tagTranssexuals & CrossdressersBeen Caught Cheating

Been Caught Cheating


My story begins about a year ago. I had just moved in with my girl friend and we were completely in love. I was 22 and she was 23. Her name is Angela. She is 5'7'', 120 pounds, hour glass figure, C size breast, ghetto booty, light skin, long dark hair and green eyes that pierce your soul. She is and angel. I had moved out of my parents to live with her. We had been together for about 6 months when we decided we should get a place. My parents wanted me to get out and live on my own and experience life, and her roommates were stealing from her and not paying their bills. Everything was great. I was 5'11'', 150 pounds; white, with short spiky hair, a decent body. I drove an old firebird that everyone said was a "penis car." I started working at a law firm, just running around for lawyers and filling and shit work, but it paid great. Enough for me to live with Angela and have extra money to put in the bank so that I could buy a new car. As a hobby, I also swim. It keeps me in shape and I love the beach. I went to the gym to swim laps about every other day. I got so into it that I even shaved all my body hair off for speed, holding some dumb idea that I might one day be in the Olympics. Besides the job, everything was going great, until I fucked up.............

We had been living together for about 3 months. Enough time that she was comfortable with my friends and I was comfortable with hers. Our friends seem to drop in all the time and some didn't even knock anymore, just came in. we liked it like that. One of Angela's friends in particular came over all the time. Her best friend, Jenny. Jenny was 5'2'', blond, white and had huge tits and a great ass. She was a huge flirt and I would often catch her staring at me. She would also find the weirdest opportunities to touch me. Just little settle things like rub my arm, hold my hand too long when if I lit her cigarette for her. Things I didn't take in account that she likes me. Girls also seem to battle for guys, and I was the prize.

One day I was off from work because the lawyer I worked for was out on vacation, so I didn't have shit to do. As I'm lying on the couch in my boxers, Jenny comes in, pushes my legs off the couch, sits down and puts my legs on her lap. I was so into the movie that I didn't even really notice. I was watching The Professional, one of my favorites, and couldn't even care that Jenny was there. She was talking to me about her work, and how so and so did such and such to her and blah, blah, blah. About 3o minutes later, we were both watching the movie and she finally shut up. While lying there, she started rubbing my shaved legs. She commented on how smooth they are. This was exciting me and making me hard. Only wearing my boxers, she had to notice this. She kept rubbing and kept getting higher up my legs till she was rubbing form my thigh to my calves. I started biting my lip and moaning. I looked up and she was smiling. I should have stopped her. I should have said no. I coulda, shoulda, woulda. But I didn't. Then she leaned over and starting rubbing my crotch. This set me off into some hard moaning and heavy breathing. She took out my penis through the hole in my boxers and started stroking it. I also shaved my privates, so it felt so good to have her little soft hands rubbing my dick. I wasn't even watching the movie anymore. She got up and laid on top of me, and kissed me, while still stroking my dick. I should have stopped her. I should have said no. I should have said how much I loved Angela and told her to get out. But, I didn't. We kept making out, until she broke off the kiss and pushed her self down to my crotch and started going down on me. She sure could suck a good dick. I was moaning so hard that I grabbed the pillow from the couch and put it over my face to deaden the noise. Then, Angela walked in the door. She screamed, GET OUT!! Jenny shot up and just kept saying, "I'm sorry." Angela grabbed her by her hair from the back of her head, opened the door and shoved her out. She slammed the door and just stared at me. I thought she was going to kill me. I put the pillow over my crotch to hide my erection.

"What the fuck was going on?!"

"It's not what you think baby!"

"Not what I think, she was sucking your fucking dick!! How long has this been going on?!'

"Nothing has been going on, that just kinda happened. She was rubbing my leg, and one thing led to another, and I'm sorry hunny."

"You're sorry, YOU'RE FUCKING SORRY?! That's all you can say?!

She started crying. Then she was grabbing everything near her and throwing it at me.

"You piece of shit, I should dumb your fucking ass right now and make you go live back with mommy and daddy! I should throw you out while wearing your bowers and throw all your shit in the street. I should FUCKING KILL YOU!!"

"NO BABY DON'T, PLEASE, I BEG YOU. I'M SORRY, I'M SOOOO SORRY. PLEASE!! It was a mistake. I fucked up! I can make it right, I can fix this. I love you! I'll do ANYTHING!!"


