Connie and Friends
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Connie After 50 Years free porn video
This is a total fantasy based on a real person so her name is changed. It is also based on the fact that we did go to high school together and our lives did not cross paths until this year. Now we did not go to a reunion and we did not have sex, but the fantasies I had about her in my younger days did happen and they continue today. Don’t like the story? Planning to give it a thumbs down? Why not add a comment and tell me why you disliked it.
Connie knelt in front of me and within seconds my fly was open and my erection was in her hands. She looked up at me and kissed the tip of my cock and said, “I should have done this to you 50 years ago.” She opened her mouth and pressed the tip of my cock between her lips like she was going to suck a lolly pop. Her full lips were wet and warm and I nearly buckled at the knees with the erotic nature of this meeting.
Connie and I graduated in the same class in 1970, at the time she was the hottest girl in our class. You know the type, beautiful beyond description, cheer leader, class president, and dating the star football player. Me? Well I was a nerd that cared more about math and physics, and yes I carried a slide rule around on my belt and had 6 pens and pencils in a pocket protector. Yes, I was that guy you all laughed at and did not date during my high school years.
I spent most of my time in study of the classes that interested me. But like every adolescent I learned the joy of an orgasm and spent a fair amount of time fantasizing about what it would be like to be with a girl. And Connie lived rent free in my mind. Had she known the number of times I looked at a polaroid photograph I swiped out of her boyfriend’s gym locker she would have thought I was a real pervert.
I enlisted in the navy right out of high school because the draft was breathing down my neck. Connie, the vision in my head with nearly every jerk off session, went to the same college as that football player and I lost track of her from there. Fast forward to 2020 and the 50th class reunion was scheduled.
I had no plans to attend but while in my hometown for a visit one of my fellow nerds from back then encourage me to go. “All the cliques are gone, we all look our age, even the hotties aren’t so hot anymore.” So I went, I had no one to impress, I had been successful with an engineering company that assisted me in graduating from college after the navy. I had just retired and decided to get a motel instead of staying with my parents.
As I entered the reunion hall I didn’t recognize a single person. Well one I did, I saw Connie across the room and although she had aged like the rest of us, she still looked like that hot girl I had dreamed about all through high school and most of the way through the navy. I registered, shook hands with a few that reintroduced themselves, and listened to a couple, “I am so important and want to impress you,” guys.
This was starting to turn out just like high school. It seemed like people had this need to prove something. I grabbed a scotch and found a table that was empty and sat down to see what sort of comedy I could watch with the classmates acting important and strutting around like they owned the place.
“Larry, is that you Larry?” I heard behind me and a hand touched my shoulder. I turned and it was Connie with that smile that always made me hard. And it was doing the same thing now.
“Connie, I saw you across the room, I had no idea you would remember me.” I said as I extended a hand. She did not shake it but instead moved in for a hug and her huge boobs pressed against me before she kissed my cheek.
“Why wouldn’t I remember you?” she asked as she pulled out a chair and sat down, “You were the smartest guy I knew, how have you been, are you married, tell me everything.” She said in a long string of questions. The primary difference at that moment is that she didn’t want to preen for me and convince me how great her life was.
I filled her in on my career as an engineer and a messy divorce when I was 40.
“Oh I am sorry to hear that,” she said and placed her hand on mine.
“I guess a guy that works 60 hours a week forgets his wife has needs, she found herself a boy toy that was about 25 years old that would take care of her.” I said, “Can I get you a drink?”
“Sure, I’ll have what you are having?” she said picking up my glass and taking a sip, “oh I love scotch.”
From that point until dinner was finished Connie told me about her three marriages and divorces. “So what about you and that football player?” I asked.
“He turned out to be a real jerk. He got it in his head that I should have a threesome with him and a college cheerleader he brought to my dorm room.” Connie said with that look of anger that only comes from being deeply hurt.
I didn’t want to capitalize on her time but she said, “You better, you are the first guy here that has never hit on me and did not try to impress me so you could get in my pants tonight.” She looked me directly in the eye as saying this and I swear there was a “come fuck me look” behind those beautiful blue eyes. Connie’s face had lost its smooth flawless texture but she was still a knockout and her smile could melt the coldest heart.
