How to Strap on Training Experience
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My First Strap On Experience With My First Crush free porn video
A little about me: I have been interested in strap-on sex for about 8 or 9 years. As a black male in his 20s, finding a woman who is interested in doing this is very difficult, as they are always quick to jump to conclusions about your sexuality.
However, my best female friend apparently had the same interest. One day in 2008, while talking on the phone, she says to me randomly "...so how would you like if I lay you on your back and fuck you with a 12" strap-on?" I was caught off guard, but I immediately was horny. Not knowing what to say, I said "wow...I don't know about that...". She proceeded to say "Come on B, I'll put it in nice and slow. I will go easy on you..." I was ready to bust a nut right then, and I didn't even touch my dick. I downplayed the scenario, wondering if she was being honest or not, and we soon forgot about it.
Fast forward to 2010. I have a long-term girlfriend, who my friend does not necessarily care for. We always talk about sex. Not with each other, but just random sex acts. While in one of our typical conversations, I decide to go all in and throw it out there and asked her "do you still think about strap-on sex?" she said "well...not really. why are you interested?" I told her that yes I was, and that actually I was immediately turned on by what she had told me a few years prior. She seemed turned on herself, but with our history (I've had a crush on her since 8th grade, and she finds me attractive, but not enough to be together), she seemed to hold back a bit and simply said "...well...when would you like to do this?"
We tried to plan for a few months, but then my girlfriend at the time found out that my friend and I had been hanging out behind her back, and the shit hit the fan. My friend said we would not be able to do this, and we stopped talking about it.
Now in 2014, My friend and I were having one of our typical sex conversations, and she was telling me how she was a dominatrix for a little while. I asked her if she ever fucked anyone with a strap-on. She said she fucked her boss for a few minutes. I asked her to tell me about it. She said it basically did not last long and he was super tight. She fucked him with a 6" strap-on doggystyle, and he shot his cum all over the floor. I asked her to describe what it was like, as I wanted to feel like it was me.
Instead of doing this, she simply told me "Well...We can set something up B. I know you wanted this for a while"
I was giddy like a k** at X-mas. We made our arrangements over the course of a few months: I ordered a 7" strap-on and had it sent to her house, and we set up a date.
I honestly did not know what to expect, as anytime we started talking about it, she approached it like business, by strictly saying "when are you free? we need to hurry up and do this because I can't keep this in my apartment"
We finally agreed on a date (today lol). I went over to her house, nervous as ever. She came to the door, and was fresh out of the shower. Mind you, even though I had been crushing over this girl for 15 years, we never did anything sexual at all. never even kissed. Her hair was still wet, and her nipples were poking through her shirt. She is my perfect woman. She told me to come in and get comfortable. I walked in her room, and she pulled the strap-on out the closet and began to put it on. She is only 4'11", but she is built like the pornstar Pinky, so it made the strap-on look massive on her frame. She asked me if I needed to prep at all. So I walked into the bathroom and looked at myself in the mirror. Damn this is actually going to happen after 6 years of talking about this! I walked out of the bathroom and back to her room. She stood there, tits still poking through her shirt, hair still wet and curly, super thick legs looking righteous, and then that cock hanging real low. Just looking at her had my dick rock-hard, and I almost wanted to flip the script and throw her on the bed, and fuck her until I came deep inside her. She told me to the living room and put a sheet down. She walked in after I did this and brought out some edible lube. She asked "So do you want to suck me off?" I really was not up for this, and feared that she would ask me to do it. I hesitated for a second, and she looked at me and cocked her head to the side and said "boy, get over hear and get on your knees and suck this dick!" I walked over and kneeled down, looking down shaft. I proceed to put it in my mouth, and she was immediately turned on. She started to moan, and told me to keep sucking that dick. I never done anything like this at all. It was humiliating at first, but then it turned me on. She started rubbing my dick with her foot, still moaning just from watching me suck this cock. She then put her hand on my head, and prompted to force the dick further down my throat. I almost choked on it, but she didn't care. I was her bitch, and I loved it. She then abruptly stopped, and told me to turn over and get on all fours and put my ass in the air. I turned over, and just stared at the floor in ecstasy and fear all at the same time. she put the oil in my ass, them started to slide the head in. The immense pressure was mind boggling. I tried to keep my mouth shut and