"ANYTHING! I promise. I want to fix this. She means nothing to me. I love you. I want to be with you. Just tell me what to do, and I'll do it. Please let me make it up to you. I will do anything!", then I started crying.

I fell to my knees, and cried at her feet, just repeating, "I'm sorry", "I love you", "I'll do anything."

"If you really want to fix this, then you will have to give me some time. I love you too, and I want this to work as well. But my trust will be harder to get back. Now, when you say anything, you mean ANYTHING, right?"

"Yes, yes, I swear. I promise."

"Good! For starters, you can clean up around here. I'll be in the bedroom just leave me alone until I come out. I need some time to think."

With that, she went in our room, and slammed the door. I could hear her bust into tears, and saying "why" over and over. I felt so bad. Why did I do that, why didn't I kick Jenny out. Since all my clothes were in the room, I just grabbed some sweat pants and a t-shirt from the laundry room and started cleaning up. I went so far as to do the dishes and mop AND vacuum. Things that I never do. About 2 hours later, Angela still hadn't come out, and I was done cleaning. I knocked on the door to see if I should start dinner or go get some food. She said she would go pick up some food, as she wanted to get out of the house.

"I'll be back later. You can feed your self. I need some time to think, alone"

She left, and didn't even kiss me goodbye, like she always does. I could tell I really fucked up. I made myself a microwave meal. Feeling like I needed to get out as well, I went to the gym to swim some laps to clear my mind. I left a note saying where I was, grabbed my gym bag and left. I had to have been gone for about an hour and a half. When I got home, I could tell Angela still hadn't come home. About 10 minutes later, I got a call from her.

"I'm going to stay at my sister's house tonight. Don't worry; I'm not going to go fuck someone to get back at you. I just don't want to be at the "scene of the crime." I will be home tomorrow. Keep jenny away from there. I called her, and I don't think she will be going over there EVER again."

I tried to answer back before she hung up on me. That set me off. I started crying. I went to bed and even cried myself to sleep. I felt like such a little bitch. Since I didn't have to work for the next 2 weeks, I slept in. I woke up at about 3pm when I heard the front door slam. It was Angela. She came into the bedroom.

"Get up! We need to talk."

"Ok, I'm up. Are you ok?"

"No Tyler, I'm not ok. But! If you want to make things ok, if you really want fix things, I will give you another chance."

"Oh think you sweetie, thank you! You know will do anything for you!"

"Do you truly mean that, you will do ANYTHING?"

"Yes, yes, you know it. I promise, I swear on the moon!"

"Good. Then get out of this bed and go take a shower. And you need to shave; your legs look a little stubbly today. And use my shaving cream, it smells better than that nasty cheap shit you use."

I didn't blink an eye; I didn't even grab clothes to wear when I got out of the shower. I just jumped up and went to the bathroom. I turned the water on, waited till it was warm and jumped in. I sat under the water thinking. What was going on in her head? What did she have in store for me" what can I do to fix my mistake? I snapped out of and continued with my shower. I wondered why she would want me to use her flowery shaving shit. If I was going to smell like that anyways, why not use her shampoo and shower gel too. No point in smelling half manly, and half girly. I will just wash it off later with my Axe shit and get MY smell back. I will humor her this one day. I washed my hair with her Herbal Essence shampoo, shaved my body and face with her flowery shaving cream, and then washed up with her flowery body gel. Damn! I felt like a little bitch. Men do dumb shit when they're in love! I got out and dried my self and went on with my normal routine, comb my hair, and rubbed down with baby oil. I will also use baby oil before I swim to help with speed. I wrapped a towel around my waste and went into the bedroom. Angela was waiting for me, sitting on the bed.

"Finally, you are out. Come sit down, we need to talk. I though a lot about what happened yesterday. My sister helped me out a lot and gave me some advice. If you want to stay with me, you need to prove that our love is more important and that you need to earn my trust back."

She had something in her hand, balled up. I worried about what advise her sister gave her. I thought her sister was fucking crazy. She reached out and handed me the mystery object in her hand.

"I want you to wear these."

"Those are your panties!"

"No. These are YOUR panties. I bought them today."

"I don't want to wear those. I'm not a fag!"

