Reggie and Midge in Changing Places
- 2 years ago
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What Happened The Night Todd And Reggie Met free porn video
Reggie had taken Todd back to her condo after meeting him in a bar. They had shared a great moment with Reggie giving Todd an awesome blowjob. Then Reggie shared her secret with him as things started to get even more intimate, that she was a shemale! This story is how the night went for Reggie and Todd after this revelation.
********
“That’s okay Todd. I was enjoying your attention and was becoming excited. I had two choices - either tell you about me or stop you and push you out the door. I really like you, so I chose to share my secret with you. I hope I made the right choice here, but if you want to leave I understand,” she told him.
Todd sat there for a bit not saying much. Reggie curled herself up, leaning against the back of the couch just waiting for Todd to decide for himself what he wanted to do.
“Reggie, can I ask you some questions? I don’t mean to pry, but I was enjoying my time with you as well,” Todd said to her.
“Yes you can and I will answer honestly.”
“When did you know you were different from others?”
“When I was about thirteen, I had some medical problems. My mom took me to the doctor and of course I had tests run that showed some abnormalities. The family doctor wasn’t sure what he was seeing so he sent my mom to see a specialist for me.”
“So this was when you found out you were different from other boys?”
“This was the beginning and then as I got a little older and things were changing even more…"
Reggie went on to explain how she became the person who she was sitting there with Todd at this moment.
"So Todd, now you know more than almost anybody about how I became Reggie and not Reginal.”
They both sat there for a bit after Reggie finished her story, Todd in thought and Reggie in nervous contemplation over sharing her story with Todd. Finally Todd reached out to her; she reached her hand out to him. Encouraged by this action she slid closer to him as he pulled her hand to his lips. He gave her hand a light kiss.
Ever so slowly they moved closer until they were making out as they had been in the bar. Todd slid his hand inside her robe caressing her breasts as their tongues danced together. She moved her hand down to his cock stroking him to hardness again. Both of them were moaning at the touches of each other.
Reggie could feel herself becoming hard as Todd caressed her breasts and felt now was the time to see his reaction to touching her. She released his cock and caught his free hand in hers. She guided it to her hardening cock. He tensed slightly as she placed his hand on her cock, but slowly relaxed and started stroking her gently. She went back to stroking his cock as they continued passionately kissing.
Reggie broke their kiss and leaned back to slide off her robe. Todd also took this opportunity to strip the rest of his clothes off since she had only taken his pants and underwear off earlier. Now both naked and exposed to each other they started to explore. Todd still a little hesitant at first with her, but soon he had overcome all his discomfort and begin to fondle Reggie’s cock, stroking it and rubbing it as she was doing to his.
Todd leaned forward and caught a nipple in his mouth, sucking it sharply between his teeth causing a loud gasp moan to escape from Reggie. He was alternating between her nipples as he was stroking her cock with one hand and massaging her breasts with the other. Reggie was beside herself with the stimulation he was providing.
Leaning towards Todd’s ear she whispered, "Would you please take me?’
For his part Todd never hesitated, but instead just replied, “Yes!”
Getting up she said, “I’ll be right back.”
Reggie returned with a package of condoms and a bottle of lube for them to use. Kneeling in front of Todd she pulled one of the condoms from its packet. Grasping his cock in her hand she took him in her mouth until he felt his cock slide into her tight throat. She then pulled him back out leaving a trail of saliva and pre-cum mixed on his cock. She slowly rolled the condom down his cock until she had him completely covered to the base.
Looking up at him she asked, “Do you want to take me from behind or be facing me?”
Todd never having experienced even anal with a normal woman was at a loss for an answer to her question. He finally blurted out whatever feels the best to you.
Realizing she would need to take the lead for now, she grabbed his hand pulling him off the couch to the floor beside her. She also grabbed a big pillow that was resting on the couch near them. Reggie laid the pillow down on the floor and maneuvered herself on it so it was at the base of her back and the top of her buttocks. She wiggled a bit too comfortable before looking up at Todd.
“Come here and let me lube you up a bit.” Taking the bottle lube she applied a generous amount into her hand and started stroking his cock stretching the condom over it even tighter while applying the lube.
“Here Todd, you take this and finger my asshole with a lot of lube. I’ll be tight for you at first, but will relax quickly,” she explained to him.
Todd having no experience squirted a little lube on his fingers and gently placed them at her puckered opening. He slowly pushed his fingers against her opening, ever so slowly breaking past the resistance of her muscles. He worked them in and out causing an involuntary moan to escape from Reggie.
Looking up at him, she said, “Please enter me... I want you so bad right now!”
Not needing to be asked twice, Todd positioned himself to enter her asshole. He placed the tip of his cock against her opening and pushed gently feeling it give a bit. Realizing it was going to take more pressure to enter her he leaned forward a bit and pushed harder. With a bit of surprise to both of them his cock head popped through quickly causing a surprised intake of breath from him and a low moan of excitement form her.