relax. She slowly went back and forth, just trying to loosen up my asshole. finally, she was able to get it in. All I could say was "OH FUCK!" She slide the shaft all the way in, and it surprised her. "Damn B, I can fit it all the way in." She slowly started going back and forth again, this time pushing it all the way in. I was reaching and grabbing for anything to hold on to, but couldn't find anything. My toes were curled, and I could feel the dildo almost up in my stomach. I tapped out, and told her I needed a break. I jumped off the dildo and just turned over, in a daze. She looked at me, asking if I was okay. I replied "yes, just...damn!" She giggled, and asked me to lay on my back. I proceed to do so. She leaned forward, and asked me to cum on her titties. Then she jammed the dildo in my ass. I cried out in ecstasy. I still can't believe this was really happening, especially with my 8th grade crush! She pulled her shirt up and placed my hands on her DD titties. She started to fuck me into oblivion. "You like this dick in your ass huh? You like this fucking dick! You love the way I fuck you, don't you?!?!?" I couldn't say anything besides loud moans and a million curse words. She was going faster, harder, deeper. All of a sudden, she hit something inside me. It felt like she pressed up against my belly button. I started shaking uncontrollably. "Oh my gosh! Oh shit! What the fuck?!?!?!" She grabbed my dick and started jerking it off. The sensation in the tip of my cock was so strong, and with her pressing up against my stomach with the strap-on. She finally calmly said "cum for me baby". All my emotions that I ever had about this girl starting running through my head. I finally felt that I was able to have her, just once, even though I wasn't fucking her myself. I blew my load all over her titties. She kept on fucking me for a few minutes after I came, but I was done. I couldn't take it anymore. She pulled out slowly, and looked at me with a sexy smile on her face. "How was it baby? Did you enjoy yourself?" I sat there speechless, holding onto my stomach. She looked down and asked "Wait what happened?" I said "you fucked me so deep, you were up near my stomach!" She giggled, and said "well, I'm glad you enjoyed it baby, I didn't think I'd have much fun, but I love it".
We both sat there in our sex-funk looking at each other. I wanted to tell her that I did not want this night to end, that I wanted stay with her. I couldn't muster up the courage or energy really to say anything. However, reality started to set in. Her out of state fiancé is coming into town, and they are getting married in 4 days. I am married myself. I have a hall-pass, however my friend does not. We discussed what to do with the strap-on. It was nearly 11p, and her fiancé was about to call. I started to leave her house, and she grabbed me and gave me a big hug, and thanked me for the night that we had.
I will never be with her again, but this experience is something to cherish for years to come.
However, my best female friend apparently had the same interest. One day in 2008, while talking on the phone, she says to me randomly "...so how would you like if I lay you on your back and fuck you with a 12" strap-on?" I was caught off guard, but I immediately was horny. Not knowing what to say, I said "wow...I don't know about that...". She proceeded to say "Come on B, I'll put it in nice and slow. I will go easy on you..." I was ready to bust a nut right then, and I didn't even touch my dick. I downplayed the scenario, wondering if she was being honest or not, and we soon forgot about it.
Fast forward to 2010. I have a long-term girlfriend, who my friend does not necessarily care for. We always talk about sex. Not with each other, but just random sex acts. While in one of our typical conversations, I decide to go all in and throw it out there and asked her "do you still think about strap-on sex?" she said "well...not really. why are you interested?" I told her that yes I was, and that actually I was immediately turned on by what she had told me a few years prior. She seemed turned on herself, but with our history (I've had a crush on her since 8th grade, and she finds me attractive, but not enough to be together), she seemed to hold back a bit and simply said "...well...when would you like to do this?"
We tried to plan for a few months, but then my girlfriend at the time found out that my friend and I had been hanging out behind her back, and the shit hit the fan. My friend said we would not be able to do this, and we stopped talking about it.
Now in 2014, My friend and I were having one of our typical sex conversations, and she was telling me how she was a dominatrix for a little while. I asked her if she ever fucked anyone with a strap-on. She said she fucked her boss for a few minutes. I asked her to tell me about it. She said it basically did not last long and he was super tight. She fucked him with a 6" strap-on doggystyle, and he shot his cum all over the floor. I asked her to describe what it was like, as I wanted to feel like it was me.
Instead of doing this, she simply told me "Well...We can set something up B. I know you wanted this for a while"
I was giddy like a k** at X-mas. We made our arrangements over the course of a few months: I ordered a 7" strap-on and had it sent to her house, and we set up a date.