I smiled and said, “I am a little more subtle than that,” and grinned before taking a sip of scotch to bolster my courage and calm my cock that was now at half-staff.
“Are you staying with your parents?” Connie asked.
“No I decided to give them a break, I had no idea how late this would go and they go to bed by 9:00 PM.”
“Let’s get out of here,” Connie said pulling at my hand, “this thing goes right in the toilet from here on out. There will be lots of bragging about past accomplishments and the big shots of the class making speeches and I think the surprise speaker is that bastard I followed to college.”
She stood and gave me a pouty smile as if she’d be hurt if I didn’t follow her. I took a big gulp of scotch as I stood, “So where should we go?” I asked.
“I want to go for a walk, let’s go to the old football field. It is a practice field now and no one goes there.” She pulled me to the door and pulled my self-adhesive name tag off, “we don’t need these now,” she said.
The practice field was across town from the hall we were in and I said, “My car or yours?”
“Yours,” she said as she grabbed my arm with hers pressing her big tit into my arm, “I walked over from my apartment to here.”
As we got to the car I opened the door for her. Connie stepped between the door and the car, turned, and pulled me to her. Our lips touched, it was like electricity passed through me. The girl I spent so much time fantasizing about was kissing me and it was no casual greeting kiss. I felt her lips part and took the signal and probed her with my tongue.
I felt Connie press her pelvis against me and there was no doubt she could feel my erection pressing against her. The kiss became passionate from the start and I felt her grind against me before breaking the kiss and saying, “I don’t think you are being very subtle with your approach now,” she said and I saw that smile the always had me wanting her.
“I realize that,” I said as my hand slid down her back and cupped her ass. “You have no idea how many times I imagined what it would be like to touch you and have you touch me back.”
“Really?” Connie asked, “Why didn’t you approach me?”
“I was a nerd, you were the best looking girl in high school and you had a boyfriend.” I said as I pulled her back to me and kissed her again. This time my hand moved up and I put my hand on the back of her head running my hands through her long silky hair. As a high schooler her hair was a dark brunette and now it was nearly white and instead of making her look old it made her all the more alluring.
Connie got in the car and as she did her little black dress rode up her thighs and she flashed me the tops of her stocking and garters. She looked up with a smile, “I hope you saw that because I intended you to see.”
I bent and ran my hand from her knee to the tops of her stockings. I felt her arch her back and spread her legs, I wanted to go higher but teased with, “I am going to be subtle,” I said as I stood and closed the door.
We drove to the practice field and got out in the inky darkness. There were faint white lines marking the field as we walked in the cool fall evening. “I loved football,” Connie said, “I loved being dressed in my cute little outfit and knowing that so many were looking at me. I think at times it made me feel like a slut. Does that shock you?” she asked.
“A little,” I said, “I used to watch you in your cheer leader outfit and many fantasies played through my mind, some not so nice.” I said and then turned to face her, “Does that shock you?”
“Yes, a little,” she said almost mocking my answer to her question. “I had no idea you even noticed me, it was probably just as well as I have this terrible luck with guys.”
We walked the length of the field and halfway to the end I felt her touch my hand, our fingers interlocked and I felt like I was a senior in high school again. I had butterflies in my stomach and I knew I wanted her and knew she was wanted me too. “When was your first date?” Connie asked.
“I was in my second year in the navy when I met the girl that would become my wife. Our romance started like a bolt of lightning, she made no apologies for being highly sexual.” I admitted thinking back to us having sex on the hood of my car on the first date. She hopped up on the fender of my 72 Mustang, spread her legs and pulled me between them. She wasn’t wearing panties and she had no hesitation in exposing my cock that sprang to life the moment she touched me.
“Penny for your thoughts,” Connie said as we reached the end of the field.
“I was just remembering how it felt to be so young and inexperienced, the first time I had sex was with my soon to be wife setting on the hood of my Mustang.” I said, “We were both overheated and it lasted about 3 minutes.” I grinned, “Are you cold?”
