Second Chance At Love
Copyright© 2006 by Douglas Fox
Part 5: Jenny
Erotica Sex Story: Part 5: Jenny - 16 year old Will Henry takes his girlfriend Abby's virginity. His sexual prowess leads Abby to ask about his sexual history. Will tells the story from losing his virginity to his first love in the Canadian wilderness on a camping trip with older youth, to dating a nymphomaniac, to popping the cherries of some girlfriends as well as assorted other sexual escapades in the past two years.
Caution: This Erotica Sex Story contains strong sexual content, including mt/ft Teenagers Consensual First Safe Sex Oral Sex Anal Sex Masturbation Sex Toys Pregnancy Slow
The next morning, when I got on the school bus, there weren't very many seats empty. I sat down with Jenny Trimble. Jenny is in eighth grade. She is short, about 5'-1". She is starting to develops some very nice curves, but she was just starting to develop. We talked on the way to school. Jenny had a nice personality. She was fun to talk to. I started to think that it might be fun to go on a date with her.
I thought about it during the school day. I decided to ask her on the way home from school. I purposely waited by the front door of the school so I could "casually" run into Jenny when she came out. I fell in step with Jenny as we walked to our bus.
When Jenny sat down on an empty seat, I asked, "May I sit with you?"
Jenny smiled at me. "Sure, Will. Have a seat."
"How was school today?" I asked.
"It was OK."
"Jenny, I was wondering. Would you like to go to a movie with me on Friday night?"
"Sure. That sounds like fun Will."
"I'll pick you up around 6:30, OK?"
Jenny and I sat together on the bus every morning and evening that week. We talked about school. We talked about the weather. Just talked. Jenny was fun to talk with. On Friday afternoon, I reminded Jenny that I would pick her up around 6:30.
I fussed with what I was going to wear. Finally I chose my clothes and got dressed. My mom drove me the two blocks to Jenny's house. She waited in the car while I went inside to meet Jenny and her parents. They asked me a few questions, like what time we were coming home. I promised that Jenny would be home by 10 o'clock.
We walked out to my mom's car. After we were in, mom drove us to the movie theater. I bought us tickets and went into our theater. We sat near the back. About five minutes into the movie, I stretched and put my arm around Jenny's shoulders. A few minutes later I slid a little closer to Jenny and held her tight against me. Jenny laid her head against my chest. We sat this way for fifteen or twenty minutes.
I decided to try for more. I "casually" let my hand slip down her chest. My hand ended up on her right breast. I didn't move it. I waited to see how Jenny was going to react. Jenny cuddled up to me. Jenny put her hand on my knee and squeezed it.
I took that as my signal. I started to caress her breast. Jenny was moaning quietly and rubbing my leg. Jenny's breasts were small, less than a handful for me. Jenny's reaction told me that they were just as sensitive as my past girlfriend's breasts. I kept rubbing them.
After a few minutes, I asked Jenny, "May I kiss you?"
Jenny answered hesitantly, "I... guess so." Jenny turned her head up and looked at me. I leaned down and kissed Jenny on the lips. When our lips met, I opened my lips a little and slipped my tongue out. I licked along Jenny's lips. Then I pushed the tip of my tongue against her lips, seeking entry. Finally Jenny opened her lips a little. I pushed my tongue into her mouth. I met the tip of her tongue. I slid mine along hers. I felt around the insides of her mouth. Her tongue was responding. She pushed back, wrestling my tongue with hers.
We paused for a breath. "Wow, Will. That was great. Let's keep doing this."
"I'm glad you liked it." Jenny and I went back to French kissing. I don't know how the movie ended. Jenny and I spent the rest of the evening kissing and rubbing each other. When the movie ended we left the theater reluctantly. We didn't want to stop making out. We waited outside for my mom to pick us up.
I asked, "Do you want to get together again?"
"Sure."
"How about if we hang out after school on Tuesday?"
