Cross Dressing

It all started so many years ago, in the late 70's at the tender age of 19. My older brother had married this blonde German girl.

They were both 23 and she was about 5 foot 9 inches tall with a killer ass and 32 c cup breasts. I know because that's what it said on the tags in her bras. It was summer and we were all at the lake on his boat and she was wearing this scandalous (to me) yellow bikini. Her nipples poking hard into the material, her scent of wet girl and cocoa butter...all intoxicating. This went on for the early summer and I was constantly in a state of arousal. Then they moved away and my constant source of visual stimulus was gone.

One day while looking for something in a closet I came across her beach bag. Peering inside, there it was! That yellow bikini, still with the lingering scent of cocoa butter. Instant hard on material. I held it to my face and inhaled the scent of summer.

I had a lot of time, parents were gone all day, and I took that bag in my room where I had the strangest desire...I stripped all my clothes off and slid my legs into that bottom and pulled it up, filling the front with my tumescent prick. I then pulled the top on and tied it. Looking in the mirror in my bathroom, the sight didn't do much for me but oh my God, the feeling of the material against my dick and on my nipples...I blew a load right away without even touching myself!

That bikini became my primary source of pleasure that year. I would do my own laundry and I would wash those bottoms and get them out of the dryer and prance around in them with my constant erection so hard I thought it would destroy the bottoms.

Fast forward a few years to the mid 80's. I was 23, in the military and married. My wife wore lace hip hugger panties and after having our second child was basically frigid to me (but was fucking half the other guys in my company). I started to wear her panties under my uniforms. The feel of those fabulous lacey silken forbidden things under my macho man clothes was enough to keep my cock hard all day long.

Fast forward to 28 and I was divorced and living alone with the occasional lady friend. I would occasionally keep their panties when they spent the night and I would then wear them. Oh, heaven! The feel of the satin panties sliding up my hips to swaddle my cock and testicles in that slippery sweet feel. The roughness of lace against my glans as the panties held up my package under the boy clothes... Sweet bliss. I had also begun using enemas and getting good and cleaned out and using a vibrator in my ass during masturbation.

A new girlfriend introduced me to shaving my legs. She knew that i wore panties under my boy clothes as much as possible. One night she dared me to feel what it was like and after us drinking a couple bottles of wine, I took her dare.

We got into the tub where we cleaned each other up, including enemas and douche. We shaved my entire body from neck to toes (I still shiver with the memory) and rubbed lotion into my skin. She then put one of her red demi bras (with lace cups) on me while licking and nibbling my nipples. She then had me pull on a red satin thong, making sure to mouth my penis a couple times. She then pulled out the piece de resistance...a pair of black, lace top sheer stay up stockings. She rolled them up my bare legs, blowing warm breath on my legs as she did. She got each stocking up and the effect was intoxicating. She put an auburn long wig on me then applied makeup. I wasn't allowed to look in a mirror during the session.

When she was done she took off her pants and shirt to reveal a similar outfit underneath. She looked me in the eyes and said "surprise". She then said she had been wanting to try this for some time and figured it was time to go for it. She then put small 3 inch black heels on my feet, bade me to stand and we walked over to her full length mirror. I didn't make the best looking girl but oh did it feel good.

She stood behind me murmuring in my ear and licking my earlobe. Trailing kisses on my neck, she wrapped her arms around me and tweaked my nipples, making my cock jump in her panties. She told me to stand there and admire myself and she peeled away and went into the walk in closet. I was lost in the vision in front of me and running my hands over my panty clad cock and pinching my nipples through the bra, I had closed my eyes and heard her come up behind me. I felt her breath on my neck and her 34b breasts press against my back through her bra. Then I felt something I had not expected...something soft but hard pressing into the cleft between my ass cheeks. My eyes came open and she smiled at me and whispered shhhh, "I got you another present" in my ear. She was pinching my nipples and sliding her hand over my raging erection and rubbing her appendage in my ass cleft over the panties. We had played before with toys in my ass and I had slid myself into her back passage a number of times but the idea of be ingredients taken as I had taken her was exciting. She just kept rubbing and tweaking and dry humping away and I lost all track of anything but the feeling of euphoria I was experiencing.

She pulled me to the bed and turned me around, locking lips with me, our lipstick sliding together and mixing. Her hands cupped my ass as she lay me back on the bed, her lips not leaving mine in our shared kiss. Her hands left me and I felt her moving around before one hand returned to my cock and the other to my ass. Her tongue went to my nipples. I felt her pull the thong out of the cleft of my ass and her lubed finger slid into my silky passage. She again shushed me as she got in position and began teasing my man pussy with the tip of her cock. She slowly applied some pressure and slid her strap on into me. It felt huge, bigger than anything we had ever used and it seemed to take forever to get it in. We had done anal play but always with small objects in the past. My eyes just kind of rolled back in my head and I gave in to the sensation of that dick sliding into me.

She hit bottom and just held it there, letting me stretch and get used to the feeling of being full of cock. After a few minutes, she pulled out of me and told me to get on my knees. I did and she turned me to face the mirror. Then she pulled my thong to the side and slid in again to the hilt.

The vision was like nothing else I had ever seen. Here I was looking girly and my girlfriend behind me with her tips bouncing as she rode into me. She reached up and grabbed the wig to pull my head back and was holding my waist. On, fuck, the vision was a little overwhelming. She picked up the pace of her thrusts into me as my cock was pouring juice into my panties. My mouth was open and drooling and I could have dented steel with my nipples. My vision blurred and my orgasm ripped through me like a hurricane. My ass clenched and almost squirted her out, and I screamed my lust into the air.

She collapsed on me, driving her cock into me and pinning me to the bed as she ground out her howling orgasm with the dildo into my ass.

We lay there for some time while we recovered and she whispered "surprise, baby. I've been wanting to give you the fucking you've wanted for a while". I replied to just stay like that and she could do me anytime she wanted.

We stayed together for a couple of years and then drifted apart. During our time together, I would regularly shave and dress and she would fuck both my holes as often as I would fuck hers.

Eventually I would get the real thing, but that's another story.