I met Pam in 9th grade band.She had come from a different feeder Junior High school.She was cute and was fun and didn’t take things too seriously.We fooled around a bit during our 4 years but never had anything other than heavy petting.We graduated and had significant others and went away to school or whatever but on our separate ways.
About 6 years after we graduated, we hooked up.Neither of us were with anyone anymore and we spent a couple of nights together.She had become more experienced as she put it and I guess I had too.We didn’t live nearby; in fact, we were about 2,600 miles away from each other.I really liked Pam but was never in love with her.When we hooked up, she was probably the least demanding of all of my partners.I felt very comfortable with her.
Fast forward another 7 or 8 years.Neither of us were in a good spot and I asked her out for dinner. We met at one of the better restaurants and ate, then sat in the lounge and chatted for a couple of hours.We bid each other adieu and went our separate ways once again.This time we were living in the same town.
About a year after our dinner, I called her up to see if she wanted to go out for the night.I had been dressing (almost ALWAYS inside only, but I HAD ventured to the big city for a ‘girls’ night’ kind of thing).We had talked a bunch and I got her sizes.Just because I’ve always had a desire for data, primarily.The day of our get together, I booked a hotel room so we could just be alone.I took some clothes and shoes and my wig and some jewelry to the room and put it all away.I went out to her house and picked her up and off we went. It was a little early for dinner so we went to the hotel first.We sat on the bed and made out, we talked a bit and I told her, “I have something I want to show you”.
I got up, opened the dresser and got out a sheer white blouse, some pantyhose in her size, a black knee length skirt with a floral lace over lay, like two skirts layered over each other and a pair of 3” black ankle strap heels.I told her that I had gotten them for her.I LOVED the skirt and it had been mine but I needed something to give her and it was perfect.I told her I’d wait in the bathroom while she changed.I asked her to not wear her panties under the pantyhose.She had done that all through high school and I never really cared for it.I got up and went into the bathroom while she changed.
While I was in the bathroom, I retrieved the clothing I had stashed there earlier that day.My ice pink satin bra and home-made forms, the same shade pantyhose as Pam’s, a very similar white blouse and my own black skirt.This skirt was similar in that it had a solid under skirt but with a very sheer overlay.While being knee length, I had cut the opaque skirt down to about mid-thigh, just for more visual impact.The jewelry I had was costume with clip on earrings, a big pink stone ring and a couple of cheap silver neck chains.I put the wig on and was ready to go when she said she was ready.I slipped on my own 3” black peep toe pumps and opened the door.
I told her I was a crossdresser and wearing panties and hose and skirts was an amazing feeling for me.She said I looked pretty good and that my ‘boobs’ looked better than a lot of women’s.I made sure they were big enough for my chest but not so big as to look clownish.She walked over to me and put her arms around my neck, kissed me and said, she “I kind of figured you crossdressed.The night we went to dinner I was pretty sure the black ‘socks’ you were wearing were to too sheer to be socks and not pantyhose”.
We ordered some food in, and chatted some more and ate and eventually I got her out of her skirt and we bumped uglies while wearing the pantyhose, before stripping each other down and getting it on for most of the rest of the night.
We got up in the morning, showered and I took her home.I told her that she was the only person who knew about my preferences for clothing and she said she knew and understood.
