When I was 16 years old, I babysat for my moms best friend. I had know Joanne (my moms bff) all my life, she was my second mother. and a single mother at that. And Joanne was smokin hot! Had thee biggest crush on her since i can remember. Joanne always wore pantyhose or stockings, and i mean always, one night i slept over at her house, i peeked in her bedroom and she was wearing a teddy and pantyhose, and ofcourse i had to masturbate, because like i said, she's a woman who gives an instant boner at first sight. Anyways, she had asked me to babysit her 2 boys on a friday night. Not a big deal even though id probably have been out with my buddys smokin and drinkin, but i said what the hell ill make a little money for once. So she left at 7pm and i was watching tv while the boys were upstairs playin video games. 9pm came around and i put the boys to bed. I got real bored watching tv so i decided to "snoop around". I went in the basement, in the laundry room, and what do you know, i found a basket full of dirty stockings and pantyhose. I instantly got a boner. i picked up a few pairs and put them to my nose. Oh how sweet she smells, my cock leaking precum at this point. I finaly got the courage to go into joannes bedroom. I walked over to her dresser and started rifling through her drawers. I found so many pairs of stockings, pantyhose, and sexy lingerie, i just had to wear some of it. So i put on a pair of white sheer to waist pantyhose, satin g-string, and a white satin bra. I layed on her bed, squirming and softly jerking my cock covered in pantyhose. i felt so dirty and sexy at the same time. So as i lay in her bed, i didnt hear her car pull in or her come into the house, all i heard was the knob of the door turn, and instantly froze. She walked in and saw me in her lingerie. "Ryan! WHAT THE HELL ARE YOU DOING!?!" I was so scared, my only reply was "Uhmmm...." She walked over to me, really scoping me out as she approached, sat down next to me, im trying to cover my still hard cock, she says, "you know, ive known you since you were in diapers, i had no idea you'd turn into this." I thought she was puting me down. "What would your mother think if she walked in on you like this?" I had no reply, and my boner started to disappear. She started running her hand across my silky thigh, and my boner came right back, she said" I won't tell if you won't tell!" I looked in her eyes, and she had that look on her face like she wanted me. I was stunned! She took off her coat, she was wearing a little black dress, black strapped thigh highs, 5 inch stilletohs, and pure seduction victorias secret body spray. She took off her dress, she wasnt wearing and panties or bra, and she was soooo sexy in those stockings, she pushed me back on the bed and got between my pantyhosed legs and started licking my silky cock! "oh my god!" is all i could say, Her tongue felt so good, she then stood my cock up in my pantyhose and she started sucking me right through them! my cock being rock hard now, she tore the crotch out for full access to my cock, it felt so good to feel the back of her throat with my dick. she shoved a finger into my ass wich hurt a little at first but instanttly felt good. she popped my cock out of her mouth, layed beside me, and said" your turn". I got off the bed and went to her feet, picked them up, held them to my nose, and smelled her sexy sweaty feet, shoved as much of her foot as i could into my mouth, licking and sucking her toes, her other foot wandered to my cock and she started rubbing it all over me, wich felt so fucking good. i licked from her ankle to her inner thigh, right to her dripping wet pussy and went to town, flickering my tongue all over her erect clit, pushing it inside her sweet tasting pussy. i shoved to fingers inside her and rubbed her gspot wile i sucked on her clit, she was moaning in so much pleasure, i couldnt help myself, i put her legs on my shoulders and eased my cock deep inside of her tight wet pussy. thrusting in and out of her made her moan even louder, she really enjoyed being fucked by a crossdresser! she rubbed her nylon covered legs all over the back of me, pulling me in deeper too! i pulled out and made her suck my cock again, she loved the taste of her own juices, then she got on her hands and knees and stuck her beautiful ass right up at me, i grabbed her hips and shoved my cock right back into her soaked pussy. pumping away like theres no tomorrow and she was just loving it, i pressed my thumb into her ass and she screamed with pleasure! so i wet her ass real nice and slowly eased my cock right in balls deep into her ass. SO FUCKING TIGHT i couldnt believe how good it felt. at this point im about to cum cause she just let out her climax orgasm! but she said to stop and i was like, ok... she pushed me down on the bed face down and said, dont move. I started to get nervouse, she went to her dresser, and got something, i didnt move like she said but it took her a minute to get whatever she wanted. she told me to roll over and i did. She was armed with a huge strapon! she said "your turn". She put my legs up on her shoulder and lubed her cock, and without preparing me, just slid it into my virgin ass. It hurt and i wanted to scream, but she covered my mouth, she just went right to town on me, fucking me like i was a girl. I felt so dirty and sexy again, my cock pulsing in pleasure. she fucked me for a good five minutes and then i felt pulses in my ass, she had one of those fake cum shootin dildoes, and she was filling my ass with cum, she screamed as if she were really cumming, and getting my ass filled felt so good i jerked my cock maybe 5 times and shot the biggest load of cum in my life all over myself. She pulled out and my ass ozzed with fake cum, and she got ontop of me licking up all my cum, collected it all in her mouth and french kissed me, it was actualy so hot cum kissing her. She told me to stay the night and sl**p with her. wich i had no problem with! So yeah, that was my first time getting caught in pantyhose.

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