"Why not Monday?"
"I have to do homework then. I have scouts in the evening."
"OK, Will. I'm looking forward to getting together again." I gave Jenny a short kiss just as my mom pulled up. I blushed when I noticed my mom saw us.
Jenny and I sat together on Monday and Tuesday on the bus. Tuesday after school Jenny got off at my bus stop instead of staying on the bus until her stop, the next one on the route. We walked together to my house. We made a strange sight. I was 6'-2" and Jenny was 5'-1" She came about to my nipples. Jenny's build is best described as petite. I'm thin, but not skinny. My weight training has put muscle on my lean frame. We held hands as we went.
I got cookies and Cokes for us when we got to my house. We went to the family room to watch TV. We settled in and ate our snack. When we finished, I asked, "Jenny, would you like to pick up where we stopped on Friday night?"
"I guess Will." I leaned down and kissed Jenny on the lips. Soon we were making out with passion. I rubbed and caressed her tits as we kissed. Jenny was moaning from the stimulation. We made out for almost a half hour. We didn't stop until a new program came on the TV.
I asked, "Jenny, can I see your tits? They feel so wonderful when I feel them."
"Your touching me there is making me so excited. But I'm not supposed to do that with a boy."
"It'll feel wonderful if I can rub your tits when they are bare." I rubbed her right tit through her shirt. I started to push the bottom of her blouse up, trying to get my hand up under it. I kissed Jenny, trying to stimulate her with my tongue in her mouth. I kept sliding my hand up under her blouse as we kissed. Jenny moaned into my open mouth as we kissed. My hand finally reached her bra. I slipped my hand under it and felt a bare tit.
"Will, stop that. I shouldn't let you do... ooohhhh..."
"Please, I want to see them Jenny. Please???" I pleaded. I continued rubbing her tit under her blouse.
I kissed Jenny a little more while I rubbed her tits. I used one hand to unbutton Jenny's blouse. I had half the buttons undone before she realized what I was doing.
"Stop that Will!"
"Please Jenny, I want to see your tits. They feel so nice. I just want to see them."
"I guess. But just look, OK?"
"YES! Absolutely! I'll just look at them." I unbuttoned the rest of Jenny's buttons. Jenny pulled her blouse off. Then she removed her bra. "Oh Jenny. You look beautiful." I leaned in over Jenny pressing her back against the couch as I kissed her. I pressed my body against hers. I rubbed my body up and down against her chest as we kissed. I tried to use my tongue to turn Jenny on. I slid one hand between us and played with her nipple as we kissed.
When we stopped for breath, I leaned back to look at Jenny. She was flushed. "Jenny may I feel your tits?" I started reaching for them before she could answer.
"Will, I'm not sure if..." I rubbed her nipple. "Ooooohhh... Will... I don't think... " I brought my other hand up and caressed both breasts at the same time. "Ooohhh... Will... Should we... do... ooohhh... Will... don't stop. Ooohhhh..."
I kissed Jenny on the lips while I rubbed her tits. I kissed my way down from her lips to her neck and then down her chest. I was heading for her left tit. I kissed her tit when I reached it. I sucked her nipple into my mouth. I sucked for a few seconds and then twirled my tongue around her nipple. I let go of her nipple and kissed in a ring around her nipple. I worked on her other tit with my left hand. Jenny was moaning and panting.
After five minutes of working on her tits, I kissed my way back up her chest to her mouth. I worked my tongue into her mouth. I lay my 6'-2" body over Jenny, pressing it against her body. My cock was erect. It was pressing Jenny in the thigh. I tried for third base. I pushed my hand gently into Jenny's pants while I kissed her. I slid it down until I was holding my hand over her the crotch of her panties. They were soaked.
Jenny sat up suddenly pushing me away. "Will, NO! I don't want to do that."
I pulled my hand out of her pants. "I'm sorry Jenny. Please forgive me. It's just that you're so beautiful. You get me so worked up."
"We can kiss. But nothing below the waist, OK?"
"I promise." I concentrated on feeling up her tits and on French kissing. Jenny and I kept each other in a state of arousal for another forty minutes. When the TV changed programs, I realized it was 4:30. "Jenny, my mom will be home in about thirty minutes. We better get dressed. I don't want to get in trouble for being home alone with a girl."
"OK, I probably better get home. My mom is going to wonder where I am too."
I walked Jenny to the door and gave her a kiss before she got to the door. "Do you want to get together after school tomorrow?"
"Sure. I'll see you on the bus tomorrow." She kissed me before she left.
I went straight to my room, closed the door and stripped. My cock was so hard. Jenny had me so horny I was ready to explode. I grabbed some lotion and spread it on my cock. I jerked off. My sperm fired, the first spurts landing on my neck. I usually didn't shoot this far.
On Wednesday morning Jenny greeted me with a big smile when I sat down beside her on the bus. I gave her a quick peck on the cheek. Mrs. Shirk was really strict. I didn't want to get written up and sent to the office. The real kiss would wait until we got inside the school building.
When we got off the bus and walked into the building, I hugged Jenny and gave her a deep fervent kiss. She headed one direction to the middle school wing of the building while I headed for the senior high side.
Jenny and I sat together on the way home. When the bus dropped us off, we walked to my house holding hands. We headed for the family room as soon as we got home. I turned on the TV. Jenny sat down on the couch and I sat beside her. We started kissing immediately. Today Jenny was pressing her tongue into my mouth just as often as mine reached into hers. I rubbed her tits as we kissed.
After five minutes, I asked, "Jenny can I see your tits again?" I rubbed her tits while I waited for an answer.
"I guess so." Jenny finally answered quietly. I unbuttoned her blouse and pulled it out of her pants. She pulled it off and then removed her bra. "Are you going to take off your shirt too?"
I was pulling it off before she even finished the sentence. Jenny looked over my bare torso. "Wow Will. I didn't know you were so muscular. Do you work out?"
"Yes. I've been lifting weights since last summer." Jenny stroked her hands up and down my chest. I shuddered when she reached my nipples. She stroked them a few times.
"Jenny, let me feel your breasts." She lay back on the couch and I moved over her. I kissed her on the lips and then kissed my way down to her tits. I sucked on her nipples and caressed them as I licked. We kissed, licked and felt each other for a long time.
I decided to see if I could get Jenny to go further today. I slid my hand down and placed it on her crotch, but on top of her jeans. I continued Frenching her while I did this. Then I started to rub her pussy through her jeans. Jenny squirmed a little and moaned as I did this.
"Jenny, doesn't this feel good?"
"Yes Will, don't stop." I kept rubbing her crotch.
"It will feel even better if your jeans are out of the way. It will feel wonderful."
"Umm... I'm not sure Will." I rubbed harder. "Ohhhh..." I reached down with my other hand and unbuttoned her jeans and unzipped them. I kissed her tit and sucked on the nipple. I pushed my free hand between her jeans and her panties. Her panties were soaking wet.
I quickly rubbed my finger up and down along her outer lips. "Will, I don't know if I want..." I rubbed up and down again. I rubbed at the top of her crotch, trying to hit her clitoris. "I don't know... OOOHHHHH..." There it is. I kept rubbing the spot. "Ohhhh... Will... I don't know... OOOHHHHH..."
I kept stimulating her clit. "Will, keep doing that. It's wonderful."
"Let's take off your jeans. I can do a better job if they are out of the way." I rubbed her clit while she considered it.
Finally she said "OK" quietly. She lifted her hips up while I pulled her jeans off. Jenny lay back on the sofa, partly reclining. I moved in closer to her crotch, sitting on the floor between her legs. I continued rubbing her clit and pussy through her panties. By now they were dripping from her lubrication.
I slid a finger under her panties and stroked it up along her outer lips. I felt for her clitoris when I reached the top. I rubbed and stroked it when I found it. Jenny was wiggling and squirming from my stroking. She moaned every time I stroked her clit.
"Jenny, can I see your pussy?" I rubbed her clit quicker to help her decide. "It'll feel really good." I promised.
"If I take them off, we can't have sex, OK? You have to keep your pants on."
"Absolutely. I wouldn't do anything you didn't want to do. I promise." I pulled at the top of her panties. She lifted her hips so I could take them off.
I rubbed her clit some more while I looked at Jenny. Her outer lips were puffy and red. They were leaking copious amounts of lubrication. Jenny had a sparse patch of blond hair over her pussy. The light color of her hair combined with the sparseness of it made her look younger than her thirteen years.
I decided it was time to bring up the heavy artillery. I bent down and licked up and down her pussy. "Oh my God. Will what are you doing?"
I didn't answer with words. I licked around her clit, teasing it. "Ooohhhh... Will..." I circled it a few more times with my tongue and then sucked it into my mouth. "Aahhhhh... Wwww... illlll..." Jenny was bucking and jerking now. She was almost there. I licked and sucked her clit. I pushed my finger into her pussy an inch. Jenny was tighter than any girl I had felt before. I pushed my finger in deeper while I teased her clit with my tongue.
Jenny screamed, "Aaaaaeeeiiii..." as she orgasmed. Her pussy squeezed and gripped my finger while her hips bucked up and down on the couch. Finally she collapsed in a heap in the couch. Jenny was panting.
"Did you enjoy this Jenny?" I looked at her prostrate body. She started to rouse herself.
"Will, I didn't know I could have an orgasm like that. That was fantastic." I stroked her clit again. "Will, please stop that. It's too sensitive now."
"Oh, I'm sorry." I sat down on the floor and stroked my crotch, trying to relieve some of the pressure in my balls. Jenny looked at me rubbing my crotch.
My erection was obvious by the way it pushed out my pants. "Will, does it hurt?"
"Not exactly hurt. But I really need to cum. If I don't cum, then it will hurt."
"Will, can I see your thing?"
I knew I had Jenny hooked. "You can, but only if you call it by a proper name. It's my penis, cock, dick or prick. It isn't a thing!"
"Will, may I see your penis?"
"OK" I unzipped my pants and pulled them off. I kept my boxers on. I didn't want to freak Jenny out.
I pulled my cock out through the slit in my boxers. It stood about six inches long. The head of it was reddish purple. Jenny stared at it.
"I didn't think your thing, uh your penis, would be so big. Can I touch it?"
"OK. Be gentle." Jenny reached out and touched the tip. She rubbed her finger in the precum that was leaking out of my cock. Then Jenny gently, almost daintily wrapped her hand around my cock.
"The top is soft, but the inside is hard. I don't know how something so big could fit in my pussy."
"My cock isn't really that big. It's average sized. At least for my age. Cocks have been fitting in pussies for thousands of years. I'm sure that a cock will fit in your pussy when you want it too."
"I guess." Jenny said dubiously.
"Can you hold onto my cock and stroke your hand up and down?" Jenny moved her hand up and down, but she was holding it too loose.
"Hold it a little tighter." She squeezed too hard.
"Owww. Not that hard! Let me show you how I do it." Jenny let go of my cock. I wrapped my hand around it and started to stroke. I didn't take long to climax. I shot sperm about three feet. The first spurt landed on Jenny's stomach. The second spurt landed on her thigh. The rest spurted and dribbled out on the floor.
"Wow. That was something Will. Does it always go that far?"
"No. It only goes that far when I'm with a beautiful girl who has me horny."
I put my rapidly shriveling cock back inside my boxers. I used Kleenex to wipe up the cum on Jenny and on the floor. Jenny and I got back on the couch and cuddled together. We kissed for a few minutes.
"Will, what is it like to have sex?"
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