Erika's Story

My name is Eric and I have been into crossdressing as long as I can remember. The feel of sexy silky woman's clothing has always been a real turn on for me. I honestly couldn't tell you when it started, but I can tell you it has progressed over the years. I have gone through my "pink Fog" phases where I would buy sexy clothing, only to be filled with shame about my dressing and throw it all away and promise to myself that I was done dressing up as a girl. Eventually times changed and I changed and decided that this is who I am and that I want it to be a part of my life.

I Had been Dating My girlfriend Mary for a while when I decided I was tired of hiding my crossdressing from her, But I had read plenty of stories online about men that got caught or came out to their wives / girlfriends only to have it screw up their entire relationship. I loved Mary at this point, and didn't want to hide this part of myself from her any longer. However, I didn't want to spring all of this on her all at once and freak her out or make her question my sexuality or anything so I decided to make a plan to slowly involve her over time and make it into something we could both enjoy.

Mary was about 5'3 and 108 lbs, and so beautiful I always felt special to have her. We had met in college in class, and apparently she had taken a notice of me from the first day. Within a few weeks we started to get lunch between classes and really started to click. Physically I wasn't anything special to look at as far as I was Concerned. I was about 5'8 and 160lbs,a bit nerdy but apparently had a sense of humor that worked wonders on her.

Several months had past and at this point we were having sex like bunnies and it was at this point that I devised my plan to involve her into my crossdressing. I knew I couldn't just invite her over and surprise her with me in makeup and lingerie and expect that to go well so I decided to keep it small at first and bring her into my dress up world.

Like most couples Mary and I liked having Netflix night and watching our favorite shows while snuggling on the sofa. Sometimes she would pick a movie I had no interest in but no matter, I'd watch the crappy movies anyway. One night over at her place watching some boring movie I noticed some bottles of nail polish on the coffee table. I grabbed a bottle of pink glittery nail polish.

"Why don't I paint your nails for you and make you all pretty, This movie isn't doing a lot for me anyway to be honest."

"That would be great," Mary responded. "I missed my appointment at the nail salon the other day and my nails look like trash."

I gave her a nice foot massage to relax her and proceeded to remove to old nail polish and carefully paint each toenail with the pink polish. It was the cutest shade of pink polish with little glittery sparkles in it. there is no way she could have known how badly I wished it were my nails that were painted.

"Toes are all done babe, would you like me to take a crack at the fingers as well?"

"Of course hun, a girl should have matching fingers and toes. You wouldn't want your girl looking half assed like she doesn't care how she looks would you?"

After removing the chipped old polish and giving her a nice hand massage with some lotion, I could tell she was really enjoying all this attention. Being careful not to screw up, I finished applying the nail polish and did a pretty good job if you ask me. Mary seemed really pleased with my work anyway and was noticeably appreciative.

After giving it enough time for her nails to fully dry I decided to take a small chance.

"Okay your turn to do my nails."

Mary cocked her head a bit like a puppy giving me a strange look.

"Why would you want your nails painted?"

"Well... I don't get to see you much during the week with class and work, and I thought it would be nice to see my painted nails and be able to think of you."

I could tell she liked the idea of me thinking about her when she wasn't around and quickly agreed that we should have matching nail polish so we could think of each other.

I was in heaven as she carefully painted all my nails to match her own. I had painted my own nails before when playing dress up by myself, but I had never had anyone else paint my nails for me. I felt good having this little secret between Mary and I. Once my nails were all dry and the erection in my pants went away, we snuggled on the couch and finished the lousy movie we were watching. At least she did, I mostly ran my painted fingers over her body and kissed her neck.

After the movie, Mary was apparently a little hot from the snuggles and kisses and decided we needed to continue the evening in the bedroom. We headed to the bedroom and I had half her clothes off by the time we hit the bed. I could tell she was really turned on and decided to press my luck and said

'I had no idea the painting my nails and running my pretty hands over you would get you so excited, maybe we should have had manicure night a lot sooner."

"I wasn't expecting to be so aroused by getting felt up by a set of girly hands, I've never been with a girl or anything before but I'm not gonna lie it was a turn on painting you and having you feel me up with pink girly fingers."

With that I pushed her back on the bed and spread her legs open and began gently kissing her opening. slowly I slid my hands up over her breast, cupping and gently squeezing her nipples. Feeling her legs tense up and clamp down on my head, I knew she was cumming from my tongue. I decided now was the right time to press my luck even further.

"If you liked my painted nails on your tits, then I have another idea to spice up the night."

With that, I picked up her pink microfiber panties and spun them around my finger with a devilish grin on my face. I could tell she wasn't sure where this was going but I figured there was no better time than the present and bent down and slid one leg into the opening, then the other and slowly pulled her panties up my legs. They were a tighter fit then I was used to, but the stretchy fabric felt incredible sliding into place.

Mary's eyes were as big as saucers, but it looked like she was going to play along and see where things went. Standing In front of a girl I loved, wearing nothing but her pink panties was a feeling a cant explain and I encourage all of you to try it out.

Before She had time to say anything, I hopped into bed and continued to kiss and fondle her. I could tell she was a bit surprised with where things had gone and her body was a little tensed up for a few moments but slowly I could feel her reservations melting away and she started to play along. If you have never been In bed with a girl wearing nothing but her panties while she runs her hands over your ass and moans about how turned on she is, then my friend, you have never lived.

I couldn't take it any longer and had to fuck her. I worked my raging hard on out of my pink panties and positioned it against her hole, Just then she grabbed my panty covered ass and pulled me inside of her. I was about as happy and turned on as I had ever been, I don't know If I ever thought I'd be wearing my girlfriends panties while we had sex but I was loving every second of it. To my surprise she was loving it as well, she wrapped her legs around me ass and was rubbing them against the soft material of the panties, this was more than I could take and I came like a firehose inside her.

Completely spent from some of the kinkiest sex of my life I lay beside Mary.

"Baby that was incredible, I don't know what made you decide to put on my panties and fuck me, but damn that was hot."

"I don't know either, maybe I was just feeling girly from having my nails done up in pink polish but to be honest, wearing panties gave me one hell of an erection, I might just have to do it again."

"Damn right you will do it again, with sex like that... my boyfriend wearing panties may become a regular thing!"

If she only knew how right she was...

To be continued...