“Yes, can we go to your motel, I think we can last more than 3 minutes and be a whole lot more comfortable.” Connie said pulling me close to her and running her hand across my throbbing cock.
In the motel room Connie sucked my cock into her mouth and I could feel my balls hit her chin. I loved the feeling of it but wanted more than a blow job so before she got me going too far I pulled out and said, “I have something to show you.”
“You certainly do, let’s get naked,” She said as she stood and unzipped her little black dress and let it fall to the floor. She had on a matching black bra and panties with a black lace garter belt and thigh high stockings. “Well you need to catch up,” she said and unbuckled my belt and stripped my trouser off leaving my erection sticking out over the top of my briefs.
I finished stripping and pulled her to me, my erection sticking between her legs. Her skin was so soft to the touch, just as I always imagined it. Gone was the smooth flawless skin of youth, but I didn’t care. We stumbled to the bed and she pushed me onto my back and straddled me.
“I need your help,” she said as she dropped her hands on either side of my shoulders, “Will you do the honors and unhook me?”
My hands trembled, I was so close to seeing her naked, her picture came back to my mind and I wondered how she had changed. The bra clung to her tits even with the back unhooked. She sat up and seductively pulled it off, hiding her nipples like a stripper.
She smiled and I pulled her hands off revealing her tits. Her nipples were hard and sticking out as over a half inch long and more impressive as wide as they were long. I pulled her down and sucked a nipple into my mouth. “I take it that you like what you have in your mouth as much as I liked what I had in my mouth a minute ago? Too bad you couldn’t have seen them 50 years ago.”
I answered with a light bite of her nipple while I rolled the other with my thumb and forefinger. “I can’t imagine them being any more magnificent than they are from my current view point.” I said as she moaned in pleasure. Connie shifted around and ground her pussy against my cock. The nylon panty was soaking wet and I reach down and pulled it aside. “Oh yes,” she said and shifted her hairless pussy over my tip and slid onto my cock. “Fuck yeah Larry,” she hissed as she rocked her hips driving my cock in and out of her pussy.
“I promised we would last more than 3 minutes,” she said, “but damn you feel so good inside of me. Do you know how long since a man was inside of me?” I didn’t answer and thought, “it has been a long time since I was in a woman.”
She rocked her pelvis and I met her with a thrust, and her tits swung across my face as I saw her grimace and go stiff as her orgasm gripped her. Her pelvic muscles gripped me tightly and she sort of hummed her way through her orgasm. Just as she was coming down I felt the cramp and knew that another thrust or two and I would be there.
I looked up in her face, her eyes opened with that satisfied look that comes from an orgasm and she whispered, “now it is your turn,” and she rocked back and forth and I moaned as my cum shot into her over heated pussy. She was so wet before we started and I added my own wetness to her as I pulled her hips down hard against me and thrust as deep as I could.
The afterglow of sex is always such a tender time, or so I think. I loved lying next to Connie as she ran her fingers across my chest. Words didn’t seem to be needed as we lay in the darkened motel room. “I am happy you came,” she said.
“And I am happy you came too?” I said as I faced her with a smile, “And I am happy you were at the reunion.” I knew it was a lame play on of words but she smiled back.
“You said you had something to show me,” Connie said as she kissed my neck.
I rolled over and grabbed my appointment book that lay on the night stand. We moved up against the pillows as I unzipped it. “I am a bit embarrassed about this but could not be with you like this without showing it to you,” I said as I opened it and under a flap on the cover I pulled out the faded Polaroid photograph of her.
“Wow,” Connie said, “where did you get this? I have not seen this since high school.”
“I am a bit embarrassed to say I stole it from your boyfriend’s locker in gym class. He had it taped inside the door and would flash it around when he opened the door.” I said.
“That bastard, he said he wanted it for his own use and promised never to show it off.” Connie said as she took the picture from my hand. “So this was the root of a lot of fantasies?” she asked.
“Yes it was and now I don’t need the picture because we had what I fantasized about.” I said and finished, “you can have the picture back.”
