Sherry got fucked by the Shemale hairdresser Shemale Sex Stories
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Who Knew She Was A Virgin? free porn video
TOTAL FANTASY – But wish I knew who she was when this picture was posted 9-years ago. It took 2 years before it received its first comment, how sad when it is such a stunning woman and pose. The original person posting the image has long since retired.
My cock pressed between her slick labia, I could feel the heat of her arousal and the fact that I had brought her to strong orgasm just moments ago had her sopping wet and creamy as I felt her opening as I pressed in. I watched her tightly closed eyes as I began penetrating her and suddenly she opened them and locked hers on mine. I felt her legs relax further and spread apart leaving me total access to her hot wet pussy as I pressed the tip inside of her.
As I continued my slow slide into her I felt my progress impeded, I stopped, I knew this feeling. The first time I had sex while still a teen I had felt the same thing and it turned out the girl was a virgin and at that time we both lost our virginity in her parents basement recreation room. Diane, the woman I had met on-line, lay below me, legs spread apart in a totally submissive position and sensed my hesitation. She moved her hands to my hips and clawed at my sides trying to pull me into her past her unbroken hymen.
“How is it possible,” I asked myself, “Diane is 25 years old and still a virgin.” The look on her face was of desperation and determination, “Do it Larry,” she said in a stern voice, “take my virginity, I want this to happen,” and then I felt her raise her hips and press against my tip.
“I had no idea,” I said, “are you sure?”
“Yes, do it, all at once, I want to feel you deep inside of me,” she said, “I am on the pill, take my virginity and cum inside of me, don’t stop.”
As I mentioned, we met online, I was rebounding from a divorce after a 25 year marriage and at the age of 50 I really had no clue how to start dating again. Nearly every site offered dating but most ended up dead ends. But when I contacted Diane we hit it off immediately and she sent me a single picture that locked the deal in my mind. I am no creep so told her exactly how old I was and she said she really wanted a mature man that knew how to treat a woman.
One meeting led to this date and she blew me off my feet when she asked if we could go back to my place. As we entered my small apartment she looked around and said, “nice and tidy, not a college dorm room with jock straps and dirty socks everywhere,” and grinned. She turned to me and without hesitation we kissed, and not a polite little hello type kiss. I parted my lips and found her tongue waiting for me.
I felt my cock stir and was hard before we finished the first kiss. It had been a couple years of me and my hand so I was so ready for a woman in my bed. Now as I looked down at her having realized she was still a virgin, I wanted to continue but felt it was a pretty important step in her life. Her eyes pleaded with me and I thrust into her as I saw her wince, blink twice, and then she humped against me and I knew whatever discomfort she felt was momentary.
I bent and sucked her nipple, it hardened in my mouth and she moaned as I started getting into a rhythm thrusting into her. I felt her hands move from my hips to the sides of my face and she pulled me and we kissed and I fucked her mouth with my tongue. When we broke the kiss she said, “I can taste me on your tongue, I hope you didn’t mind the taste,” and she grinned.
I felt her legs surround my hips pulling me deep inside and then she rocked her hips side to side holding me deep inside. I could feel her hard clit against the base of my cock and as she continued rocking back and forth I humped against her unable to get a full thrust. Then she stopped, closed her eyes, and I watched the expression on her face change and knew she was having an orgasm. I ground against her as I felt her pussy girp my cock. Then as if a switch had been flipped I felt my prostate take over and I sent a blast of hot creamy cum deep inside of her.
She opened her eyes and whispered, “I can feel you, oh I have wondered how it would feel when a man would cum inside of me.” My cock throbbed with each contraction of my prostate as my cum filled her and I felt the extra warmth of my fluids mixing with hers around my cock. When my moment passed I held my still erect cock inside of her and felt her flex her pelvic muscles against the first cock to ever make her cum.
“I feel that,” I said, “try as you might I won’t stay hard very long.”
