Where it happened: At home
Langauge: English
Sex: Male
Rating: 5
Category: Straight
My first time was with the daughter of my divorced mom’s best friend, Trish. Trish was hot in her own right, and as a young teen, I had fantasized plenty about her. Trish had a physical feature that arouses me to this day: small tits. I’m not sure why, but I certainly was different than my classmates in that regard. Somehow, small breasts were, and are, erotic to me.
Her daughter, Molly, was only thirteen, but was beautiful just like her mother. Like her mother, her tiny breasts had my attention. Fortunately for me, she dressed such that I could sometimes catch brief glimpses of her little bras, and if I positioned myself just right, I could occasionally catch sight of her little nipples as her bra would pull away from her chest.
One evening, my mom and Trish went out for dinner with some friends and left Molly and me together. I was amazed at the opportunity, but I had no idea how to use it to get to know Molly better. I wasn’t even sure if Molly had any thoughts about me at all.
As soon as the door closed behind mom and Trish, I learned just how wonderful this night was going to be. Almost at once, quiet, shy Molly turned into a mischievous tiger! “Let’s explore,” she said. She grabbed me by the hand and yanked me with her, heading to my mom’s bedroom. “My mom has lots of fun toys in her room,” she giggled, “Let’s see what your mom has to offer.” I had no idea what she was talking about, but entering a bedroom with my boy crush holding my hand was a no-brainer.
She went straight for my mom’s nightstand and started opening drawers. “Aha!” she cried, “Just as I figured!” In her hand was a purple thing. It didn’t make much sense to me, but I was intrigued. “What’s that?” I asked. “Well, silly boy,” she said with a grin, ” This is what women use to make themselves feel good.” I’ve watched my mom use it in her bed when she didn’t know that I was watching.”
She paused and looked me in the eyes. “Wait in your room until I call for you, I’ll have a nice surprise.” My head spinning, I turned to leave. He pulled on my shirt as I was walking out and said, “Wait.” She reached up and gave me a kiss on the lips. “There, that should get you going.” I was in awe.
I went into my room. My young cock was rock hard and I was embarrassed thinking about how I was going to conceal it. More importantly, however, I was trying to guess what surprise i was going to enjoy.
I heard water running. I heard drawers opening and closing. Then, about 15 minutes later I heard her voice. “Tommy,” she said, “come on in.”
I slowly pushed open the door. The only light was the light from the bathroom that cast a nice glow around the room. There on my mom’s bed was Molly. She had changed into my mom’s negligee with that purple thing in her hand. I could see the outline of her black bra underneath the lacy material and I was going crazy with boy lust.
“Come over here, silly,” she said, “I want you to see how your mom spends some of her alone time. I walked over to the side of the bed. My cock was so hard it hurt. I sat down on the edge of the bed. With that she pushed a button on the purple thing and it started to make a buzzing sound. She leaned back on the bed and slowly lowered the vibrator across her breasts, down her stomach, and to the area between her legs. “Oooh,” she cooed. “This is what my mom does.” She hiked up the negligee to reveal her little black panties. She worked the toy around her crotch and slowly began to writhe.
“Take your clothes off Tom.” “I want to see you and play with you too.”
I stood up and stripped. At this point I didn’t mind that my cock was erect. I climbed next to her on the bed. I kissed her clumsily on the lips. I felt her little tongue go in my mouth and I was startled. Soon, however, I was comfortable and so lost in lust that nothing mattered.
She put the toy down and sat up in bed. She then lifted the oversized lacy top off of her body leaving her in nothing more than a little black bra and cute panties. She then reached back and undid her bra. Once I realized what was going to happen, I almost passed out. I was mesmerized. I watched as the firm cups of her bra slid off her body, and finally, revealed her tiny breasts to me. She reached up and held one in her little hand. “Kiss it,” she whispered. I did. I leaned into her and touched my lips to the silky smooth freshness of her breast bud. I followed that touch up with a kiss to her nipple. It felt firm on my tongue. I looked up and into her eyes.
“I have a surprise for us,” she said playfully. “Come.”
She pulled me into my mom’s bathroom. The tub was filled and bubbly. She reached down and pulled off her panties and nearly jumped in the water. “Join me?” she asked? I stepped into the warm water. “Wash me,” she ordered as she handed me a washcloth.
After we bathed, and I explored every inch of her little body, we went to the bed. We kissed and fondled until our hearts content.Finally, we reached the point of no return. I positioned myself between her legs. Without much thought, and certainly without much skill. I lowered my cock towards her pussy. Thankfully she grabbed my cock and guided it to her little pussy. She held her breath as she wiggled it between her small lips, and finally, I felt the amazing rush of warmth as it slid inside her. I remember my eyes being clenched closed as I seemed almost to blackout in emotions. As my body automatically began to thrust, I opened my eyes to see her tiny tits moving with her. Nipples hard and pointed to the sky. Her eyes were closed too. Soon, I could feel my body begin to build. I knew this was it. She moaned as my thrusts grew faster. I exploded. She squealed as I thrust deep. As the orgasm subsided, I fell over to her side.
We looked at each other. Our eyes wide open. We couldn’t help but giggle. “So this is what your mom is doing when she doesn’t know you’re watching?”
“Yeah,” she said. “Isn’t it amazing?”
We cleaned up, and put everything back the way we left it. When our moms came home we acted as if nothing had happened. When Molly left, she snuck a kiss.
I will never forget my first time. She was amazing. We have kept in contact over the years. Although we haven’t brought up that evening again, it still remains a piece of us. A bond that can never be broken.
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