“Nope,” Connie said, “it is yours, I am happy you have it, and now I will show you a little more of what you have been missing for 50 years.”
Connie knelt in front of me and within seconds my fly was open and my erection was in her hands. She looked up at me and kissed the tip of my cock and said, “I should have done this to you 50 years ago.” She opened her mouth and pressed the tip of my cock between her lips like she was going to suck a lolly pop. Her full lips were wet and warm and I nearly buckled at the knees with the erotic nature of this meeting.
Connie and I graduated in the same class in 1970, at the time she was the hottest girl in our class. You know the type, beautiful beyond description, cheer leader, class president, and dating the star football player. Me? Well I was a nerd that cared more about math and physics, and yes I carried a slide rule around on my belt and had 6 pens and pencils in a pocket protector. Yes, I was that guy you all laughed at and did not date during my high school years.
I spent most of my time in study of the classes that interested me. But like every adolescent I learned the joy of an orgasm and spent a fair amount of time fantasizing about what it would be like to be with a girl. And Connie lived rent free in my mind. Had she known the number of times I looked at a polaroid photograph I swiped out of her boyfriend’s gym locker she would have thought I was a real pervert.
I enlisted in the navy right out of high school because the draft was breathing down my neck. Connie, the vision in my head with nearly every jerk off session, went to the same college as that football player and I lost track of her from there. Fast forward to 2020 and the 50th class reunion was scheduled.
I had no plans to attend but while in my hometown for a visit one of my fellow nerds from back then encourage me to go. “All the cliques are gone, we all look our age, even the hotties aren’t so hot anymore.” So I went, I had no one to impress, I had been successful with an engineering company that assisted me in graduating from college after the navy. I had just retired and decided to get a motel instead of staying with my parents.
As I entered the reunion hall I didn’t recognize a single person. Well one I did, I saw Connie across the room and although she had aged like the rest of us, she still looked like that hot girl I had dreamed about all through high school and most of the way through the navy. I registered, shook hands with a few that reintroduced themselves, and listened to a couple, “I am so important and want to impress you,” guys.
This was starting to turn out just like high school. It seemed like people had this need to prove something. I grabbed a scotch and found a table that was empty and sat down to see what sort of comedy I could watch with the classmates acting important and strutting around like they owned the place.
“Larry, is that you Larry?” I heard behind me and a hand touched my shoulder. I turned and it was Connie with that smile that always made me hard. And it was doing the same thing now.
“Connie, I saw you across the room, I had no idea you would remember me.” I said as I extended a hand. She did not shake it but instead moved in for a hug and her huge boobs pressed against me before she kissed my cheek.
“Why wouldn’t I remember you?” she asked as she pulled out a chair and sat down, “You were the smartest guy I knew, how have you been, are you married, tell me everything.” She said in a long string of questions. The primary difference at that moment is that she didn’t want to preen for me and convince me how great her life was.
I filled her in on my career as an engineer and a messy divorce when I was 40.
“Oh I am sorry to hear that,” she said and placed her hand on mine.
“I guess a guy that works 60 hours a week forgets his wife has needs, she found herself a boy toy that was about 25 years old that would take care of her.” I said, “Can I get you a drink?”
“Sure, I’ll have what you are having?” she said picking up my glass and taking a sip, “oh I love scotch.”
From that point until dinner was finished Connie told me about her three marriages and divorces. “So what about you and that football player?” I asked.
“He turned out to be a real jerk. He got it in his head that I should have a threesome with him and a college cheerleader he brought to my dorm room.” Connie said with that look of anger that only comes from being deeply hurt.
I didn’t want to capitalize on her time but she said, “You better, you are the first guy here that has never hit on me and did not try to impress me so you could get in my pants tonight.” She looked me directly in the eye as saying this and I swear there was a “come fuck me look” behind those beautiful blue eyes. Connie’s face had lost its smooth flawless texture but she was still a knockout and her smile could melt the coldest heart.