“Then don’t waste time, fuck me again until you can’t,” she said and released her legs giving me all the room I needed. It was like I was in a frenzy as I plowed my cock into her. Being 50 years old meant my staying power and quick recovery were not that great, but she had me so aroused that I began long deep thrusts and the only sound, other than her moans, was my thighs hitting her as I bottomed out on each thrust.
Diane’s eyes were just slits in her head as she seemed carried away with the friction of my cock in her pussy. I had no illusion of cumming again but wanted her to have another orgasm. Her tits flopped in response to my pounding and her nipples were hard as rocks. I felt her meet each thrust by raising her hips meeting me half way. Just like her previous orgasm, there was no doubt when it hit her. She stopped moving, closed her eyes, and this time cried out, “ohhhh fucckkk,” and I felt her pussy tighten around my cock as her body began to convulse in another very strong orgasm.
She pulled me down onto her holding me tightly against her tits and I could hear her breath as she eased down from her orgasm, the second one from my cock inside of her previously virgin pussy. “Did you cum?” She asked between breaths.
“No, but that is okay, I am surprised I stayed hard until you got there, and that makes me happy,” I said as I slowly pulled out of her with my cock softening from my extended time in her pussy.
“I wanted you to cum in me again,” Diane said. “Maybe later,” she said and kissed me as I rolled to face her.
“I’d love to,” I said, “but you need to remember I am not one of those young college guys that have more stamina than I do.”
Diane rolled over facing me, “So you didn’t know I was still a virgin?” she asked.
“Honestly no,” I replied, “How is that even possible in today’s world?”
“I wanted to concentrate on college, every guy I was with seemed obsessed with oral and pushed for anal, which I would NEVER do. So if they enjoyed a blow job I didn’t worry about intercourse because the last thing I wanted was to just be another conquest in their college career.”
Diane fell silent for a moment with a insecure look on her face, “I understand,” I said, “I hope that my efforts were worthy of the honor of being your first.”
She replied with a deep passionate kiss and then said, “I need to use the bathroom, hope I can make it because I think you filled me full of your cum,” she said as she scooted off the bed.
I rolled onto my back and stared at the ceiling, counting the popcorn bumps on the cheap sprayed on sheetrock ceiling. The evening seemed like a dream, a wonderful fairy tale dream. When we entered the apartment our mutual passion had burst like a balloon filled beyond its capacity. After that first passionate kiss Diane pulled at my shirt baring my chest and rubbing her hands across my bare torso.
I went for her top, pulling it over her head and freed her tits from the push-up bra she was wearing. Just like the picture she had sent, whatever sag she had wasn’t worth talking about. I cupped her tits, feeling their weight and they were so firm, yet soft and her skin was smooth as silk. She moaned as I twisted her nipples.
I felt her hand move down my back and then around the front and she felt my erection, rubbing its length. She looked into my eyes, “I think you are horny,” she quipped. I replied with my hand up her skirt. Her panties were soaked and so thin it was like she was wearing nothing at all. I slipped a finger under the elastic around the leg opening and felt her hot slick slit, just as tight as in the picture. She was bald and so smooth, I knew immediately she had shaved in anticipation of us having sex.
She was breathing hard, clutching at my belt, she wanted my cock out of my pants and I was not going to refuse her. I slipped my finger between her labia and she moaned, “Oh Larry, I want to be naked, but if you keep fingering me I may just cum on your hand.”
I slid my finger up along her slit and found her clit and brushed around it and she gasped with pleasure and pulled away. She stripped out of her skirt and pulled her panties off as I kicked off my clothes as well. I stepped up to her naked body and my cock pressed between her legs, ready for the sex we both wanted. But I wanted to make sure she was as fully aroused as I was so I backed her up to the couch and pushed her back kneeling between her legs.
Diane seemed hesitant as I moved my hands along her thighs and bent kissing along her soft smooth skin. I felt her hands on my head, I stopped and looked up, “you don’t need to if you’d rather not,” she said. “I won’t if you don’t want me to, but I love starting this way if you don’t mind.” I said as I waited for her response.
