Where it happened: neighbor lady's bedroom
Langauge: English
Sex: Male
Rating: 9
Category: Straight
Martha was my first lay, she was 39 and I was 18. We had just finished fucking ( I had just lost my virginity to her ). There I was standing before her wearing her full white lacy nylon panties. She looked confused and asked if I made a mistake and did I want to put my own underwear back on. I told her no and she patted the couch and had me sit down and tell her about it
She was sitting there nude fresh from our first fuck. Lovingly she put her arm around me and with tears in my eyes I told her how I would sneak and wear my Mom’s and Sister’s clothes. Mostly their bras, panties, slips, nylons, girdles and sometimes skirts, blouses or dresses if I had a lot of time to dress. Well I did not really expect this from you. She asked if I was queer and did I like boys. I said no but I would like to dress up for her and play like we were Mommy and Daughter. She said ok but that I would have to be treated like a little sissy. I eagerly nodded yes and put my head in her lap. She told me to come back next weekend and we would play.
I showed up next Sunday and Martha ushered me in and immediately told me to strip. She was wearing a black cocktail dress with black nylons and black high heel pumps. She turned slightly and had me follow her into the bedroom. Nearly on the bed was nice lingerie in white for me. She told me to dress while she watched. She sat at her vanity table and I quickly put on the bra, panties, garter belt, stockings, fullslip and high heels. She motioned me to vanity table, she rose, had me sit and placed a blond curly wig on my head. She had me stand up and told me to unzip her dress. It fell from her shoulders revealing her wearing a black lacy bra, bikini panties, garter belt and stockings.
She walked to the bed sat on the edge. She told me to come over and took the straps of my slip down and pulled the slip off. Next she hooked her fingers into waist band of my panties and off they came too. All I had left on was my bra, garter belt and high heels. My cock was stiff and Martha made lay over her lap and locked my dick in between her stockinged thighs. She patted my ass before giving me a few painful slaps with her hand. She parted my ass cheeks with one hand while the other searched out my anal opening and soon I was being fingered for the first time. I was moaning with being penetrated for the first time. She removed her finger, lifted me off her and had me lie on on the bed. She went to her vanity table opened the drawer and removed a srap-on dildo. Martha cinched it around her shapely hips.
Martha strolled sexily to the to bed and told me it was time for my defowering. She told me that if I wanted to dress like a girl that I needed to be fucked like one too. I began to whimper a little and she said don’t worry my little sissy. I’ll be as gentle as I can but it hurts the first time for all girls, especially for little sissies who are taking it up the ass for the first time. She lubed the dildo, slid a pillow under my ass to elevate my hips. Now sweety here it comes she said. Martha knelt between my legs lower herself down and pushed the rubber dick towards me, positioned it at the entrance to my shit shute. She moved her hips forward a little and the head of the her fuck pole poked at my virginal opening. She moved more and the head popped in and I screamed and cried tears of pain and joy. It did hurt, my ass was on fire but I was over joyed to be really getting fucked. I had secretly dreamed of this.
She began to move in and out of me and after a little bit the pain subsided and I was going out of my mind with ectasy. I bucked my hips to match her thrusts into me. Fuck me I yelled. Yes you little sissy she hissed. Her hand grapped my member and in a few seconds I was squirting cum all over us. When my throbbing subsided she pulled the dildo out of my ass. She kissed me hard on the lips. She handed me some tissue. I cleaned her and me up. She stepped out of strap-on, slipped her bikini panties off and told me to lick her to orgasm. I did and had get out of my girly clothes and go home with instructions to come back when ever. We spent the rest of that summer either me fucking her or her fucking me.
Processing your request, Please wait....