I smiled and said, “I am a little more subtle than that,” and grinned before taking a sip of scotch to bolster my courage and calm my cock that was now at half-staff.
“Are you staying with your parents?” Connie asked.
“No I decided to give them a break, I had no idea how late this would go and they go to bed by 9:00 PM.”
“Let’s get out of here,” Connie said pulling at my hand, “this thing goes right in the toilet from here on out. There will be lots of bragging about past accomplishments and the big shots of the class making speeches and I think the surprise speaker is that bastard I followed to college.”
She stood and gave me a pouty smile as if she’d be hurt if I didn’t follow her. I took a big gulp of scotch as I stood, “So where should we go?” I asked.
“I want to go for a walk, let’s go to the old football field. It is a practice field now and no one goes there.” She pulled me to the door and pulled my self-adhesive name tag off, “we don’t need these now,” she said.
The practice field was across town from the hall we were in and I said, “My car or yours?”
“Yours,” she said as she grabbed my arm with hers pressing her big tit into my arm, “I walked over from my apartment to here.”
As we got to the car I opened the door for her. Connie stepped between the door and the car, turned, and pulled me to her. Our lips touched, it was like electricity passed through me. The girl I spent so much time fantasizing about was kissing me and it was no casual greeting kiss. I felt her lips part and took the signal and probed her with my tongue.
I felt Connie press her pelvis against me and there was no doubt she could feel my erection pressing against her. The kiss became passionate from the start and I felt her grind against me before breaking the kiss and saying, “I don’t think you are being very subtle with your approach now,” she said and I saw that smile the always had me wanting her.
“I realize that,” I said as my hand slid down her back and cupped her ass. “You have no idea how many times I imagined what it would be like to touch you and have you touch me back.”
“Really?” Connie asked, “Why didn’t you approach me?”
“I was a nerd, you were the best looking girl in high school and you had a boyfriend.” I said as I pulled her back to me and kissed her again. This time my hand moved up and I put my hand on the back of her head running my hands through her long silky hair. As a high schooler her hair was a dark brunette and now it was nearly white and instead of making her look old it made her all the more alluring.
Connie got in the car and as she did her little black dress rode up her thighs and she flashed me the tops of her stocking and garters. She looked up with a smile, “I hope you saw that because I intended you to see.”
I bent and ran my hand from her knee to the tops of her stockings. I felt her arch her back and spread her legs, I wanted to go higher but teased with, “I am going to be subtle,” I said as I stood and closed the door.
We drove to the practice field and got out in the inky darkness. There were faint white lines marking the field as we walked in the cool fall evening. “I loved football,” Connie said, “I loved being dressed in my cute little outfit and knowing that so many were looking at me. I think at times it made me feel like a slut. Does that shock you?” she asked.
“A little,” I said, “I used to watch you in your cheer leader outfit and many fantasies played through my mind, some not so nice.” I said and then turned to face her, “Does that shock you?”
“Yes, a little,” she said almost mocking my answer to her question. “I had no idea you even noticed me, it was probably just as well as I have this terrible luck with guys.”
We walked the length of the field and halfway to the end I felt her touch my hand, our fingers interlocked and I felt like I was a senior in high school again. I had butterflies in my stomach and I knew I wanted her and knew she was wanted me too. “When was your first date?” Connie asked.
“I was in my second year in the navy when I met the girl that would become my wife. Our romance started like a bolt of lightning, she made no apologies for being highly sexual.” I admitted thinking back to us having sex on the hood of my car on the first date. She hopped up on the fender of my 72 Mustang, spread her legs and pulled me between them. She wasn’t wearing panties and she had no hesitation in exposing my cock that sprang to life the moment she touched me.
“Penny for your thoughts,” Connie said as we reached the end of the field.
“I was just remembering how it felt to be so young and inexperienced, the first time I had sex was with my soon to be wife setting on the hood of my Mustang.” I said, “We were both overheated and it lasted about 3 minutes.” I grinned, “Are you cold?”
“Yes, can we go to your motel, I think we can last more than 3 minutes and be a whole lot more comfortable.” Connie said pulling me close to her and running her hand across my throbbing cock.
