Mitch (Allyssa) and Paul (Nikki) 02

Story Info
The morning after Mitch and Paul get caught in lingerie.
1.3k words
4.66
5.4k
9
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Mitch (Allyssa) and Paul (Nikki) 2

I woke up the next morning in my girlfriend's bed. I was feeling a little hungover and kind of remembered just how much we all drank last night. The tequila really got me drunk! Then, I started remembering other things and wondered if everything that happened last night, actually happened or if I dream it. One thing I knew for sure was that I had to get up and empty my bladder!!

As I pulled the covers off me and started to stand up, I realized I was still wearing my girlfriend's red silky panties, bra, garter, and stockings! I am starting to think last night wasn't a dream. I think I remember actually enjoying what happened but surely that can't be right. After using the bathroom, I go to wash my hands and look in the mirror and see my red, smeared lipstick. Things are starting really click in my mind now. I keep telling myself that I am straight and I love my girlfriend and I am not interested in Paul and this was just a one time thing. I wash off the lipstick and strip the clothes off, noticing how good it feels having that material slide down my skin.

I go back to my girlfriend's bed and get under the covers, naked. My mind is just racing right now and then she rolls over and puts her arm around me and kisses me on the ear. Just for a moment, I thought everything was all good and last night was just a thing. I very quickly realized I was wrong when she whispered in my ear, "Good morning my Sissy Allyssa".

I was like a light switch went off and I suddenly realized everything that happened last night, actually happened and I am very conflicted because I now realize that I liked it. Her calling me her Sissy Allyssa was almost like a hypnotist saying the key word. She then asked me where my clothes were. I started to tell her that "I took them off" but in mid sentence she cut me off and said "You are my sissy now!!! You will wear what I tell you too and you will do exactly what I tell you to do or I will send the pictures from last night to everyone you know!, Understand???"

What could I say? I had to say yes but she reprimanded me and told me I was to call her Mistress from now on. I knew I might be in a little trouble and things would not be going the way I had planned before yesterday! Honestly, I was conflicted because I think I was OK with that idea while also feeling somewhat concerned.

She told me that if I didn't like what she had me wearing, she would have to pick out something else for me to wear. She went to her closet and her drawers and found a outfit she liked for me. She first had me put on a black garter belt and then dome black fishnet thigh highs and connect them together. She gave me a thong that was lacy in the front. I pulled it on and, the felling of the thong going between my ass cheeks was weird but exhilarating. Then came a lacy black bra. Honestly, I started to feel like I did the night before and was kind of liking this. She then took some rolled up socks and put them in my bra to make it look like I had boobs. Finally, she helped me put on a black and white maid's dress with all sorts of frills around it. There was no way any real maid would wear this dress!!!!.

Next thing she did was make sit down while she did my makeup and hair. She wasn't exactly happy about the results, especially my hair but she was content to let me stand up and said we were done with "trying to make you look like my sissy for now".

With that we walked out of her bedroom and walked into the kitchen and that's when I realized Paul had been through the exact same thing I had just experienced. He sat in a chair with the exact same frilly maid's outfit that I was wearing. It was almost like our girlfriends had planned this.

They made Paul and I cook them breakfast and then clean up the kitchen like "Every good sissy maid should do". After we were done, Paul and I looked at each other thinking we were done but the girls told us to get two of the kitchen table chairs and put them in the middle of the room. We did as we were told. That's when they told us to bend over the chairs.

So, here we are, two guys that got caught wearing their girlfriends' lingerie and were humiliated the night before and now we are dressed in some frilly maid's outfits laying across some kitchen chairs. Who would have ever thought either of us would be in this place???

Both of us were facing each other and our girlfriends did something familiar. They pushed our heads together to make us make out and then placed a belt around our heads to make us keep making out. Then they strapped our arms and legs to each of the legs of the kitchen chairs. Neither one of us could really move much. Honestly, with Paul's tongue in my mouth and making out with him, I'm not sure that I cared.

I guess some time had passed and we heard the girls say "Look what we have for you". All we could do was try to move our heads a little and see out of the corner of our eyes. There were our girlfriends standing there in what looked like latex or rubber black outfits but they were both wearing strap ons!

Things just got serious for Paul and I!!! Neither one of us had ever had anything in our asses. We weren't making out anymore and both had a much more concerned feeling. This was just going too far!!!

That's when I started to feel something cold on my asshole. I could see in Paul's eyes that he was feeling the same thing. Of course, that cold feeling was lube. I then felt a finger be inserted in a place where no one has ever been before. Then another finger and the a third finger. I felt like I was being probed and I wasn't sure I like it and by the look on Paul's face, I think he was feeling the same thing!

Then, there was a new sensation. Something much bigger than a finger was examining my asshole. My girlfriend then slowly pushed the head of her strap on into me. Luckily, there was enough lube and loosening up that it didn't really hurt but it was still a very odd feeling. Slowly she pushed her entire strap on into me. I could tell that Paul was feeling the same thing happen to him.

Both of our girlfriends, almost in unison, started to fuck Paul and I. They started thrusting into us harder and harder, faster and faster. Paul and I were still strapped together in the make out position so our faces just kept slamming into each other but we were both feeling something and we were making out now harder than ever. I felt like his tongue was going further in my mouth and throat than before.

I finally came without even touching my cock because I couldn't. Paul also came. I think that's what they might call a sissygasm. Our girlfriends undid our head strap and they each had a palm full of cum that they fed to us. I still have no idea if I ate my cum or Paul's. They left us strapped to the chairs as they went out shopping. Our faces were right up on each others and every once in a while we would kiss and make out simply because there was nothing else to do.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
KatiwantsKatiwants9 months ago

Mmmmmmmmm very intriguing 💓

Share this Story

Similar Stories

Making of Tina Ch. 01: Caught A story about forced feminization.in Transgender & Crossdressers
Your New Wife Femboy son turns his straight dad while mom is away.in Transgender & Crossdressers
Mitch and Paul's New Life Mitch and Paul get caught wearing panties.in Transgender & Crossdressers
My Roommate's Maid Pt. 01 College student forced to be their roommate's sissy maid.in Transgender & Crossdressers
Pleasing Mr. Wilson A summer job at the cottage leads to unexpected duties.in Transgender & Crossdressers
More Stories