A First For The Ages

I had been dating Rebecca for a few months and was really beginning to fall for her. She was smart, funny, beautiful, everything I wanted in a woman. She was tall and a little heavier than most but had all the right curves. Her chest was full and her ass and legs were firm from being athletic most her life. In my eye she was perfect. She was pure, innocent. She had chosen to wait on sex until she met the right person. I only hoped that that person would be me. Then one magical night I was lucky enough to be her first. That night would start a chain of events in my and her life that no one else would ever believe.

I arrived at Rebecca’s house just before dark to pick her up for our date. Our plans were to go out to eat and then catch a movie. I walked in and was greeted by her mother. Jean was a beautiful late 40’s MILF with long blond hair and an intoxicating smile. Though a little overweight, she was an older version of Rebecca, which made her that more attractive. I hugged Jean hello and then walked into the living room and shook Rebecca’s dad’s hand. Jean told me that Rebecca was finishing getting ready if I wanted to have a seat.

I sat down on the couch and made small talk with her parents until Rebecca entered the room. She was stunning. She was wearing a tight black button down shirt and a blue jean skirt that stopped about mid thigh. She had the shirt unbuttoned low enough to let her ample cleavage to spill out. I was speechless. She just smiled and walked over to me and hugged me and asked if I was ready to go.

“Sure thing. Good night everyone. We will be back after the movie.” I said as we headed to the door. We walked out to the car and I opened the passenger door for her as she sat down. As she sat down her skirt rode higher on her thigh and my cock began to stir. I walked around to the driver side and got in and we left. We made small talk on the way to the restaurant. We pulled up at the restaurant and walked inside and sat down to a fabulous meal.

While eating we talked and laughed and I couldn’t help but steal glances at her ample breasts. My mind began to wonder what it would feel like to hold her big tits in my hand. What would it be like to suck on her nipples and have her wrap her huge breasts around my cock. My dick began to stir again as I got lost in thought of her titty fucking my cock.

“Chance? Chance? Are you ok? Rebecca asked smiling at me.

“Yeah. Sorry, I was lost in thought.”

“What were you thinking about?”

“Nothing. Don’t worry about it.”

Rebecca just smiled, “Maybe later then.” She then winked at me and I just smiled.

We paid our check and left and headed to the movie theater. We paid for our ticket and went in and found our seats in the back. As the movie started we moved in close as I put my arm around her. We sat there enjoying the movie and enjoying the closeness. I felt her hand on my leg and my cock jumped. She sat watching the movie her hand rubbing up and down my thigh. My cock began to swell as her hand neared my crotch. I took a deep breath as her finger glided down the length of my penis. I looked at her startled at her new action. We had been dating for a while and had done nothing more than kissing. She looked at me and winked as she smiled and slid her hand back over my cock again.

I couldn’t believe it. She leaned back and started watching the movie again as she continued to gently run her hand up and down the length of my cock through my jeans. I sat back too and tried to focus on the movie but couldn’t. My dick was as hard as steel and was continuing to grow. I was overcome with desire as I felt myself getting closer and closer to cumming. She must have sensed this also because she gave my penis one last squeeze and removed her hand from my lap. She leaned in closer to me and kissed me on the cheek and whispered into my ear, “Later.”

I couldn’t believe what had just happened. Rebecca had essentially jacked me off during the movie. I couldn’t focus on the movie. I was horny and was hoping that she was going to help me release my frustrations. After the movie we walked back to the car and drove back to her house. We walked in and I sat down on the couch as she walked to the back to tell her parents she was home. She came back into the living room and sat down beside me and grabbed my arm and put it around her. We watched TV as I just held her in my arms.

A little while later she looked up at me, and as I turned to look at her she kissed me. As we kissed I eased my hand up to her neck and held her. Then I softly eased my hand down to her chest and started to gently caress her breasts. She began to moan as I slipped my hand inside the cup of her bra and began to pull and gently twist her hardening nipple. Her hand quickly found my cock as she began to rub me though my jeans again. I broke our kiss and started kissing her neck as I unbuttoned she shirt. She pulled my shirt off over my head as I pushed her shirt off of her shoulders.

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“Are you sure about this?” I asked as I gently caressed her huge breasts again.

“Yes, I’m sure. Just take it easy.” Rebecca assured me as I kissed her neck again.

She reached back and unhooked her bra as I kissed my way down her chest. I took her breast into my mouth and licked her nipple. She dropped her head back in pleasure and moaned and grabbed the back of my head and pushed me into her breast harder. I took the cue and began to suck on her nipple and then released and did the same to her other breast. She began to breathe heavier as I continued my work on her wondrous breasts.

Then I laid her back on the couch as I slipped off the couch and onto my knees. I kissed my way down her stomach as I spread her legs. She watched in quiet anticipation as I eased her skirt up to her hips. She smiled and bit her lip as I slid my tongue down the inside of her thigh to her panties. I could smell her sex through the thin material of her panties. I gently licked her pussy through her panties as she started breathing faster. I pulled her panties to the side as I looked at her pussy for the first time. It was hairy but manicured. Her lips were swollen and wet and anxiously awaiting my tongue.

I couldn’t wait any longer as I spread her pussy lips and began to lick her slick wet pussy. She rolled her eyes into her head and breathed deeply as I licked her pussy for the first time. I lapped up all of her juices as they began to flow from her freely. My tongue made contact with her clit making her moan out loudly. She realized she was louder than she had been and didn’t want to wake her parents. She took a pillow and bit down on it to keep from moaning as I continued my licking of her clit. Her gyrations became faster and I knew I was close to giving her an orgasm.

