Wartime Comfort House Diary Day 8 Shemale
- 2 years ago
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First Time Fucked By A Shemale free porn video
I repair computers, often "on site"--in people's homes. I got a call from a woman asking me to come to her house to fix her PC. She told me her name was Shandra. We made arrangements for me to show up there Saturday afternoon.
I showed up at the appointed time and was surprised when I saw her--she was taller than I am (I'm 5'11", she had to be at least 6'2") and fairly stocky. She looked like she could kick my ass in a wrestling match, but had an unmistakable femininity.
Her hair was dirty blond and loosely curled, and her face was quite beautiful. She was wearing makeup, but it was understated and complimented her face rather than drawing attention to the makeup itself. She was wearing a white sort of half-T-shirt that came halfway down to her belly button, exposing a flat, toned belly, but covering her boobs which stuck out way past her belly and threatened to bust out of her tight t-shirt. The only other item of clothing she was wearing were faded blue jeans which were cut off and made into shorts. They were covering an enormous, but perfectly-shaped ass and the tops of her large, powerful-looking legs. I also noticed that she had broad shoulders and slightly larger, well-muscled arms for a woman, but not so large or muscular that they looked unattractive.
When she greeted me, she gave me a quick look up and down, then smiled and told me to come in.
"Would you like something to drink?" she asked. I said "sure, what do you have?" She offered me beer or a frozen margarita. "Well, I'd like to keep my head clear for the work. Maybe later." "Well then, how about some Orange Juice?" she asked, and I agreed.
I said I'd like to get started and asked her where the PC was. She told me it was the second door on the right down the hall, I went in there and it turned out to be the bedroom. I couldn't help but notice a huge jar of Vaseline on her bedside table, along with tubes of K-Y jelly and Astroglide. The bedsheets were red satin, and there were no blankets or bedspread. By then I started to wonder if Shandra had more on her mind than getting her PC fixed.
I got started on the computer and a little while later she came in with the OJ. "Can you tell why it won't start up?" she asked as she handed me the juice. "I think so, and it shouldn't take too long to fix," I said. "Well, that's the best news I've had all day!" Shandra said, and gave me an odd smile that was almost a leer.
A short while later I had fixed the PC, much to her delight. When it booted, the desktop wallpaper was a photo of Shandra--naked. Her breasts were all I'd imagined... then I noticed she had a cock and balls!! Her cock was erect in the photo and looked about six or seven inches and about average thickness. My mouth dropped open as I stared at the photo. Shandra saw me looking at it, walked over to me, put her hand on my shoulder and said "Well, how do you like it?" I said "You look gorgeous. You have a great ass and huge, natural-looking tits!" She said, "And what do you think of my dick?" I was so excited I was actually shaking. I like to look at shemale porn, but had never seen a real, live shemale! "You have a nice big dick, it looks good," I said. Shandra grinned, and looked at me like a hungry tiger looks at fresh meat. She said, "Well you've seen me naked, now it's only fair that I see you naked too."
I was really trembling by that point, and wanted to leave, so I could get this all sorted out. It was all happening too fast for me. I said "Uh, I guess I should be going now." Shandra looked into my eyes and said "Oh, you can't go yet. I'm not done with you!"
That both thrilled me and scared me a little, and I didn't know what to say. I had fantasized about being with a shemale many times, but never thought about actually doing it. All my past sexual experiences had been with women. I wasn't prepared for this, and part of me wanted to leave, but another part was very curious about what might happen.
She moved closer to me, took my hands and put them on her breasts. I started fondling them and could feel the nipples start to harden beneath the t-shirt and bra. She started pulling my shirt off. "Wait," I said, "I'm not sure I want to do this." Shandra replied "You can't expect to leave after seeing me naked and feeling me up. You've got me horny now and you have to do something about it. I can tell you've never been with a shemale before. I'm glad to have the privilege of taking your virginity. Don't worry, I'll be gentle!" She laughed evilly. I tried to back away but she had a hold of my shirt and pulled it off, then she wrapped her strong arms around me and started kissing me, forcing her tongue past my lips. I was getting hornier but still a little scared, and I was trembling and my arm and leg muscles felt funny and weak. I couldn't fight her off, and wasn't sure I wanted to at that point.
