left side of the bed and held my hand. She leaned down and said, "Trust me, you'll love this. Mistress is amazing."

Then Tammy thrust in. The pain and exhilaration hit at the same time. I felt almost a white light. Then she pulled back and I surged with pleasure. She repeated over and over. Each time over going a little deeper. My eyes rolled back in my head. I was overcome.

"Ooohhh Mistresss!!!" I groaned.

Tammy moved faster and faster, deeper and deeper. The waves of pain and pleasure hit me. I clinched Anna.

"Oh Sissy. Yes!! You love it! Don't you?"

"Yes!!! Fuck me Mistress!! Fuck me!!"

Tammy kept going faster and deeper until it was a near frenzy. Then she let out a moan. I came all over my gown and the bed.

Then she began to slow down. Both of our hearts were pounding as she finally slowed down and pulled out. She took off the strap-on and threw it down. I looked up and Anna started to rub my head. Tammy then pulled the gown down and turned me over.

I looked up. She was sweating and red. We both smiled at each other.

She fell into my arms. I held her and Anna stroked both of our heads. Tammy and I interlocked our legs and felt her feet rub up against mine.

I put my right pointer finger under her chin and pushed her face up towards me. I pulled her towards me and we kissed. She rubbed her hands in the sticky mess on my legs and belly.

"Sissy, you're a dirty boy," Tammy said. "Anna please get a wet cloth for Sissy."

I looked deep into her eyes and couldn't contain myself.

"Mistress, I love you."

"I love you too Sissy."

We kissed and held each other.

After cleaning me up, the rest of the day we hung out. Anna left in the evening after our final threesome of the weekend. She kissed us both goodbye and told us she couldn't wait until next time. Tammy told Anna it'd be sooner than she expected and gave her a wink.

On Monday afternoon, I was getting ready to go home.

"Mike, before you go, I want to..."

"Tammy, I meant it when I said. I love you. We can decide how to move forward later but I just want to enjoy this moment."

"Mike, I feel the same way. I love you too. But you are my Sissy and I am your Mistress. You aren't leaving until you put on your chastity cage," Tammy said.

She undid my belt and pulled down my pants and underwear. Then she locked me up and pulled up my underwear and pants.

"Thank you, Mistress," I said with a smile. I turned around and left, knowing I would be back soon.

JD8hrs
JD8hrs
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AnonymousAnonymous6 days ago

Repetitive use of the term „Sissy”. Reads like a shopping list.

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