I honestly did not know what to expect, as anytime we started talking about it, she approached it like business, by strictly saying "when are you free? we need to hurry up and do this because I can't keep this in my apartment"
We finally agreed on a date (today lol). I went over to her house, nervous as ever. She came to the door, and was fresh out of the shower. Mind you, even though I had been crushing over this girl for 15 years, we never did anything sexual at all. never even kissed. Her hair was still wet, and her nipples were poking through her shirt. She is my perfect woman. She told me to come in and get comfortable. I walked in her room, and she pulled the strap-on out the closet and began to put it on. She is only 4'11", but she is built like the pornstar Pinky, so it made the strap-on look massive on her frame. She asked me if I needed to prep at all. So I walked into the bathroom and looked at myself in the mirror. Damn this is actually going to happen after 6 years of talking about this! I walked out of the bathroom and back to her room. She stood there, tits still poking through her shirt, hair still wet and curly, super thick legs looking righteous, and then that cock hanging real low. Just looking at her had my dick rock-hard, and I almost wanted to flip the script and throw her on the bed, and fuck her until I came deep inside her. She told me to the living room and put a sheet down. She walked in after I did this and brought out some edible lube. She asked "So do you want to suck me off?" I really was not up for this, and feared that she would ask me to do it. I hesitated for a second, and she looked at me and cocked her head to the side and said "boy, get over hear and get on your knees and suck this dick!" I walked over and kneeled down, looking down shaft. I proceed to put it in my mouth, and she was immediately turned on. She started to moan, and told me to keep sucking that dick. I never done anything like this at all. It was humiliating at first, but then it turned me on. She started rubbing my dick with her foot, still moaning just from watching me suck this cock. She then put her hand on my head, and prompted to force the dick further down my throat. I almost choked on it, but she didn't care. I was her bitch, and I loved it. She then abruptly stopped, and told me to turn over and get on all fours and put my ass in the air. I turned over, and just stared at the floor in ecstasy and fear all at the same time. she put the oil in my ass, them started to slide the head in. The immense pressure was mind boggling. I tried to keep my mouth shut and relax. She slowly went back and forth, just trying to loosen up my asshole. finally, she was able to get it in. All I could say was "OH FUCK!" She slide the shaft all the way in, and it surprised her. "Damn B, I can fit it all the way in." She slowly started going back and forth again, this time pushing it all the way in. I was reaching and grabbing for anything to hold on to, but couldn't find anything. My toes were curled, and I could feel the dildo almost up in my stomach. I tapped out, and told her I needed a break. I jumped off the dildo and just turned over, in a daze. She looked at me, asking if I was okay. I replied "yes, just...damn!" She giggled, and asked me to lay on my back. I proceed to do so. She leaned forward, and asked me to cum on her titties. Then she jammed the dildo in my ass. I cried out in ecstasy. I still can't believe this was really happening, especially with my 8th grade crush! She pulled her shirt up and placed my hands on her DD titties. She started to fuck me into oblivion. "You like this dick in your ass huh? You like this fucking dick! You love the way I fuck you, don't you?!?!?" I couldn't say anything besides loud moans and a million curse words. She was going faster, harder, deeper. All of a sudden, she hit something inside me. It felt like she pressed up against my belly button. I started shaking uncontrollably. "Oh my gosh! Oh shit! What the fuck?!?!?!" She grabbed my dick and started jerking it off. The sensation in the tip of my cock was so strong, and with her pressing up against my stomach with the strap-on. She finally calmly said "cum for me baby". All my emotions that I ever had about this girl starting running through my head. I finally felt that I was able to have her, just once, even though I wasn't fucking her myself. I blew my load all over her titties. She kept on fucking me for a few minutes after I came, but I was done. I couldn't take it anymore. She pulled out slowly, and looked at me with a sexy smile on her face. "How was it baby? Did you enjoy yourself?" I sat there speechless, holding onto my stomach. She looked down and asked "Wait what happened?" I said "you fucked me so deep, you were up near my stomach!" She giggled, and said "well, I'm glad you enjoyed it baby, I didn't think I'd have much fun, but I love it".
We both sat there in our sex-funk looking at each other. I wanted to tell her that I did not want this night to end, that I wanted stay with her. I couldn't muster up the courage or energy really to say anything. However, reality started to set in. Her out of state fiancé is coming into town, and they are getting married in 4 days. I am married myself. I have a hall-pass, however my friend does not. We discussed what to do with the strap-on. It was nearly 11p, and her fiancé was about to call. I started to leave her house, and she grabbed me and gave me a big hug, and thanked me for the night that we had.
I will never be with her again, but this experience is something to cherish for years to come.
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