Her hands moved down and started squeezing my ass cheeks. "I can't wait to get in there!" she said. At the time, I had no idea what she meant!
She quickly took off her shirt and bra and then took my head into her hands and slowly but forcefully pushed my face into her chest, and swung her torso back and forth, gently battering my face with her tits. By this time, I was hard as a rock! She then released my head and started unzipping my pants. I half-heartedly tried to push her hands away, but she batted mine away and said "Stop resisting. You have to let me see you naked, you're not getting out of here until you do. Just relax, all I want to do is see that luscious ass of yours and then I'll let you go." Well, that was quite a relief, and I was very flattered, never having my ass referred to as "luscious" before.
I said, "Well, I guess that's fair." I let her take off my pants and underwear. As I stood there naked, facing her, with her huge breasts sticking out from her chest; I looked down and noticed a very large bulge in her shorts. I felt flattered that Shandra was so turned on by me, but worried about the thing that was trying to bust out of her shorts! She looked me up and down and said, "Nice cock. Now turn around!" I did as I was told. Shandra said, "God, what a great ass you have," then she grabbed my butt cheeks and started gently squeezing them, then squeezed harder and harder until it actually started to hurt just a little. I was about to say something, but she spoke first. "Lay down on the bed," she said. At that point I was incredibly horny and all the doubts about what I was doing were gone. I was really hoping for a blowjob! So I lay down on the bed on my back, and she said "No, turn over." I wondered what she wanted me to turn over for, and she saw the concern in my face and said "Don't worry babe, I just want to fondle and massage that ass of yours some more."
I said OK and turned over. She got up on the bed, standing over me for a minute, and then straddled my legs so she was facing my butt. She started rubbing and massaging my ass again, and I was getting so horny I was about to explode! She stopped what she was doing, said "you just stay there a minute, and don't look back--I have a surprise for you" and stood up. I again did as I was told, and she was walking around on the bed for a minute. Just as I started to wonder what she was doing, she sat back down just like before and immediately started massaging and gently slapping my ass. It was nice, but something seemed different. She then leaned over me to the bedside table, reached into the Vaseline jar and pulled out a good-sized glob of it. I figured she was going to give me a Vaseline massage, and I could hear her working the lube into her hands, or so I thought. Suddenly, I felt something large, warm and slippery rubbing my ass! I looked back to see what was happening, and gasped as I saw that she had taken off her shorts, lubed up her crank and was rubbing my ass with it!! Damn, it looked a lot bigger from that angle than it had in the photo! "Just relax, honey buns, I can tell this is your first time at this and I promise I'll be gentle." she said. My boner wilted quickly as I realized what she was planning to do, and I nearly panicked! I said "Wait, I don't want this! Get off me! You can't do this!!"
She replied angrily, "I'm not letting you get away with that prick-teasing shit! You march your cute ass in here, parade it around in front of me, let me get my hands on it and then after you've gotten me all horny, you think you can say no?" Then she continued in a much gentler tone, "Just relax, sweetheart. I'm going to take care of you. I know how to please a man... you just have to let me fuck you first and then I'll get you off afterwards." My world reeled--how is this possible? An hour ago I was on my way to a computer repair job, now a shemale is trying to **** me?
I started to try to get up but she leaned over me and held me down. In that position, I couldn't do anything, and I could feel her throbbing log resting on my butt crack. She said "Don't fight it babe, if you fight it, it'll hurt." I couldn't believe my ears... I was about to get ****d by a she-male, and she was worried that she might hurt me??
