16 at the time, sister 18, mother 41. 100% true story.
I grew up in a well to do, suburban neighbourhood in the Main Line area outside of Philadelphia. My Father was a union electrician and owned a rather large contracting business, thus affording us an upper middle class lifestyle. With that, my mother was able to stay at home and not work. Still, she was pretty busy most of the time raising me and my older sister Megan, all the while running and ruling the household.
Growing up in the stereotypical WASP household had its ups and downs. But, being a horny teenager with his mother always around usually meant more down than up. But, what happened to me in the summer of 1994 still tarnishes my otherwise normal, pleasant memories of my youth, and as to how I'm still viewed by my family.
With that said, I'll tell you I've always had a fetish for panties. As early as I can remember, from the underwear ads in the Sunday paper, an 'R' rated movie, to an occasional glimpse of my mother or my sister (only two years older than me). I simply loved panties.
July 1994, I was 16 years old, and on summer break. My sister had just graduated from high school, and was getting ready to leave for college in a few weeks. With dad at work, it was just a normal day around our household. My mother and Megan were talking about going shopping for some things for Meg to take to college. I was feeling really horny that day, and not just jerk off horny, I needed to 'play' a bit horny. They asked if I wanted to come shopping, but having them out of the house and having some privacy for a few hours seemed a better idea to me. The wheels in my deviant mind were turning. Panties!
After what seemed like an eternity, after lunch they finally left for the stores. My cock was already hard as I watched them pull out the driveway from the window. Once the tailights of my mothers Mercedes disappeared around the corner, I ran upstairs.
I've been secretly wearing my sister's and mother's panties here and there for a few years. It was risky behaviour in our church going household, and I tried to refrain from doing it as much as I wanted to (which was all the time!). But with the house to myself it was a special occasion. Panty wearing time!
I was a slight boy at the time. About 5'10', 130 pounds soaking wet. My sister on the other hand, was smaller. About 5'6', 110lbs. and I've recently noticed how tight her XS panties were becoming on me, and uncomfortable too for me to wear. But, I had a backup plan. Being around the same body size, I headed right to my mother's panty draw. What a sight to behold! All those soft, silky, lacy multicoloured delights folded in tight little anal retentive balls, waiting for me! I stripped naked right there at my mother's dresser. My cock sticking straight out, and my smooth hairless balls were drawn tight in anticipation. I chose a pair of satin low rise briefs. They were white, with a cute lace trim, and with little red polka dots throughout. I've seen my mother wear these before, sticking out her jeans when she bent down, causing a stir in my pants, wanting to see more, wishing they were mine. I hopped in the leg holes, and slowly pulled them on. What a feeling! So sexy, tingling,..... taboo!
I looked at myself in her dresser mirror for some time. rubbing myself through the delicate fabric. The briefs fit perfect, I was fully erect and wasn't sticking out, and I didn't have to push my hard cock to the side like when I wore my sister's panties. As always I wanted badly to cum in them right there. I've always wanted to cum in panties, but never did. Too worried about the evidence afterwards. But perverted desire overcame me this time. I was really going to do it. No changing my mind and pulling my cock out at the last minute, as I always did. I'll just do a load of wash real fast before anyone comes home. Wearing the panties, I went to my mother's bed, I grabbed her pillow and put it square in the middle of her bed, and began to hump. My legs were tight together as my panty covered cock thrust itself up and down on that pillow. It felt unbelievably good. My tight panty ass rose and fell in rhythm. What intense pleasure! With all this excitement, I never heard my mother and sister come back into the house. Caught up in the frenzy, I never did see my mother's purse sitting on her blanket chest at the foot of the bed. Had I seen it, let's say things would have turned out differently.
My eyes were closed, face drawn tight and I grunted softly as I humped that pillow. With the intense pleasure, I was close to cumming. Any second now. I was in paradise. Just then my mother entered the room to retrieve her purse. My eyes snapped open. 'TYLER!, WHAT THE HELL ARE YOU DOING?' she screamed at the top of her lungs. 'OH MY GOD! STOP IT! WHAT ARE YOU SICK?' My sister hearing the noise, came running up the steps into the room. She put her hand over her mouth and her eyes bulged out, in an expression that was half shock, half laughter. I froze, not knowing what to do. My mother ran to me on the bed. She grabbed a handful of my hair and held my head to her bed. the pillow still under my crotch. Tears began to fill me eyes, and the feeling of crying prevented me from saying a word. 'OH MY GOD, YOU LITTLE BASTARD! MEG, GET ME ONE OF YOUR FATHER'S BELTS' my mom yelled. My sister stood motionless, still with her hand over her mouth. 'MEG, GO IN THAT CLOSET AND GET ME A DAMN BELT!' my mother ordered. My sister snapped to, she opened my fathers closet, fumbled for a moment, and pulled out a large brown belt that my father often wore with jeans and handed it to our mother.
'Please no, I'm sorry' whimpered from my lips, as I was holding back tears. But, 'CRACK!' in one swift move my mother folded the belt in half over her head one handed, and brought it screaming down onto my ass! She held my head in place with a fistful of my hair. My sister stood watching wide eyed in awe. Mom hasn't 'given us the strap' since we were kids she thought somewhere in the back of her mind. 'CRACK, CRACK, CRACK' three more times the belt stung my ass. My panty covered ass was on fire! Oddly, as these hurried events soaked in, I realized my cock was still hard, and that before my mother caught me, I was just ready to climax. 'WHY? YOU DIRTY PERVERT! WHY? YOU PANTY WEARING FAGGOT' screamed mom. 'CRACK'...I began to feel a familiar feeling around my crotch 'CRACK' ...This can't be happening, 'NO!' I thought. 'CRACK'... hot cum blasted from my cock into the panties, quickly soaking through, creating a huge wet spot of cum. 'CRACK'...tears streamed from my eyes. As long as I was still laying stomach down over the pillow, my shame would remain hidden.
One more 'CRACK' and my mother pulled me up from the bed by my hair. Just then my sister pointed in horror at my crotch. 'Oh my gosh, ewww! look' All attention was on my groin. The wet spot in the front of the panties, had caused the fabric to become semi transparent. My dwindling five inch hard on was quite visible as it shot two more streams of cum onto the panties. My mom then slapped me across the face. I sobbed openly, saying 'I'm sorry'. By now Mom had calmed down enough to speak without yelling. 'Go downstairs and wait for your father' she said. 'Yes Ma'am' I replied, and went towards my clothes that were still piled in front of her dresser. She reached out and grabbed me by my hair once again. 'NO YOU DON'T!' she screeched. ' You want to be a panty wearing faggot. You'll sit downstairs in your faggot panties till he gets home' I pleaded 'But please mummy' Still angered, she snarled 'NO! NOW GET DOWNSTAIRS!' I walked out of her bedroom past my sister 'Dude, your fucked' she whispered. It was a little past 1:30pm now. I knew it would be about four to five hours before my father got home. I knew I wasn't in for a good night. My first time cumming in a pair of panties will be something I'll never forget.
To be Cont.....