In the motel room Connie sucked my cock into her mouth and I could feel my balls hit her chin. I loved the feeling of it but wanted more than a blow job so before she got me going too far I pulled out and said, “I have something to show you.”
“You certainly do, let’s get naked,” She said as she stood and unzipped her little black dress and let it fall to the floor. She had on a matching black bra and panties with a black lace garter belt and thigh high stockings. “Well you need to catch up,” she said and unbuckled my belt and stripped my trouser off leaving my erection sticking out over the top of my briefs.
I finished stripping and pulled her to me, my erection sticking between her legs. Her skin was so soft to the touch, just as I always imagined it. Gone was the smooth flawless skin of youth, but I didn’t care. We stumbled to the bed and she pushed me onto my back and straddled me.
“I need your help,” she said as she dropped her hands on either side of my shoulders, “Will you do the honors and unhook me?”
My hands trembled, I was so close to seeing her naked, her picture came back to my mind and I wondered how she had changed. The bra clung to her tits even with the back unhooked. She sat up and seductively pulled it off, hiding her nipples like a stripper.
She smiled and I pulled her hands off revealing her tits. Her nipples were hard and sticking out as over a half inch long and more impressive as wide as they were long. I pulled her down and sucked a nipple into my mouth. “I take it that you like what you have in your mouth as much as I liked what I had in my mouth a minute ago? Too bad you couldn’t have seen them 50 years ago.”
I answered with a light bite of her nipple while I rolled the other with my thumb and forefinger. “I can’t imagine them being any more magnificent than they are from my current view point.” I said as she moaned in pleasure. Connie shifted around and ground her pussy against my cock. The nylon panty was soaking wet and I reach down and pulled it aside. “Oh yes,” she said and shifted her hairless pussy over my tip and slid onto my cock. “Fuck yeah Larry,” she hissed as she rocked her hips driving my cock in and out of her pussy.
“I promised we would last more than 3 minutes,” she said, “but damn you feel so good inside of me. Do you know how long since a man was inside of me?” I didn’t answer and thought, “it has been a long time since I was in a woman.”
She rocked her pelvis and I met her with a thrust, and her tits swung across my face as I saw her grimace and go stiff as her orgasm gripped her. Her pelvic muscles gripped me tightly and she sort of hummed her way through her orgasm. Just as she was coming down I felt the cramp and knew that another thrust or two and I would be there.
I looked up in her face, her eyes opened with that satisfied look that comes from an orgasm and she whispered, “now it is your turn,” and she rocked back and forth and I moaned as my cum shot into her over heated pussy. She was so wet before we started and I added my own wetness to her as I pulled her hips down hard against me and thrust as deep as I could.
The afterglow of sex is always such a tender time, or so I think. I loved lying next to Connie as she ran her fingers across my chest. Words didn’t seem to be needed as we lay in the darkened motel room. “I am happy you came,” she said.
“And I am happy you came too?” I said as I faced her with a smile, “And I am happy you were at the reunion.” I knew it was a lame play on of words but she smiled back.
“You said you had something to show me,” Connie said as she kissed my neck.
I rolled over and grabbed my appointment book that lay on the night stand. We moved up against the pillows as I unzipped it. “I am a bit embarrassed about this but could not be with you like this without showing it to you,” I said as I opened it and under a flap on the cover I pulled out the faded Polaroid photograph of her.
“Wow,” Connie said, “where did you get this? I have not seen this since high school.”
“I am a bit embarrassed to say I stole it from your boyfriend’s locker in gym class. He had it taped inside the door and would flash it around when he opened the door.” I said.
“That bastard, he said he wanted it for his own use and promised never to show it off.” Connie said as she took the picture from my hand. “So this was the root of a lot of fantasies?” she asked.
“Yes it was and now I don’t need the picture because we had what I fantasized about.” I said and finished, “you can have the picture back.”
“Nope,” Connie said, “it is yours, I am happy you have it, and now I will show you a little more of what you have been missing for 50 years.”
Cayleigh
- 17.05.2021
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