The next thing I knew, she had positioned her dick so the tip of it was pressing gently on my butt hole. I felt my sphincter tighten up involuntarily and was afraid she'd thrust in then... my whole body was shaking with fear. But she just held it there, until my asshole relaxed, then she pushed against it just a tiny bit, at which point it went taught again, and again she stopped and held it there. My bunghole relaxed again, and she pushed it into my ass just a little. My butt clenched again and this time it hurt a little, because it couldn't close all the way as the tip of her erect penis was in there! She held it rock-steady, though, and this time my anus let loose even sooner than before. Slowly, slowly, she began to slide the rest of her log into me. I didn't clench again, but it was horribly uncomfortable--it felt like it just kept going in and in forever, filling me up beyond all possibility.
"Ahhhh," she said, "That's nice. That feels so good..." She was still sitting on my legs, and then she straightened out her legs behind her and lay down on me, which cause her penis to slide in even further! She just lay on me for a while, not moving, and said, "GOD it feels SO GOOD to be inside you! You're going to be the best fuck ever, your pussy is so hot and tight!!" When I heard that I felt a strange rush of exhilaration. I could feel her boobs pressing into my back and feel her breath on the back of my neck. I felt myself starting to get hard again! I couldn't believe it, I was getting ass-****d and this was making my dick hard?
Still laying on me, she arched her back to pull her cock out slightly, then thrust it back in slowly. She kept doing this, and it was starting to feel good to me! I was getting butt-fucked by a shemale, and I was liking it! Hell, I was starting to love it! She started to moan, and began to pump my butt a little faster. She kept this up for a while, telling me how good it felt. My cock was so hard it was actually starting to ache a bit! I couldn't help but let out a moan or two… then she pushed herself partially off me, straightening her arms, and started fucking me like some crazed a****l! Her thrusting into my ass was moving my whole body on the bed, and my cock was sliding around on the satin sheet. It felt so good... then I realized I was going to have an orgasm!
I tried to hold back, but I couldn't. I started to come, and it was the most intense, mind-shattering orgasm of my life! With each orgasmic contraction, I could feel my butthole tighten convulsively on her log, and as soon as my orgasm started, she began moaning and grunting louder, then with one powerful thrust, shoved her fuck stick deep into me and held it there. As I was coming and feeling my asshole tighten and release, tighten and release on her cock with each wave of orgasm, I could also feel her cock pulsating inside me as she came too! I swear I felt her jizz squirting deep into me, and with each of her orgasmic pulses her whole body contracted powerfully as she cried out, which made my orgasm suddenly double in intensity! It seemed to go on forever--I think I came at least twice in rapid succession, and it felt like my head and my heart were going to explode!
As we finished coming, she collapsed on top of me, with her cock still inside. After that incredibly powerful orgasm, I was more relaxed than I've ever been before or since.
We lay there like that, breathing hard, and I felt her penis slowly soften and shrink, but it stayed in my butt. We stayed like that for a while, and I think one or both of us may have dozed a bit. I'd just been fucked, practically ****d, had my ass used by a gorgeous "woman" for her selfish pleasure. It was the most beautiful feeling I had ever felt!! I could have lay there forever with her on top of me and her cock in my ass and her boobs mashed onto my back. I wanted to do it again, and often. I wanted to be Shandra's sex doll.
Suddenly she suddenly said, "Oh shit, what time is it? I have to get to my yoga class!" She pulled out of me and went into the bathroom. When she came out she was dressed again, and said to me, "Bathroom's in there, sweetie. Get cleaned up and dressed quickly, ok? I don't want to be late. How much do I owe you?"
I was puzzled. She said, "For the computer repair, silly!" I had completely forgotten about that! I was still reeling with bliss from the experience, and all I could say was "Uh..." She smiled and said "Don't worry about it now; you can give me the bill when you come next week." I said, "Huh? Next week?"
Shandra replied, "You fixed the PC, but I'm sure I'll need you to come back every weekend for tune-ups and stuff, so it doesn't crash again." She gave me an evil grin, and added "And don't forget, you're my bitch now. You're my fuck-toy and I'm going to take good care of you. Now get dressed and get the hell out of here so I can go to the yoga class!"