I eased my finger to her leaking pussy and rubbed her wetness. She began to moan into the pillow as I eased my finger into her to the knuckle. She was incredibly tight and my finger met quick resistance. I gently pushed forward as I continued my tongue assault. I quickly found a rhythm with my finger as she moved closer and closer to the edge. I sucked on her clit as I eased a second finger inside her and began to finger fuck her. She could take no more as she bit down hard on the pillow and clamped her legs around my head. Her pussy flooded my mouth with her cum. Her orgasm was long and hard. Her whole body tensed as she was brought to pleasures she had never experienced before.

As she released her grip around my head I eased up her body and kissed her ever so gently. She looked at me starry eyed and said, “Wow! That was incredible. If I would have known it felt that good I would have let you do that way before now.” I just laughed and said, “The night’s not over yet.”

She sat up with me and smiled a wicked smile and said, “No it’s not.” as she pushed me back onto the couch. She climbed on top of me and we started kissing. She broke our kiss and started kissing her way down my body. She kissed her way down my chest and down to my stomach where she stopped and unhooked my belt. Then she made quick work of my button and zipper as her hand fished into my boxers. She quickly pulled my cock free of my boxers and gasped.

“It’s so big. I have never really seen one up close before but this is definitely big.”

I just smiled and said “It’s yours. Do with it what you want.”

She grinned devilishly and started rubbing her hand up and down my rigid member. She stared into my eyes as she quickened her pace on my cock.

“Put it in your mouth and suck on it.” I encouraged.

“You mean like this?” she said as she slipped the head of my dick into her mouth and began to suck.

“Yes! That’s it! That’s good!” I said as I lay back enjoying her first blowjob.

She was a little hesitant at first as she began her first blowjob but quickly began to enjoy it as she entered more of my ready cock into her mouth. She started to suck harder and faster as she started stroking me too. The feeling was wonderful. She was sucking my cock with earnest and I knew I wouldn’t last much longer. I warned her “I’m about to cum. I’m about to CUMMM!!!” She lifted her mouth from my cock as it exploded. Cum gushed from my cock, splashing against her face. She jumped back as my cock continued to squirt rope after rope of cum all over my stomach.

“Holy shit! That surprised me!” Rebecca laughed as my cum dribble down her face to her chin. She wiped the cum from her face with her finger and fed it to her mouth. As she swallowed my cum she licked her lips. “Not bad! I think I like it.”

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I sat there relishing the moment when she said “Look at you all messy. I guess I’m going to have to clean you up.”She lowered her head to my stomach and licked all the cum from my body. As she finished licking up the last little bit she sat up and swallowed. She smiled at me and said “You have some more of that yummy cum for me?” as she started sliding her hand up and down my still rock hard cock.”

I leaned up and kissed her as I eased her onto her back on the floor. I stood up and took off the rest of my clothes as she lay on the floor nervously waiting for the next moment of the night. I dropped back to the floor and climbed between her legs and kissed her softly. “Are you ready?”

“Yes. I want you to be my first. Fuck me now.” She whispered lovingly.

I kissed her passionately as I lined my cock up at the entrance to her pussy. I broke our kiss and looked lovingly into her eyes as I eased the head of my dick into her hot hole. She grimaced in pain as I entered her so I held it there for a min to let her get use to my invading cock. When she was ready I entered her more, slowly pushing inch by inch of my cock into her until my cock bottomed out in her. I waited again until she was ready before I began to ease my cock out. Before I pulled it completely out I eased my dick all the way back in, in one smooth stroke.

She grunted as I hit the back of her pussy. I slowly pumped my cock into her tight pussy letting her pussy stretch to accommodate my girth. The pain started to subside as her moans began to change into moans of pleasure. I began to pick up the pace of my thrusts as she began moaning and breathing heavier.

I continued to slide my cock in and out of her pussy with quickened pace as she bit down on my lip as we kissed. Her orgasm was near and I was happy to bring her much needed pleasure. I slammed my cock into her hard and held it as her pussy gripped me tightly. Her cum soaked my cock as she exploded into a mind numbing orgasm. I just held her as come back down to earth.

“Are you ok?” I asked as she looked up at me lovingly.

“I am fine.”

I smiled and kissed her as I held her close. I rolled over onto my back, my cock never leaving her pussy. She sat up and started to rock up and down on my cock. I took advantage of the position and took her wonderful full breasts back into my hands. She sped up her humping as I groped her breasts and gently twisted her nipples. She bounded up and down the entire length of my cock as she neared the edge again. She bit her bottom lip to keep from screaming out as her third orgasm came. She fell to my chest, breathing heavy as she recovered.

She kissed me and said “Now it is your turn to cum again.”

She got off me and laid down beside me. “Fuck my titties.” I was shocked. “How’d you know that’s what I wanted?”

“Please! You’ve been staring at my tits all night. I knew you couldn’t wait for me to wrap these big tits around that big cock of yours. Now come on and fuck my titties!”

I wasted no time as I straddled her midsection and laid my cock between her breasts. It felt wonderful as she wrapped her tits around my cock. I started sliding my cock in and out of her ample cleavage. She leaned her head forward and took the head of my cock into her mouth and began sucking as I fucked her tits. The sensation was more than I could take. I pushed my cock into her mouth and exploded. She swallowed as fast as she could trying to drink all of my cum.

As my spent cock slipped from her mouth, a little cum dribbled down her cheek and onto the floor. I fell to the floor beside her and looked at her. Here lie the woman of my life, and she had just given me her innocence. I held her close to me as we kissed again. “That was wonderful. Thank you.” Rebecca said as we broke our kiss. “I am glad I could do that for you.”

“I love you.”

“I love you too.”

My life would change after that day. That was the beginning of some amazing new chapters in my life. One such chapter happened the very next day.

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Updated: April 16, 2018 — 3:18 AM

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