Reggie told him to take it nice and slow until they both got comfortable. He followed her instructions and slowly pushed deeper until he was all the way in. He could feel his balls lying against her ass as he was so close to her. Ever so slowly he pulled back a bit and slid forward. The feeling was like nothing he had ever experienced with a woman before. He could feel Reggie loosening up as he continued his easy back and forth motion until he was pulling mostly out and ramming back into her hard and fast.
Reggie was moaning in pleasure and excitement at his actions, yelling encouragement for him to fill her full of his cock. She was withering under him as he pounded her, being scooted on the floor from his actions.
Todd was looking at Reggie as he fucked her in the ass thinking, “How wonderful she felt to him this way.” Never having done anal before he had no idea what the sensations would be and now that he did, he was loving it.
He saw her cock bouncing around semi-hard as he continued to pound into her and without much consideration for what he was doing, he grasped it in his hand and started stroking it. This action caused Reggie to let out a gasp and even a louder and longer moan than she had been doing. He continued to stroke her cock all the while working his own in and out of her ass, but he knew the end was near for him, he could feel his impending orgasm. He redoubled his efforts on her cock, wanting her to cum along with, never knowing if she even could.
“I’m going to cum!” shouted Todd, pushing deep into Reggie as he could while still quickly stroking her cock as well. He felt his cock swell as he emptied himself into the condom buried deep in her ass. Suddenly he felt her asshole tighten around and without any warning Reggie started cumming as well, sending long jets of spunk flying, to land on her stomach and breasts.
“Oh my God! It’s been so long since I had a man make me cum during sex. That felt so good, thank you for that,” Reggie weakly told him.
Todd just collapsed on her afterwards. His cock still buried in her asshole, slowly softening. She finally told him to pull out, but be very gentle as not lose the condom while pulling out.
Once he had fully pulled out of her, Reggie got up and went back to the bathroom. She came back carrying a paper towel, a washcloth and a hand towel. Sitting down beside Todd she gently removed his condom and wrapped it in the paper towel, tossing it in a nearby waste basket. She then slowly washed his cock and balls of the mess that had been made during their sex. Afterwards she dried him off, but couldn’t help but stroke him a few times. She then cleaned the cum off her stomach and chest with the washcloth, but knowing she would need a shower for the rest.
Todd leaned towards her and gave her a kiss on the cheek that quickly developed into a passionate kiss when Reggie turned her head towards him. They stayed this way, sharing their intimate moment a bit longer until they both needed to get air.
“Would you like to stay the night with me?” asked Reggie.
Todd not needing to think, nodded his head yes. She stood up holding her hand out to him to take. He got up and they we started back towards her bedroom.
Morning found them in Reggie’s bed together, curled up like the lovers they had become.
********
“That’s okay Todd. I was enjoying your attention and was becoming excited. I had two choices - either tell you about me or stop you and push you out the door. I really like you, so I chose to share my secret with you. I hope I made the right choice here, but if you want to leave I understand,” she told him.
Todd sat there for a bit not saying much. Reggie curled herself up, leaning against the back of the couch just waiting for Todd to decide for himself what he wanted to do.
“Reggie, can I ask you some questions? I don’t mean to pry, but I was enjoying my time with you as well,” Todd said to her.
“Yes you can and I will answer honestly.”
“When did you know you were different from others?”
“When I was about thirteen, I had some medical problems. My mom took me to the doctor and of course I had tests run that showed some abnormalities. The family doctor wasn’t sure what he was seeing so he sent my mom to see a specialist for me.”
“So this was when you found out you were different from other boys?”
“This was the beginning and then as I got a little older and things were changing even more…"
Reggie went on to explain how she became the person who she was sitting there with Todd at this moment.
"So Todd, now you know more than almost anybody about how I became Reggie and not Reginal.”
They both sat there for a bit after Reggie finished her story, Todd in thought and Reggie in nervous contemplation over sharing her story with Todd. Finally Todd reached out to her; she reached her hand out to him. Encouraged by this action she slid closer to him as he pulled her hand to his lips. He gave her hand a light kiss.
Ever so slowly they moved closer until they were making out as they had been in the bar. Todd slid his hand inside her robe caressing her breasts as their tongues danced together. She moved her hand down to his cock stroking him to hardness again. Both of them were moaning at the touches of each other.
Reggie could feel herself becoming hard as Todd caressed her breasts and felt now was the time to see his reaction to touching her. She released his cock and caught his free hand in hers. She guided it to her hardening cock. He tensed slightly as she placed his hand on her cock, but slowly relaxed and started stroking her gently. She went back to stroking his cock as they continued passionately kissing.
Reggie broke their kiss and leaned back to slide off her robe. Todd also took this opportunity to strip the rest of his clothes off since she had only taken his pants and underwear off earlier. Now both naked and exposed to each other they started to explore. Todd still a little hesitant at first with her, but soon he had overcome all his discomfort and begin to fondle Reggie’s cock, stroking it and rubbing it as she was doing to his.