I showed up at the appointed time and was surprised when I saw her--she was taller than I am (I'm 5'11", she had to be at least 6'2") and fairly stocky. She looked like she could kick my ass in a wrestling match, but had an unmistakable femininity.
Her hair was dirty blond and loosely curled, and her face was quite beautiful. She was wearing makeup, but it was understated and complimented her face rather than drawing attention to the makeup itself. She was wearing a white sort of half-T-shirt that came halfway down to her belly button, exposing a flat, toned belly, but covering her boobs which stuck out way past her belly and threatened to bust out of her tight t-shirt. The only other item of clothing she was wearing were faded blue jeans which were cut off and made into shorts. They were covering an enormous, but perfectly-shaped ass and the tops of her large, powerful-looking legs. I also noticed that she had broad shoulders and slightly larger, well-muscled arms for a woman, but not so large or muscular that they looked unattractive.
When she greeted me, she gave me a quick look up and down, then smiled and told me to come in.
"Would you like something to drink?" she asked. I said "sure, what do you have?" She offered me beer or a frozen margarita. "Well, I'd like to keep my head clear for the work. Maybe later." "Well then, how about some Orange Juice?" she asked, and I agreed.
I said I'd like to get started and asked her where the PC was. She told me it was the second door on the right down the hall, I went in there and it turned out to be the bedroom. I couldn't help but notice a huge jar of Vaseline on her bedside table, along with tubes of K-Y jelly and Astroglide. The bedsheets were red satin, and there were no blankets or bedspread. By then I started to wonder if Shandra had more on her mind than getting her PC fixed.
I got started on the computer and a little while later she came in with the OJ. "Can you tell why it won't start up?" she asked as she handed me the juice. "I think so, and it shouldn't take too long to fix," I said. "Well, that's the best news I've had all day!" Shandra said, and gave me an odd smile that was almost a leer.
A short while later I had fixed the PC, much to her delight. When it booted, the desktop wallpaper was a photo of Shandra--naked. Her breasts were all I'd imagined... then I noticed she had a cock and balls!! Her cock was erect in the photo and looked about six or seven inches and about average thickness. My mouth dropped open as I stared at the photo. Shandra saw me looking at it, walked over to me, put her hand on my shoulder and said "Well, how do you like it?" I said "You look gorgeous. You have a great ass and huge, natural-looking tits!" She said, "And what do you think of my dick?" I was so excited I was actually shaking. I like to look at shemale porn, but had never seen a real, live shemale! "You have a nice big dick, it looks good," I said. Shandra grinned, and looked at me like a hungry tiger looks at fresh meat. She said, "Well you've seen me naked, now it's only fair that I see you naked too."
I was really trembling by that point, and wanted to leave, so I could get this all sorted out. It was all happening too fast for me. I said "Uh, I guess I should be going now." Shandra looked into my eyes and said "Oh, you can't go yet. I'm not done with you!"
That both thrilled me and scared me a little, and I didn't know what to say. I had fantasized about being with a shemale many times, but never thought about actually doing it. All my past sexual experiences had been with women. I wasn't prepared for this, and part of me wanted to leave, but another part was very curious about what might happen.
She moved closer to me, took my hands and put them on her breasts. I started fondling them and could feel the nipples start to harden beneath the t-shirt and bra. She started pulling my shirt off. "Wait," I said, "I'm not sure I want to do this." Shandra replied "You can't expect to leave after seeing me naked and feeling me up. You've got me horny now and you have to do something about it. I can tell you've never been with a shemale before. I'm glad to have the privilege of taking your virginity. Don't worry, I'll be gentle!" She laughed evilly. I tried to back away but she had a hold of my shirt and pulled it off, then she wrapped her strong arms around me and started kissing me, forcing her tongue past my lips. I was getting hornier but still a little scared, and I was trembling and my arm and leg muscles felt funny and weak. I couldn't fight her off, and wasn't sure I wanted to at that point.