She parted her legs and moved a hand down covering her bald pussy and as she pulled her hands up she parted her labia letting me see her dark pink smoothness that glistened with her arousal. I read it as an open invitation and kissed her fingers on each side of her slit and then moved my tongue along the hot gash that held the prize I wanted to earn.
She fell back against the couch and as I looked up I saw her watching me as I moved my tongue from her opening to her clit. I avoided coming in contact with her button at first, I was afraid of making it so sensitive that she’d want me to stop. She had a subtle scent that drove me wild and my immediate impulse was to mount her and fuck her silly.
I kissed and sucked her labia and felt her respond with moans and movement of her legs when the pleasure was intense. I ran my tongue up her slit and moved my fingers to her opening and before I got one knuckle deep she pressed her legs together, “Stop Larry,” she said, “I want your cock in me, I can’t wait any longer.”
I didn’t want to disobey her request, but I felt she was so close so I pulled her labia apart exposing all her treasures and ran my tongue up and around her clit and then pressed my lips around it. I flicked my tongue across her clit, now swollen and exposed from its hiding place and she froze and groaned, I had accomplished my goal and brought her to her first orgasm with me.
“Penny for your thoughts,” Diane said as she crawled back onto the bed and lay across my chest. I had been deep in thought about how this evening had played out and had not noticed she had returned.
“I was just thinking how amazing you have been tonight,” I said with a bit of a sheepish look, “I had hoped we would have sex at some point but was not planning this.”
“I was,” she said, “I knew from our first message that you were the person I wanted to be my first. I hope you understood why I stopped you when you were giving me the best oral I have ever had, I really wanted to lose my hymen with your cock.” She said as she traced lines around my bare chest with her fingers.
“I mentioned having some guys in college that I gave blow jobs, some of them tried to pleasure me with their mouth but most of them were so anxious to cum themselves that they did a lousy job. And others ate my pussy like they eat a burger, big bites and hurry up to the next bite. Most of the time I just faked an orgasm to get past it.” Diane said shifting position and straddling my spent cock.
“I hope you won’t be disappointed,” I said as I felt her grind her pussy against my cock, “I need a couple hours to recover.”
“We’ll see about that,” Diane said, “I have been told I am a master at blow jobs….”
My cock pressed between her slick labia, I could feel the heat of her arousal and the fact that I had brought her to strong orgasm just moments ago had her sopping wet and creamy as I felt her opening as I pressed in. I watched her tightly closed eyes as I began penetrating her and suddenly she opened them and locked hers on mine. I felt her legs relax further and spread apart leaving me total access to her hot wet pussy as I pressed the tip inside of her.
As I continued my slow slide into her I felt my progress impeded, I stopped, I knew this feeling. The first time I had sex while still a teen I had felt the same thing and it turned out the girl was a virgin and at that time we both lost our virginity in her parents basement recreation room. Diane, the woman I had met on-line, lay below me, legs spread apart in a totally submissive position and sensed my hesitation. She moved her hands to my hips and clawed at my sides trying to pull me into her past her unbroken hymen.
“How is it possible,” I asked myself, “Diane is 25 years old and still a virgin.” The look on her face was of desperation and determination, “Do it Larry,” she said in a stern voice, “take my virginity, I want this to happen,” and then I felt her raise her hips and press against my tip.
“I had no idea,” I said, “are you sure?”
“Yes, do it, all at once, I want to feel you deep inside of me,” she said, “I am on the pill, take my virginity and cum inside of me, don’t stop.”
As I mentioned, we met online, I was rebounding from a divorce after a 25 year marriage and at the age of 50 I really had no clue how to start dating again. Nearly every site offered dating but most ended up dead ends. But when I contacted Diane we hit it off immediately and she sent me a single picture that locked the deal in my mind. I am no creep so told her exactly how old I was and she said she really wanted a mature man that knew how to treat a woman.
One meeting led to this date and she blew me off my feet when she asked if we could go back to my place. As we entered my small apartment she looked around and said, “nice and tidy, not a college dorm room with jock straps and dirty socks everywhere,” and grinned. She turned to me and without hesitation we kissed, and not a polite little hello type kiss. I parted my lips and found her tongue waiting for me.
