FIRST REAL SEX (best friend, mom, taboo)


FIRST REAL SEX (best friend, mom, taboo)
A few months after turning 18, now a freshman in college, I attended my first frat party. It was late October, on a Saturday night, when I and my high school friends, male and female, all attended, even though some of us were not in the same college. Needless to say, I and my group got smashed at the bear bash. We stumbled out of the frat house around 11:00. I had to drive a few friends home. (We all lived within blocks of each other.) I made sure, Kara was the last.

Kara lived a couple of blocks from me. So, as we approached her apartment building, I asked if she’d like to stop by my house first. My father was at an all night card game, and my mother was out at a club with her girlfriends and wouldn’t be home till after 1 am. It was 11:30 at the time.

Kara and I went to grammar school and high school together. She was about 5’7″, with a thicker build, but not fat by far. Her hair was short and brown. With smaller hips and a B+/C cup, I was sexually attracted to her for the previous 2 years, but chose to take a petite little girl to the prom and passed up Kara. Since both girls were in my group of friends, I was afraid to ask Kara out. I had known for a while that Kara had a crush on me. I was also sure, or pretty sure, that she wanted to play with me as much as I wanted to play with her.

She said yes. We parked and headed up to my apartment. We walked through the dining room, my bedroom then my parents’ bedroom to the living room, took our jackets off and sat on the sofa. I moved close, and we kissed. Lip to lip, then tongue touch and right into heavy petting. We kissed heavily for at least 30 minutes. During our passionate kisses, I managed to open her blouse and pants as well as mine. My hands found her beautiful breasts over her bra as we dry humped, my hard cock separated from her soft pussy only by her thin panties and my jockeys. I pumped my hard on along the crack of her pussy as I toyed with those great tits.

My fantasies about Kara for the past two years got the best of me. I felt my cock get harder and my young floppy balls pull up. The pressure in my cock built to a blast. Spasm after spasm, I shot my load into my underwear. I slowly came down from that great cum and realized time had passed and my mom might show up. We dressed and kissed. Then Kara left.

I never got to her tits or pussy, and, obviously, didn’t get to fuck her. Maybe that was good. I would have shot a lot of cum in her pussy had we actually fucked. Anyway, I showered, put on shorts and a tee shirt and went into the living room to watch TV. I was still drunk, and I was still very horny. As I sat on the couch, I realized that if we did go any further, I didn’t quite know exactly what to do. Other than simple French kissing that I had done with my prom girlfriend, I had never gotten a girl to let me go that far before. As I pondered what I would do next time, my mom came home. It was obvious to me that she had had one too many cocktails.

I knew her routine, after a Saturday night out with the girls, and that night was to be no different. Our family always hung out in their underwear. Mom would wear a house dress if she was home for a few hours or more. However, I often saw her in girdle and bra, sometimes with a garter belt and stockings. I knew she would go to the bathroom, take her clothes off and go to my parents’ bedroom. In our apartment, you had to go through one room to get to another. Their bedroom was next to the living room, with an arch between. Mom’s closet was off the living room. So she had to go through the living room to get to her closet.

I stared at the reflection of her D cup breasts in her dresser mirror, through the arch to her bedroom. Her bra cup was wide and I could see her great cleavage spilling out on top. She was 51, 5’2″ with small hips and a little bit of a belly. Her girdle and long line bra held that well in. Her skin was milk white, and her hair naturally red. Her shorter hairdo was redone each week at the hairdresser’s. She had slim shapely legs and always wore some sort of a heel, even in slippers.

Still wearing the garter belt and stockings, along with the long line bra and panty girdle, she sat on her bed and put some things away. I sat on the couch, and watched through the arch. She didn’t notice. I desperately wanted to see, touch, kiss and lick her beautiful tits. I loved her tits since I used to play with them as a toddler. I wondered what her pussy would look like with that red hair. Was it a thick bush or sparse. I wondered where she liked to be touched. Mom finished up in her bedroom, got up and headed toward the living room arch on her way to her closet. She was on her way passing me. I don’t know how the words came out of my mouth. It must have been because I was drunk and I knew she was too. I heard myself say, “Kara came over after the frat party.” She responded, “Oh that’s nice.”
“Well, we played around a bit, and I need your help,” I said. She looked surprised, nervous and a bit upset. “We didn’t do IT, but I wanted to. I realized that I really don’t know what a woman likes, where a woman likes to be touched, how a woman likes to be touched, and more.” I continued.

“What help do you need?” mom asked.

By now she was sitting on the sofa with me. I moved a bit closer, put my hand on her arm and said, “I need you to show me.”

With that, I slowly moved my hand up her arm until I reach her shoulder. I moved my finger over her bra strap and began to move it toward her arm. I then moved my other hand over her shoulder and slowly pulled the other bra stra toward her other arm. She didn’t move. Amazed at my boldness, and shocked by her lack of movement, I wondered how I was getting away with this. It had to be that she was drunk, a bit horny and my father would not be home all night. The straps moved along, down her upper arms until each strap rested down near her elbows. Her very full bra dropped a bit. I could then saw how her breasts looked when free. They didn’t sag. They were full and round and white.