Her hands moved down and started squeezing my ass cheeks. "I can't wait to get in there!" she said. At the time, I had no idea what she meant!
She quickly took off her shirt and bra and then took my head into her hands and slowly but forcefully pushed my face into her chest, and swung her torso back and forth, gently battering my face with her tits. By this time, I was hard as a rock! She then released my head and started unzipping my pants. I half-heartedly tried to push her hands away, but she batted mine away and said "Stop resisting. You have to let me see you naked, you're not getting out of here until you do. Just relax, all I want to do is see that luscious ass of yours and then I'll let you go." Well, that was quite a relief, and I was very flattered, never having my ass referred to as "luscious" before.
I said, "Well, I guess that's fair." I let her take off my pants and underwear. As I stood there naked, facing her, with her huge breasts sticking out from her chest; I looked down and noticed a very large bulge in her shorts. I felt flattered that Shandra was so turned on by me, but worried about the thing that was trying to bust out of her shorts! She looked me up and down and said, "Nice cock. Now turn around!" I did as I was told. Shandra said, "God, what a great ass you have," then she grabbed my butt cheeks and started gently squeezing them, then squeezed harder and harder until it actually started to hurt just a little. I was about to say something, but she spoke first. "Lay down on the bed," she said. At that point I was incredibly horny and all the doubts about what I was doing were gone. I was really hoping for a blowjob! So I lay down on the bed on my back, and she said "No, turn over." I wondered what she wanted me to turn over for, and she saw the concern in my face and said "Don't worry babe, I just want to fondle and massage that ass of yours some more."
I said OK and turned over. She got up on the bed, standing over me for a minute, and then straddled my legs so she was facing my butt. She started rubbing and massaging my ass again, and I was getting so horny I was about to explode! She stopped what she was doing, said "you just stay there a minute, and don't look back--I have a surprise for you" and stood up. I again did as I was told, and she was walking around on the bed for a minute. Just as I started to wonder what she was doing, she sat back down just like before and immediately started massaging and gently slapping my ass. It was nice, but something seemed different. She then leaned over me to the bedside table, reached into the Vaseline jar and pulled out a good-sized glob of it. I figured she was going to give me a Vaseline massage, and I could hear her working the lube into her hands, or so I thought. Suddenly, I felt something large, warm and slippery rubbing my ass! I looked back to see what was happening, and gasped as I saw that she had taken off her shorts, lubed up her crank and was rubbing my ass with it!! Damn, it looked a lot bigger from that angle than it had in the photo! "Just relax, honey buns, I can tell this is your first time at this and I promise I'll be gentle." she said. My boner wilted quickly as I realized what she was planning to do, and I nearly panicked! I said "Wait, I don't want this! Get off me! You can't do this!!"
She replied angrily, "I'm not letting you get away with that prick-teasing shit! You march your cute ass in here, parade it around in front of me, let me get my hands on it and then after you've gotten me all horny, you think you can say no?" Then she continued in a much gentler tone, "Just relax, sweetheart. I'm going to take care of you. I know how to please a man... you just have to let me fuck you first and then I'll get you off afterwards." My world reeled--how is this possible? An hour ago I was on my way to a computer repair job, now a shemale is trying to **** me?
I started to try to get up but she leaned over me and held me down. In that position, I couldn't do anything, and I could feel her throbbing log resting on my butt crack. She said "Don't fight it babe, if you fight it, it'll hurt." I couldn't believe my ears... I was about to get ****d by a she-male, and she was worried that she might hurt me??