I felt my cock stir and was hard before we finished the first kiss. It had been a couple years of me and my hand so I was so ready for a woman in my bed. Now as I looked down at her having realized she was still a virgin, I wanted to continue but felt it was a pretty important step in her life. Her eyes pleaded with me and I thrust into her as I saw her wince, blink twice, and then she humped against me and I knew whatever discomfort she felt was momentary.
I bent and sucked her nipple, it hardened in my mouth and she moaned as I started getting into a rhythm thrusting into her. I felt her hands move from my hips to the sides of my face and she pulled me and we kissed and I fucked her mouth with my tongue. When we broke the kiss she said, “I can taste me on your tongue, I hope you didn’t mind the taste,” and she grinned.
I felt her legs surround my hips pulling me deep inside and then she rocked her hips side to side holding me deep inside. I could feel her hard clit against the base of my cock and as she continued rocking back and forth I humped against her unable to get a full thrust. Then she stopped, closed her eyes, and I watched the expression on her face change and knew she was having an orgasm. I ground against her as I felt her pussy girp my cock. Then as if a switch had been flipped I felt my prostate take over and I sent a blast of hot creamy cum deep inside of her.
She opened her eyes and whispered, “I can feel you, oh I have wondered how it would feel when a man would cum inside of me.” My cock throbbed with each contraction of my prostate as my cum filled her and I felt the extra warmth of my fluids mixing with hers around my cock. When my moment passed I held my still erect cock inside of her and felt her flex her pelvic muscles against the first cock to ever make her cum.
“I feel that,” I said, “try as you might I won’t stay hard very long.”
“Then don’t waste time, fuck me again until you can’t,” she said and released her legs giving me all the room I needed. It was like I was in a frenzy as I plowed my cock into her. Being 50 years old meant my staying power and quick recovery were not that great, but she had me so aroused that I began long deep thrusts and the only sound, other than her moans, was my thighs hitting her as I bottomed out on each thrust.
Diane’s eyes were just slits in her head as she seemed carried away with the friction of my cock in her pussy. I had no illusion of cumming again but wanted her to have another orgasm. Her tits flopped in response to my pounding and her nipples were hard as rocks. I felt her meet each thrust by raising her hips meeting me half way. Just like her previous orgasm, there was no doubt when it hit her. She stopped moving, closed her eyes, and this time cried out, “ohhhh fucckkk,” and I felt her pussy tighten around my cock as her body began to convulse in another very strong orgasm.
She pulled me down onto her holding me tightly against her tits and I could hear her breath as she eased down from her orgasm, the second one from my cock inside of her previously virgin pussy. “Did you cum?” She asked between breaths.
“No, but that is okay, I am surprised I stayed hard until you got there, and that makes me happy,” I said as I slowly pulled out of her with my cock softening from my extended time in her pussy.
“I wanted you to cum in me again,” Diane said. “Maybe later,” she said and kissed me as I rolled to face her.
“I’d love to,” I said, “but you need to remember I am not one of those young college guys that have more stamina than I do.”
Diane rolled over facing me, “So you didn’t know I was still a virgin?” she asked.
“Honestly no,” I replied, “How is that even possible in today’s world?”
“I wanted to concentrate on college, every guy I was with seemed obsessed with oral and pushed for anal, which I would NEVER do. So if they enjoyed a blow job I didn’t worry about intercourse because the last thing I wanted was to just be another conquest in their college career.”
Diane fell silent for a moment with a insecure look on her face, “I understand,” I said, “I hope that my efforts were worthy of the honor of being your first.”
She replied with a deep passionate kiss and then said, “I need to use the bathroom, hope I can make it because I think you filled me full of your cum,” she said as she scooted off the bed.
I rolled onto my back and stared at the ceiling, counting the popcorn bumps on the cheap sprayed on sheetrock ceiling. The evening seemed like a dream, a wonderful fairy tale dream. When we entered the apartment our mutual passion had burst like a balloon filled beyond its capacity. After that first passionate kiss Diane pulled at my shirt baring my chest and rubbing her hands across my bare torso.