The following summer, I had accumulated more shoes and more dresses and more panties and better forms and more jewelry and on and on.I called her up to see if she had time to see Leesa, to which she agreed.We planned to meet at her house during her lunch hour.I shaved as close as I did the previous rendezvous and stepped into a pair of panties that matched the same pink bra.Hooked the bra around my shoulders and dropped in my forms.I carefully slid a new pair of thigh high stockings up my legs, and stepped in front of the mirror for my 40 minute make up session.Hours of youtube showed how to put on eye shadow for afternoons in the office, along with mascara, lipstick, a touch of color on my cheeks.On went new fake pierced hoop earrings and then my wig.I put on a more conservative pair of black pumps; what I called my lawyer pumps because they had a bit blockier heel and then got my new favorite dress.I got in the car, drove to her house and went up to her door.She was there before I knocked and I was welcomed in.Pam was doubly impressed with how I looked.I was complemented again on my fabulous boobs and I think she was about floored by my makeup saying I “looked better than most of the women she works with”.Adding “Your eye makeup is nearly flawless!”I thanked her and put my arms around her and we started making out.She unbuttoned the slit on the dress and started pulling it open so she could feel me up.Pam pulled back a little with a sly look on her face and said “this doesn’t seem to fit your persona too well” as she grasped onto my hardening ****, through the satin panties.She grabbed me by the hand and dragged me back to her bedroom.We got to her room and she pulled the dress aside at the slit and said “your panties are certainly bulging. It must be because you’re wearing those sexy stockings!”She spun me around, unzipped my dress and pulled it down over my “just right” hips and ass.I was told to take her slacks off her and to take her blouse off.There we were. Standing in front of each other in our lingerie.Pam was wearing a white teddy that barely contained her C cup breasts.I reached between her legs and unsnapped the crotch before laying her back on the bed and pulling the teddy up and away from her shaved pussy.We kissed and grabbed each other’s boobs and I ground my satin pantied **** against her glistening pussy.I stopped kissing her to take one of her full tits into my mouth. She ran her fingers through my hair.The hardening nipple under my tongue, and her grasp on my arm told me, it was time to move south.I slid down her body and planted my lips on her lips.I sucked them into my mouth while nibbling my way to her love button.
Swirling my tongue around her puffy clit, I slid a finger into her wet pussy and started stroking the roof of it.It wasn’t long before she started bucking and asking for my tool.I stood up, stripping the now soaked satin panties off, leaned forward on the bed again and dipped right into her.Having already had two children Pam had had her tubes tied so we had no fear of pregnancy.I pumped into her bringing her closer to orgasm when she stopped me and said “let me on top”.We flipped position and she started grinding harder than I could thrust until her eyes rolled back, she dropped her head to her chest and performed a nutcracker squeeze on my thighs that would make the Rocketts smile. When Pam caught her breath, she lay down on my chest and nuzzled in between my boobs.I rubbed her back and her ass and her thighs and kissed the top of her head.I still had a good hard on and I was flexing it in her tight hot snatch.She sat up and said, you need something too and slid down the bed while sliding my ****, sticky with her nectar past her lips into her mouth.She looked up at me with a coy smile as my tool was getting harder and fuller.I was getting close and she knew it.She stood up at the foot of the bed and asked me “are you a man or are you a woman?”I replied “a little of both, but I only like girls”.I sat up grabbed her hands, flopped back on the bed, rolled over with her and split her legs wide.I gave her flower a few licks to moisten her back up, ran my rod in balls deep and promptly came after a couple of dozen pumps.
She pushed me off and stepped to the dresser.She turned around and had a vibrating dong positioned at her pussy.She slipped in and out a couple of times before coming back to bed.Straddling me she asked if I was any good at giving blow jobs before teasing the dong around my lips and slipping it into my mouth.It had remnants of her juice mixed with my goo and it was a very interesting combination.She got off the bed and had me get ass up, head down on the bed.I did and she put the soft silicone rod against my brownstar and applied pressure while spinning it.My body spoke for me when my ass loosened and Pam ran her bedroom boyfriend deep into me.Our bodies’ lubes was enough for easy pumping and while she worked it in and out of my pulsing ass, Pam also reached between my legs and started stroking me.
I began to push back against her with the dong and my legs were getting a bit shaky.I dropped my self onto the bed as a second wave of sticky goo came forth.Pam managed to catch it in her hand and after withdrawing the ‘love muscle’ she wiped her hand in my gaping hole.I was still reeling from the double attack on me when Pam slipped out and back and put a tampon in my ass.She told me “itll keep you from soiling your panties, as the love potion leaks out.”
Pam went back in the bathroom for a short moment before coming back out and getting dressed.“I have to go back to work and you have to go, wherever it is you need to go” she said.I picked up my clothes, intending to get cleaned up but Pam told me “We don’t have time for you to clean up or shower.You need to just get dressed and head out”.Feeling a little bit like how many girls feel, used, I dressed and headed to the living room.I managed to get a look at myself in a mirror and wow, did I look like Id been rode hard and put away wet, which is exactly how I felt.My panties were very wet and sticky, my face had gotten pussy and dick juices on it smearing my makeup and there was nothing I could do to fix it.