As her bra fell a bit, I was able to see the edge of her big pink aureola. I wanted to see her tits free of that bra. “Show me what you like,” I said as I reached for her breast. I started at the top and brushed my finger along her breast, left to right and back, into her cleavage and out, brushing along the exposed edge of her aureola. My cock was a rock. My hands ever so slightly shaking, I teased her full breasts, almost tickling them with the tips of my fingers. As I moved down, when I got to the edge of her aureola again, I started to edge her bra down, a quarter inch at time. Her big pink aureola more came into view with her nipple still covered by her bra. Thank goodness I had cum a short while ago, or I would have blown a load already. I got my courage together and pulled the bra down a little further and her hard pink nipple presented itself. I let out a low moan as my fingers moved along her breast, teasing and tickling, until I arrived at her nipple. “What do you like?” I whispered.

“Touch it,” she whispered and let my fingers tease and tickle the tip of her hard pink nipple. I heard a low moan. Her eyes closed. Her breathing picked up a bit.

I teased both her nipples in this way, and she let herself relax back into the sofa. Her eyes were closed and her legs were slightly spread. Her head rested on the back of the sofa. I had her bra down, so all of her beautiful tits were exposed. My fingers tickled all over, paying special attention to her nipples. Her moans got a bit louder. I leaned over and let the tip of my tongue touch the tip of her tit. I was seeing stars as I tickled her nipple with my tongue. I let my tongue tease all over her aureola again paying special attention to the tip of her nipple. The more her moans grew more bold I got.

As I continued to tickle her tit with my tongue, I let one hand slide slowly down her belly, over her panty girdle to the garter belt and then on to her thigh. I was hoping her girdle was crotch-less and hoping she had removed her panties in the bathroom. My fingers ran ever so lightly along her upper thighs when I whispered, “What else do you like?” and moved my fingers up to the end of her leg, lightly brushing next to the outside of her pussy. She had sparse hair, so I was able to tickle the skin right next to her pussy.

“Move your fingers up,” she whispered back, and I did as told. She directed my fingers until i was touching her clit. My fingers barely touching her hardening clit. She let me know she liked it with louder moans. The tips of my fingers tickled and teased her clit. I watched her writhe as I masturbated her pussy. I continued for minutes. “Don’t stop,” she said in a slightly huskier voice than normal. I did as told. Her writhing grew stronger. She began to stiffen. A louder low moan came from her throat, and she came. She shuddered for a while, and I slowed, but didn’t stop, my clit teasing.
“Put your finger in,” she uttered. Again I followed her direction. My middle finger penetrated her warm pussy. It was ready for me. My finger slipped in easily. I slowly finger fucked her. My head was spinning. Was she drunk enough to let me go further? I couldn’t believe my nerve in getting this far. I continued a slow finger fuck her tight pussy. Her moans were near constant.

I heard, “Put it near the edge.” I didn’t dare ask her what she meant. I didn’t want to ruin anything that was going on. So, I figured since she let me go this far, she hopefully meant put my cock near the edge of her pussy, because that’s what I was about to do.

I stood up, pulled down my shorts and lifted her crotch-less girdle a bit. I was rewarded with her having already removed her panties. There was her pussy, lightly covered in red hair, begging for my cock. I reeled. I was seeing stars as I moved into position with her leaning back and legs spread. I moved down so my hard on would touch her pussy lip. Fireworks were going off in my head. My cock-head teased her lips and clit.
“Put it in.”

It was really about to happen. My rock hard cock was sliding up and down my mother’s pussy and teasing her hard clit with the top of my cock-head. I could feel every inch of her waiting hole tingling my hard-on. Explosions were going off in my head.

The head of my cock slipped into her welcoming pussy. It felt sooooo good. I pushed further and my hard shaft felt the inside a a pussy, in fact the inside of my mother’s pussy, for the first time. I couldn’t believe the sensations I felt on my head and along my shaft . My hard on slipped all the way in and my young floppy balls touched her smooth ass. More fireworks blasted in my head.

I noticed her eyes were back in her head as she moaned out loud. I pulled my cock slowly out. I wanted to feel my cock-head touching her lips and sliding all the way in again. My cock was bursting with feelings as I slid my cock-head and shaft all the way in again. This time a bit faster. My balls made a slight smacking noise as I entered her to the hilt.
I began a slow fucking motion. She told me how she liked it. I fucked her in long strokes, picking up speed as my climax grew closer.

“Fuck me,” she muttered in a whisper, and my speed picked up. I thrust my hard on, slamming my balls against her ass with a loud smack each time. Both our second orgasms were coming quickly.
Again, she muttered, “Fuck me!” I pounded her pussy, thrusting my cock, boiling up. I still couldn’t believe where this night wound up. Here I am, pumping my mom’s pussy with my rock hard 18 year old cock. My mind saw and felt one thing…my cock, here tight pussy and cumming. Just then, she stiffened a second, then started to shake.

Her moan started and didn’t stop. I couldn’t take it. I felt my cum pressure building, building. I shot and shot and shot, filling her pussy. Blast after blast, my cumming seemed to go on and an, as did her moaning. It seemed minutes before I stopped cumming and her moans silenced.

more to come…

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