"I know that, BUT, you did say you would do anything for me, and I want you to wear these. You wouldn't let a girl go down on you if you were wearing girly panties."

"That's true, I would want her that think I was queer."

"Good, then if you are wearing these, I know you won't cheat on me again and you can earn my trust back!"

I sat there in shock. I was the ladies man in high school. I can go to the club and pick up and any bitch there. But I defiantly wouldn't hit on a girl if I were wearing panties. What if I did get lucky? She would laugh at me. But, I do want to stay with Angela. I love her. I love our home together. If something that small would make her happy and make her trust me again, then I would do it. I mean, how long would it really last? A week or two?

"Okay. If it's what you want, then I'll do it."

"Yay! I'm glad, this proves that you are a real man and will do anything for his girl, right?"


With that, I took that panties and examined them a bit. They were bikini cut, pink and lacy. You couldn't get any girlier than that. I put one foot in, than the other and slid them up my smooth legs. I felt really weird. They felt really good, but they are for girls. I'm not a girl. I felt like such a little bitch. Standing there in front of my girl friend wearing panties that she had bought for me from Victoria's Secret. She smiled and just started at the panties and me. Then reached out and put her hands down the front and grabbed my dick and forced it between my legs.

"You need to tuck it a bit. If you're going to wear panties, wear them right. Not with a big bulge in the front!"

Now I really felt like a bitch. She had flattened my front and my crotch to look like a girl's. I couldn't wait for this to be over. With that, she pushed me on the bed and jumped on top of. Rubbing me through my panties. It felt amazing. I never knew something could feel so good. With her other hand, she pinched my nipple and started to pull and twist it, while sucking on the other one. I was in heaven! I wanted to fuck her so bad.

"Will you be good?"


"Will you cheat on me again?"

"No baby"

"Will you really do anything for me?"

"Oh yes!"

"Then eat me!"

With that, she jumped up, stripped off her pants and panties, and jumped on my face. I started licking her pussy up and down her lips. Burying my tongue into her, then pulling out and licking her clit. Sucking on it. And repeating. She was moaning and pulling my hair, hold my head in her crotch. She started rubbing her pussy harder on my mouth, fucking my face, riding my tongue. She moaned, and moaned, then screamed! Held my head deeper into her, and came. She cummed right into my mouth and I swallowed it all.

"Lick up the mess bitch!"

Her forcefulness turned me on, and I licked up the rest of her cum from her pussy lips till it was clean.

"What about me?" I said. "I want to get off too."

"What about you? You got off yesterday into Jenny's mouth!"

"No I didn't. I swear. And you have me so turned on right now."

"Oh, you want to cum too, do you little girl?"

"I'm not a little girl, and yes I want to get off too."

"Well you are wearing panties like a girl, so if you want to get off, you need to get off like a girl!"

Angela got up and went to our closet. She reached up to the top shelf and pulled down a little box. I wonder what she meant by getting off like a girl, and I found out real quick. She put the box down and went into the bathroom and came back with the bottle of baby oil. She opened the box to reveal a yellow, vibrating dildo. Then squirted some baby oil into her hand and staring rubbing the dildo up and down, lubing it up.

"What are you doing? I hope that's not for me!"

"Oh yes it is for you and that sweet virgin ass."

"I'm not a fag, okay! I don't want to use that!"

"You said you would do ANYTHING, remember? Now, will you do this for me, or should I just throw you out RIGHT NOW while wearing your pretty little panties?"

Dear god, I did not want to go outside, while only wearing panties. I didn't want ANYONE to see me wearing the panties. I didn't even want to wear them. So, I better just suck it up, I try to fix my relationship, anyway that I can.

"Please don't throw me out. I will do it baby. I will do it for you!"

"That's a good girl! Now, bend over the bed, and drop your panties down past your ass!"

I slowly got up and kneeled on the floor, turned around and bent over the bed. I pulled my panties down below my ass and waited for my punishment. She grabbed the bottle of baby oil and squirted some on my ass crack. I leaked down. Angela stuck her finger into my crack and rubbed the oil around. Then stuck her finger into my ass. I let out a moan, she began fucking me with her finger, then added another finger. I felt like such a bitch. She then pulled out and then grabbed the dildo. She stuck at right at my entrance and started probing. She pushed it in, harder, and harder, till I though it was going to rip me in half. I was almost crying. I was in tears it hurt so bad.

