My name is Jacob. I am 21 and I work as a materials handling specialist for a Chicago construction company. It pays very well, and while not always the most exciting job in the world it does have it's moments, like the time we ordered 500 toilet seals and received 500 toilet seats. But I digress. This story is about my Senior Prom. I had just turned 18 at the time and was dating this beautiful young woman named Stella. Blonde, blue eyed, 46 DD with a nice big ass. She was the object of my teen angst. I had chased her since we went to middle school together. While she was without a doubt the most beautiful girl I'd ever seen she was also a devout Catholic and Virgin. The most we'd ever done was kiss and pet but I have to tell you, she put a lot of herself into those kisses. I never failed to achieve an erection just from her kisses. She would wrap her hand around my stiffening cock and pump it while I bucked and jerked around. Always, just as I was ready to cum she'd bend down and kiss the tip before releasing my penis from her grip. She would proceed to tell me how someday we'd be able to finish when we were finally married. Then she'd leave me in a state I can only describe as a bomb waiting to go off.
I used to masturbate so much my Mom would always end up walking in on me. There I'd be, on my back, cock in hand, jerking myself to release. The first time she caught me, I was horrified. I had just started to orgasm when my bedroom door opened and there stood Mom, a basket of freshly laundered clothes under her arm. I gasped as she dropped the basket. Even though my hand flew off my cock it started to spew. I lay there helplessly as my semen splattered my abdomen. Mom just looked from my face to my stiff cock. A hand flew up to clutch at the neck of her dress and then she turned away. She left without as much as a word. I quickly found a towel and wiped the sticky mess from my abdomen. I dressed and picked up the laundry basket. Holding it in front of me like a shield I walked down the hallway to the dining area where she stood, back to the room, staring out the window. She didn't turn around when I walked into the room.
"Mom..." I called, trying not to look in her direction. "I brought your laundry out." When she didn't say anything I continued. "I'm sorry I was doing that. Please don't be mad at me." This did get thru to her.
"I'm not mad at you, Jacob," Mom said, turning around to look at me. "It isn't like you did anything wrong. Masturbation is normal and everyone does it." When I didn't look up from my feet she added "Everyone does. It's okay. Even I do occasionally."
I quickly looked up to meet her eyes. She smiled and nodded her head slightly. "It's true. Even women my age still need to find relief. If no guy is around to take care of her needs a woman has to do it herself. I just wasn't prepared for the sight of your...your penis. I mean....(she blushed and clutched at the neck of her dress again)...ejaculating like that."
"I am so embarrassed right now." I stammered. "I'll never be able to face you again."
"Really, Jacob, it's ok. It's normal to jerk off from time to time, although I assumed you and Stella were sexually active. I just assumed she was taking care of your needs."
I rolled my eyes and looked back at the floor again. Her words had struck a nerve. I was feeling low before, when she'd walked in on my wanking session. Now I felt like a total looser. I had reached the ultimate low point in my young life. Mom must have sensed something for she walked slowly over to me and gently took my chin in her hands and brought my head up until our eyes met. She leaned forward until her face was inches from mine. I could smell her perfume. Even in my low state I was aware of her as a woman, a desirable woman. I could feel the warm weight of her breast against my arm.
"Are you a virgin?" she asked, her eyes never leaving mine own. I tried to look away but she held me. "Look at me, Jacob..." She leaned closer and now our lips were but a hair's breadth apart. I could feel her nipple poking into my arm. My poor cock started to stir. I guess he had no qualms about kissing Mom, even if I did. I started to sweat as I knew she'd soon feel the pressure of my rapidly stiffening cock. I couldn't seem to think, either. I couldn't breath. My eyes locked with hers and I slowly nodded. She smiled sweetly.
"It's nothing to be ashamed of, baby." She brushed her full lips across mine. I was lost in the overwhelming sensations. I felt my manhood press into the soft flesh of her tummy. "I think it's admira...." Her voice trailed off as she realized what had happened. She stepped back a little and looked down at the tent in my pants. Her eyes were really big and I saw the tip of her tongue flick out to wet her lips. Her small, delicate hand reached out and gently squeezed the tip between her finger tips. I let out an involuntary moan.
I am not sure what made me do it but I asked her how often she masturbated. Without looking up from my massive erection she mumbled something incoherent. Her fingers deftly undid the buttons and zipper on my pants. As she slid them down my hips she slowly dropped to her knees. I stepped out of them at her insistence. My shorts were next and I was a bit embarrassed as when she lowered them and my rock hard cock sprung free a small gob of pre-cum splattered her face. Mom looked into my eyes as she swiped her finger over it and then stuck it in her mouth. My erection was now painful it was so hard. Mom quickly engulfed my stiffy. Her tongue swirled around the shaft as she descended. She cupped my balls in her hand. I was shaking, my mind gone. I was lost in the sensations she was creating in me. When a finger found my anus and pressed inward I moaned loudly and released my load in her mouth. I felt like I was going to never stop cumming. Mom swallowed it all, her mouth glued to my cock as she continued to bob her head up and down, sucking me dry. She slowly released my spent prick from her lips. I looked into her eyes as she hugged me around my waist.
Mom slowly got to her feet. I noticed her nipples looked hard as they poked through her dress. Her face was flushed and her eyes had this funny look. She leaned forward and kissed me. As our tongues dueled she let a tiny bit of my cum into my mouth. It wasn't bad. The kiss seemed to go on forever. Then it was over and Mom was leading me over to the couch. She sat down on the edge and pulled me down until I was kneeling in front of her. Our kiss resumed and this time I let my hands roam over her body. I wasn't sure how long this would last so I was going to try as much as I could before we finished. My right hand rubbed her hip and ass while my left cupped her breast. I was kissing the side of her neck and just behind her ear. She moaned and slid forward. I kept this up until she stopped me.
"I need you to do something for me." She gasped, her hips still moving in tight little circles on the couch cushion. "I need you to kiss Mommy's pussy, baby." Even as she said it she was placing her hand behind my head and gently guiding my head lower. She stopped long enough to gather the bottom of her dress and raise it above her hips. When she scooted forward and opened her thighs I got a great view of her panty covered crotch. I was surprised at how much hair was pushing out the sides of her beige nylon panty. The part covering her pussy was sodden and partially buried between her lips. I touched a finger to it and I could feel her slippery wet heat.