Todd leaned forward and caught a nipple in his mouth, sucking it sharply between his teeth causing a loud gasp moan to escape from Reggie. He was alternating between her nipples as he was stroking her cock with one hand and massaging her breasts with the other. Reggie was beside herself with the stimulation he was providing.
Leaning towards Todd’s ear she whispered, "Would you please take me?’
For his part Todd never hesitated, but instead just replied, “Yes!”
Getting up she said, “I’ll be right back.”
Reggie returned with a package of condoms and a bottle of lube for them to use. Kneeling in front of Todd she pulled one of the condoms from its packet. Grasping his cock in her hand she took him in her mouth until he felt his cock slide into her tight throat. She then pulled him back out leaving a trail of saliva and pre-cum mixed on his cock. She slowly rolled the condom down his cock until she had him completely covered to the base.
Looking up at him she asked, “Do you want to take me from behind or be facing me?”
Todd never having experienced even anal with a normal woman was at a loss for an answer to her question. He finally blurted out whatever feels the best to you.
Realizing she would need to take the lead for now, she grabbed his hand pulling him off the couch to the floor beside her. She also grabbed a big pillow that was resting on the couch near them. Reggie laid the pillow down on the floor and maneuvered herself on it so it was at the base of her back and the top of her buttocks. She wiggled a bit too comfortable before looking up at Todd.
“Come here and let me lube you up a bit.” Taking the bottle lube she applied a generous amount into her hand and started stroking his cock stretching the condom over it even tighter while applying the lube.
“Here Todd, you take this and finger my asshole with a lot of lube. I’ll be tight for you at first, but will relax quickly,” she explained to him.
Todd having no experience squirted a little lube on his fingers and gently placed them at her puckered opening. He slowly pushed his fingers against her opening, ever so slowly breaking past the resistance of her muscles. He worked them in and out causing an involuntary moan to escape from Reggie.
Looking up at him, she said, “Please enter me... I want you so bad right now!”
Not needing to be asked twice, Todd positioned himself to enter her asshole. He placed the tip of his cock against her opening and pushed gently feeling it give a bit. Realizing it was going to take more pressure to enter her he leaned forward a bit and pushed harder. With a bit of surprise to both of them his cock head popped through quickly causing a surprised intake of breath from him and a low moan of excitement form her.
Reggie told him to take it nice and slow until they both got comfortable. He followed her instructions and slowly pushed deeper until he was all the way in. He could feel his balls lying against her ass as he was so close to her. Ever so slowly he pulled back a bit and slid forward. The feeling was like nothing he had ever experienced with a woman before. He could feel Reggie loosening up as he continued his easy back and forth motion until he was pulling mostly out and ramming back into her hard and fast.
Reggie was moaning in pleasure and excitement at his actions, yelling encouragement for him to fill her full of his cock. She was withering under him as he pounded her, being scooted on the floor from his actions.
Todd was looking at Reggie as he fucked her in the ass thinking, “How wonderful she felt to him this way.” Never having done anal before he had no idea what the sensations would be and now that he did, he was loving it.
He saw her cock bouncing around semi-hard as he continued to pound into her and without much consideration for what he was doing, he grasped it in his hand and started stroking it. This action caused Reggie to let out a gasp and even a louder and longer moan than she had been doing. He continued to stroke her cock all the while working his own in and out of her ass, but he knew the end was near for him, he could feel his impending orgasm. He redoubled his efforts on her cock, wanting her to cum along with, never knowing if she even could.
“I’m going to cum!” shouted Todd, pushing deep into Reggie as he could while still quickly stroking her cock as well. He felt his cock swell as he emptied himself into the condom buried deep in her ass. Suddenly he felt her asshole tighten around and without any warning Reggie started cumming as well, sending long jets of spunk flying, to land on her stomach and breasts.
“Oh my God! It’s been so long since I had a man make me cum during sex. That felt so good, thank you for that,” Reggie weakly told him.
Todd just collapsed on her afterwards. His cock still buried in her asshole, slowly softening. She finally told him to pull out, but be very gentle as not lose the condom while pulling out.
Once he had fully pulled out of her, Reggie got up and went back to the bathroom. She came back carrying a paper towel, a washcloth and a hand towel. Sitting down beside Todd she gently removed his condom and wrapped it in the paper towel, tossing it in a nearby waste basket. She then slowly washed his cock and balls of the mess that had been made during their sex. Afterwards she dried him off, but couldn’t help but stroke him a few times. She then cleaned the cum off her stomach and chest with the washcloth, but knowing she would need a shower for the rest.
Todd leaned towards her and gave her a kiss on the cheek that quickly developed into a passionate kiss when Reggie turned her head towards him. They stayed this way, sharing their intimate moment a bit longer until they both needed to get air.
“Would you like to stay the night with me?” asked Reggie.
Todd not needing to think, nodded his head yes. She stood up holding her hand out to him to take. He got up and they we started back towards her bedroom.
Morning found them in Reggie’s bed together, curled up like the lovers they had become.
Lizbeth
- 30.09.2021
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