The next thing I knew, she had positioned her dick so the tip of it was pressing gently on my butt hole. I felt my sphincter tighten up involuntarily and was afraid she'd thrust in then... my whole body was shaking with fear. But she just held it there, until my asshole relaxed, then she pushed against it just a tiny bit, at which point it went taught again, and again she stopped and held it there. My bunghole relaxed again, and she pushed it into my ass just a little. My butt clenched again and this time it hurt a little, because it couldn't close all the way as the tip of her erect penis was in there! She held it rock-steady, though, and this time my anus let loose even sooner than before. Slowly, slowly, she began to slide the rest of her log into me. I didn't clench again, but it was horribly uncomfortable--it felt like it just kept going in and in forever, filling me up beyond all possibility.
"Ahhhh," she said, "That's nice. That feels so good..." She was still sitting on my legs, and then she straightened out her legs behind her and lay down on me, which cause her penis to slide in even further! She just lay on me for a while, not moving, and said, "GOD it feels SO GOOD to be inside you! You're going to be the best fuck ever, your pussy is so hot and tight!!" When I heard that I felt a strange rush of exhilaration. I could feel her boobs pressing into my back and feel her breath on the back of my neck. I felt myself starting to get hard again! I couldn't believe it, I was getting ass-****d and this was making my dick hard?
Still laying on me, she arched her back to pull her cock out slightly, then thrust it back in slowly. She kept doing this, and it was starting to feel good to me! I was getting butt-fucked by a shemale, and I was liking it! Hell, I was starting to love it! She started to moan, and began to pump my butt a little faster. She kept this up for a while, telling me how good it felt. My cock was so hard it was actually starting to ache a bit! I couldn't help but let out a moan or two… then she pushed herself partially off me, straightening her arms, and started fucking me like some crazed a****l! Her thrusting into my ass was moving my whole body on the bed, and my cock was sliding around on the satin sheet. It felt so good... then I realized I was going to have an orgasm!
I tried to hold back, but I couldn't. I started to come, and it was the most intense, mind-shattering orgasm of my life! With each orgasmic contraction, I could feel my butthole tighten convulsively on her log, and as soon as my orgasm started, she began moaning and grunting louder, then with one powerful thrust, shoved her fuck stick deep into me and held it there. As I was coming and feeling my asshole tighten and release, tighten and release on her cock with each wave of orgasm, I could also feel her cock pulsating inside me as she came too! I swear I felt her jizz squirting deep into me, and with each of her orgasmic pulses her whole body contracted powerfully as she cried out, which made my orgasm suddenly double in intensity! It seemed to go on forever--I think I came at least twice in rapid succession, and it felt like my head and my heart were going to explode!
As we finished coming, she collapsed on top of me, with her cock still inside. After that incredibly powerful orgasm, I was more relaxed than I've ever been before or since.
We lay there like that, breathing hard, and I felt her penis slowly soften and shrink, but it stayed in my butt. We stayed like that for a while, and I think one or both of us may have dozed a bit. I'd just been fucked, practically ****d, had my ass used by a gorgeous "woman" for her selfish pleasure. It was the most beautiful feeling I had ever felt!! I could have lay there forever with her on top of me and her cock in my ass and her boobs mashed onto my back. I wanted to do it again, and often. I wanted to be Shandra's sex doll.
Suddenly she suddenly said, "Oh shit, what time is it? I have to get to my yoga class!" She pulled out of me and went into the bathroom. When she came out she was dressed again, and said to me, "Bathroom's in there, sweetie. Get cleaned up and dressed quickly, ok? I don't want to be late. How much do I owe you?"
I was puzzled. She said, "For the computer repair, silly!" I had completely forgotten about that! I was still reeling with bliss from the experience, and all I could say was "Uh..." She smiled and said "Don't worry about it now; you can give me the bill when you come next week." I said, "Huh? Next week?"
Shandra replied, "You fixed the PC, but I'm sure I'll need you to come back every weekend for tune-ups and stuff, so it doesn't crash again." She gave me an evil grin, and added "And don't forget, you're my bitch now. You're my fuck-toy and I'm going to take good care of you. Now get dressed and get the hell out of here so I can go to the yoga class!"
Latisha
- 31.05.2021
- 47
- 0