"It always hurts you first time. It does for every girl. I will feel good later. For now, you have to suck it up like a good girl and take this dick!"

With that. She turned on the vibrater and starting pumping me with it. I tried to take it. I tried to be a man about it. I gripped the sheets. Moaning, biting the bed. Trying not to scream. She just kept pumping it in and out of me. She reached down with her free hand and grabbed her panties from the floor that she was wearing earlier. She balled them up and shoved them into my mouth.

"There, that should shut you up!"

I couldn't believe it; she had never been like this before. What did her sister tell her? She just kept fucking me, harder and faster. It didn't take long. I was screaming into my panty gag when I came into the panties I was wearing. I clasped on the bed and just lay there, panting.

"You soiled your new panties I bought for you. Shame on you bitch! Take them off! Now, I want you to lick up your mess, then you will go wash tem in the sink and hang them to dry."

Without protest, I reached down, pulled the panties off, and licked my cum out of them. The salty taste was new to me and I hoped that it would be my last. I swallowed it up and continued into the bathroom where I washed them in the sink and hung them over the shower curtain rod to dry.

"After you clean your self up, I want you to grab a pair of panties from my drawer, put them on and get dressed, and then lets go eat. That is, if you are still hungry from your cum feast."

She walked off laughing at me. What has gotten into her? I did as requested. I went to her top drawer to find some panties. I didn't know what to wear. There were so many. I decided on a natural color and grabbed a pair of black lacy panties and them went to the closet to find something to wear. Then Angela walked back in the room.

"Oh my! That's so cute. If you are going to wear those, panties, you have to wear the matching bra. It will just look so good on your light skin."

"Why a bra? I don't even have breast. Why should I wear a bra?"

"Well, you are wearing panties that are a set. And if you are going to do something, do it right. Wear the set. It's just a bra, it won't hurt, and it's not like anyone will notice, we are just going to pick up some food and come back here. Just humor me. You did say you would do anything."

"Yeah I know. Okay, I will wear it, just because I love you."

"Good! It's in the next drawer. It's the same material as the panties, you can't miss it. And as for your no breast comment, we will have to fix that!"

I tried to comment on that, but she stormed out of the room before I could utter a word. I just shrugged it off and continued getting dressed. I opened her second drawer to find the bra. I wasn't hard to find, as Angela had said. It was an exact match of the panties I was not wearing, except, it was padded. I would have to find a big shirt or something to hide the bra. Everyone will be able to see it if it's padded. I just put it on because I could hear Angela telling me to hurry because she was hungry. I threw on some jeans, an old t-shirt and a hooded sweatshirt to try to hide my new underwear and slipped on my flip-flops and following my lady out the door.

It took me till I sat down in the car for the pain to register from my ass getting fucked earlier. Damn did it hurt! I couldn't find a comfortable spot to sit that it didn't hurt. Angela drove us to the next big street over where all the restaurants are. I thought we were getting some fast food. We just kept passing them all till the only places to eat were places where you go in and sit down. We finally pulled into Chili's, and it was a Friday night. It was packed.

"Are we really going to eat here?"

"Yes. Is that ok, or are you still full from all that cum you slut?"

'No I'm not full, I am hungry too, it's just I don't want people to see my underwear."

"Your underwear? You are wearing MY panties and My bra! YOUR panties are hanging up to dry because you came in them and had to wash them!"

She said that so load that other people in the parking lot looked over at us, some started laughing. I was so humiliated, that I just looked down and shut up. The dinner was nerve racking. The whole time I was scared we would see someone we knew, or someone would see the bra. The waitress kept giving me a weird look. I just wanted to leave. Angela reached over and popped my bra a few time and would die laughing. I was beat red. I wanted to run away and hide. When we got our food, I shoveled my down.

"That's no way for a lady eat!"

"Shhhh! Keep your voice down. Don't say that shit here!"

"Don't say what? Do you want me to go to each table and tell everyone what you are wearing, AND that you got fucked by my dildo today??"

"NO, NO, please don't!"

"Then shut up and eat your food like a good girl, and take smaller bites!"

Report Story

byrebeldoll© 9 comments/ 197414 views/ 47 favorites

Share the love

Report a Bug

2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: