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Pleasing Rebecca

"Learning about Sex"

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Famous Story
My name is Tim and I am a nerdy eighteen year old guy. I have never had sex. I am just a very wimpy guy. I'm not very tall. I'm only five foot four inches tall, and I'm very thin. People in school would always call me a string bean. I'm very unsure of myself around women, because I've never been with one. I'm not muscular, but I do run to stay in shape.

I'll be going to college in September, to get my degree in finance. I'm very smart and have a real good sense with numbers. I was in the top of my class in high school. I received a full scholarship to the college that I'll be attending in the fall. I just graduated high school, and had celebrated my eighteenth birthday. My parents took me out for a nice dinner. They also bought me a new laptop and printer. I was very excited.

I fantasize about having sex with a woman, but I've yet to do that. I'm always jerking off and reading nude magazines. I tend to jerk off many times in the day. I even watch a lot of porn on my computer. I guess I'm just your average eighteen year old. Well maybe not average, since I'm a virgin.

Lately, I've been really thinking about our new neighbor, Rebecca. She and her husband moved in next door. Her husband is in the army. He's overseas on a tour of duty. Rebecca is seven months pregnant.

Rebecca is a knock out. She's tall and has beautiful long legs. She probably weighs around a hundred and twenty pounds. When she isn't pregnant, I'd say she is a C cup, but since becoming pregnant, I'd say she is a D cup. I think she's probably a size seven in her pants. She's a hot mama for sure. Rebecca, has long brown hair and she's got blue eyes. She has the most beautiful eyelashes you've ever seen. When she puts mascara on they just look amazing.

Recently, my mother has been sending me over to help her unpack her things. Rebecca, sometimes will be in very revealing clothes. I think she wants to get a rise out of me. I try not to stare at her, but she has enormous breasts, because she's pregnant, and the milk engorges her breasts.

The last time I was over her house, she was wearing a maternity dress. She'd given me a job of hanging pictures in her family room. The next thing I noticed, she removed her dress and was sitting in the chair in her panties. Rebecca was rubbing and massaging her enormous breasts.

I didn't know what to do and I became flustered. She was squeezing her breasts together and playing with her nipples.

“Timmy, I want you to suck my nipples. As you know, I'm pregnant. It would really turn me on if you did this for me.”

I didn't know what to think, but I agreed as I really wanted to taste those huge jugs. We moved to the couch, and Rebecca was sprawled out on the couch. I nestled up to her and started to touch her breasts. My mouth slowly began to suck on her nipples, and sure enough her breast milk came out. We were on the couch for a long time.

Rebecca was very turned on, and she was almost in a euphoric state. Her fingers were in her panties and she was fingering herself. My lips were just sucking and enjoying all of her milk. She did allow me to play with her breasts. I'd suck one nipple, and then I would rub and massage her other breast.

Rebecca was working her fingers deep in her pussy. She was turned on by me sucking her breast milk out of her heaving breasts. She was finger fucking her wet vagina faster and faster. I continued to suck and enjoy her breast milk that was coming out. Rebecca let out a scream and began to orgasm. Her fingers were soaking wet.

“Timmy, lick my fingers and enjoy my come!”

I did what she wanted. I was in complete fantasy mode. Rebecca was letting me suck her breast milk, and now I got to suck her fingers of all her cum.

“Timmy, let me jerk off your cock. Come over here!”

I took down my pants and Rebecca got to work. Her fingers had a firm grip on my six inch cock. She moved her fingers up and down my shaft. Her fingers felt so good. Her other hand fondled my sagging balls. I was really enjoying this.

Rebecca’s hands worked fast up and down my rock hard cock. I didn't last too long and came in her hands. Rebecca licked her palm, of all my come and just smiled.

“Timmy, I want you to come over every day. I'll let you enjoy my breast milk and do other things with you.”

I smiled, and said that sounded like a wonderful idea. I was so freaking happy and got dressed and left.

The next day I'd gone over and Rebecca had on another maternity dress. This time she didn't give me anything to do. We just went straight to the couch and she took off all her clothes.

“Timmy, come over and let’s get comfortable on the couch. Go on and enjoy my breasts.”

I did as she said and got busy enjoying her sweet breast milk. I've got to tell you, Rebecca is just about the prettiest woman I've ever seen. My dick was getting harder by the minute. The more I sucked on her breast, the more turned on I was becoming. This time Rebecca was playing with my hair and rubbing my neck.

“Timmy, I know you've never been with a woman, but I'd like to let you finger my pussy." 

“Are you sure Rebecca? I'd just about die if you would let me finger you. You know I'm a virgin. I'm so horny and hot for you. I'd love if you would teach me how to please a woman.”

“Okay, Timmy I’m going to spread my legs and I just want you to place your fingers inside my pussy.

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I'll even allow you to lick my pussy. Go on dear.”

Well, I didn't need another invitation. I was so excited that I got in between her legs, and I got to work. I slid my finger into Rebecca’s warm snatch and started to finger her. It was like the best thing, I ever felt. I guess I was doing a good job because she started to moan.

“Go on Timmy replace your fingers with your tongue. Just explore my cunt with your tongue. Brush your tongue against my clit. Then just put your tongue in and out of my pussy.”

Rebecca pointed to her clit, and I just worked my tongue all around it. She spread her legs further, and was enjoying what I was doing to her. I was so freaking horny. My cock was as hard as a rock, in my pants.

I slid my tongue inside of her pussy, and began to fuck her with my tongue. Rebecca started to buck wildly, while she was grinding on my face. I was just about dying. Her cunt was as delicious as a peach. I read that pussies do taste like peaches, and hers was as ripe as one.

I licked her pussy for a good amount of time. She was very excited and squeezing her big tits. Her milk was coming out as she played with herself.

I then went back up to her, to suck at her tits and enjoy her sweet milk. She really was getting off on the pussy licking, but she definitely liked me sucking on her tits.

“Timmy, please go back and lick my pussy. I'm going to be coming dear.”

With that Rebecca screamed and had an orgasm. Her pussy was dripping her sweet juices, and I was licking them up, like a kitten drinking milk. It was the best thing I ever tasted in my life. Her cunt was soaking wet and at that minute, I was the guy who was going to be cleaning her up.

“Timmy, I want to suck your cock now. Would you like that dear?”

“Rebecca, I would absolutely love it. I have never enjoyed a blow job before.”

“Okay, dear take off your pants and underwear, and I will get to work.”

Well, I did as she said. I was fully erect, and Rebecca got on her knees, and she put her cock into her mouth. I was just about going to die. Here is this gorgeous women who is going to give me pleasure. Rebecca stroked my cock with her hand and swirled her tongue around the tip of my head. She was looking into my eyes and then slid my hard cock into her mouth.

Rebecca bobbed up and down over my virginal cock. She sucked, slurped, and gagged on my dick. It felt so good, like what I've been dreaming about my whole life. I stated to move my hips and face fuck her a little. I'd seen that in a porno movie. I held Rebecca’s hair so I could watch her suck on my cock. As good as this was feeling, I couldn't hang on. I came in Rebecca’s mouth. I shot my spunk down this gorgeous creature’s mouth. Rebecca swallowed all my come.

“Timmy, did you enjoy that love?”

“Holy fuck! Yes, I loved it. I can never thank you enough for giving me my first blow job.”

“I enjoyed it too. I am glad that I was your first.”

“Timmy, come back and sit with me on the couch. Please go on and suck my nipples again.”

She really seemed quite horny. The more I sucked her tits, the more she moaned. Her milk was so tasty and I really enjoyed drinking it for her. I guess I sucked her for another fifteen minutes. I was again becoming hard. I was so horny.

“Timmy, go upstairs in my medicine closet in my bathroom. There are some condoms there. I want to have sex with you.”

I looked at her and then I ran up the stairs to get the condom. I couldn't believe Rebecca was going to be letting me fuck her. I got the condom. I already knew how to put it on, as I had been practicing for years. I rolled the condom onto my prick.

Rebecca got on top of me, and slid my cock into her pussy. Rebecca was moving her gorgeous body up and down over my cock. I sat up and played and sucked on her huge tits. I was able to continue enjoying sucking her gorgeous tits, and extracting the breast milk, while Rebecca rocked her cunt over my hard cock.

She looked so gorgeous riding my pole. Her beautiful tits were swaying back and forth, and her hair was also moving. She looked like a god damn angel. I could not believe I was lucky enough to be having sex with this goddess. She was the most beautiful woman I ever saw, and now we were fucking.

“Rebecca, I'm coming.”

I was so fucking turned on. I blew my first load of come in my life. Rebecca gave me a kiss. I shoved my tongue into her mouth and enjoyed a kiss from this gorgeous woman. Rebecca got off my cock.

“Timmy, let me suck your cock and clean off the come.”

Rebecca again bobbed up and down over my cock. She cleaned off the come. I then pulled out of her mouth and got dressed.

“Rebecca, this was the best day of my life. I can never thank you enough. You made a horny virgin’s dream come true.”

“Timmy, it was my pleasure. Just come over every day and I will continue showing you how to please a woman. Maybe by the end of the summer you will be a master. Then you can start college and you'll be a stud.”

I left there that day the happiest guy in the world. The whole rest of the summer, I had sex with Rebecca. We fucked every day for three months. This was the best summer of my life. In September, I left to start college. I was now a very confident young man with a bright future. I often think about my time with Rebecca. I was her sexual muse. Rebecca had a son and ended up naming him Timothy.

Published 
Written by Mysteria27
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