I went for her top, pulling it over her head and freed her tits from the push-up bra she was wearing. Just like the picture she had sent, whatever sag she had wasn’t worth talking about. I cupped her tits, feeling their weight and they were so firm, yet soft and her skin was smooth as silk. She moaned as I twisted her nipples.
I felt her hand move down my back and then around the front and she felt my erection, rubbing its length. She looked into my eyes, “I think you are horny,” she quipped. I replied with my hand up her skirt. Her panties were soaked and so thin it was like she was wearing nothing at all. I slipped a finger under the elastic around the leg opening and felt her hot slick slit, just as tight as in the picture. She was bald and so smooth, I knew immediately she had shaved in anticipation of us having sex.
She was breathing hard, clutching at my belt, she wanted my cock out of my pants and I was not going to refuse her. I slipped my finger between her labia and she moaned, “Oh Larry, I want to be naked, but if you keep fingering me I may just cum on your hand.”
I slid my finger up along her slit and found her clit and brushed around it and she gasped with pleasure and pulled away. She stripped out of her skirt and pulled her panties off as I kicked off my clothes as well. I stepped up to her naked body and my cock pressed between her legs, ready for the sex we both wanted. But I wanted to make sure she was as fully aroused as I was so I backed her up to the couch and pushed her back kneeling between her legs.
Diane seemed hesitant as I moved my hands along her thighs and bent kissing along her soft smooth skin. I felt her hands on my head, I stopped and looked up, “you don’t need to if you’d rather not,” she said. “I won’t if you don’t want me to, but I love starting this way if you don’t mind.” I said as I waited for her response.
She parted her legs and moved a hand down covering her bald pussy and as she pulled her hands up she parted her labia letting me see her dark pink smoothness that glistened with her arousal. I read it as an open invitation and kissed her fingers on each side of her slit and then moved my tongue along the hot gash that held the prize I wanted to earn.
She fell back against the couch and as I looked up I saw her watching me as I moved my tongue from her opening to her clit. I avoided coming in contact with her button at first, I was afraid of making it so sensitive that she’d want me to stop. She had a subtle scent that drove me wild and my immediate impulse was to mount her and fuck her silly.
I kissed and sucked her labia and felt her respond with moans and movement of her legs when the pleasure was intense. I ran my tongue up her slit and moved my fingers to her opening and before I got one knuckle deep she pressed her legs together, “Stop Larry,” she said, “I want your cock in me, I can’t wait any longer.”
I didn’t want to disobey her request, but I felt she was so close so I pulled her labia apart exposing all her treasures and ran my tongue up and around her clit and then pressed my lips around it. I flicked my tongue across her clit, now swollen and exposed from its hiding place and she froze and groaned, I had accomplished my goal and brought her to her first orgasm with me.
“Penny for your thoughts,” Diane said as she crawled back onto the bed and lay across my chest. I had been deep in thought about how this evening had played out and had not noticed she had returned.
“I was just thinking how amazing you have been tonight,” I said with a bit of a sheepish look, “I had hoped we would have sex at some point but was not planning this.”
“I was,” she said, “I knew from our first message that you were the person I wanted to be my first. I hope you understood why I stopped you when you were giving me the best oral I have ever had, I really wanted to lose my hymen with your cock.” She said as she traced lines around my bare chest with her fingers.
“I mentioned having some guys in college that I gave blow jobs, some of them tried to pleasure me with their mouth but most of them were so anxious to cum themselves that they did a lousy job. And others ate my pussy like they eat a burger, big bites and hurry up to the next bite. Most of the time I just faked an orgasm to get past it.” Diane said shifting position and straddling my spent cock.
“I hope you won’t be disappointed,” I said as I felt her grind her pussy against my cock, “I need a couple hours to recover.”
“We’ll see about that,” Diane said, “I have been told I am a master at blow jobs….”
Mila
- 27.11.2021
- 13
- 0
