I am a straight married man, about 6ft 4in tall which I have been since I was in middle school, in my late 30s. I have always been straight, had various girlfriends before I met my wife. But nobody knows I have had a variaty of same sex encounters.
Youthful expirimenting led me to enjoy anal play when I was pretty young, my wife does know I enjoy it. But what nobody knows is that when I was in highschool a friend was sleeping over, we were both horny as teenagers typically are and decided to JO together. As you can imagine it didn't end there, we jerked eachother, then blew eachother, and it did lead to him penetrating me; though it was just the head and only for a moment. We finished just jerking off, he was awkward afterward and left either in the middle of the night or early before I woke up the next day. I never saw him again after that night.
My next encounter wasn't until I turned 18. I was single and wanted to try it again, but this time I wanted to go all the way. I knew about craigslist personals and decided to give that a shot. I browsed ads and messeged a few that went nowhere, then after a few days of that I came across an ad for a guy in his mid 30s who was 6ft 5in tall who could be described as an otter but not excessively hairy.
We emailed eachother for about a week discussing what I wanted to try and what he liked. He was stable drug and desease free, owned his own home which was well maintained etc. I still considered myself a virgin so this would be my true first time with a man.
I told him I was a virgin and wanted a sensual, erotic experience for my first time which he liked and said he would like that too.
We set a date for me to go over to his house, he said he was going to buy a couple of things for me as a surprise and gifts to celebrate my first time but he wanted me to do a couple of things the day we were to meet to make it the best experience possible. He wanted me smooth shaven from my face down and instructed me how to clean myself out.
The day came and I did as he said, shaved my face and body completly smooth being as thourough as possible, cleaned myself inside and out, looking at myself in the mirror, 6ft 4in tall 145lbs. I got ready and headed to his place. When I got there he greeted me at the door and he was exactly as he described, about 6ft 5in tall with a swimmers body. I went inside and sat on his couch in his living room while he grabbed a couple of beers. When he came back and sat down we talked a bit and got comfortable. We finished our beers and talked a bit more, then when I was laughing about something he reaches over, cups my cheek and says I have a cute laugh. He then leans toward me intending to kiss me but right before he does he tells me im prettier then he imagined.
I blush at the comnent and he leans the rest of the way kissing me. He was kissing me the way I kissed girls, hand on the back of my head, leading the moment. I feel his tongue slip into my mouth as he turns it into a full on makeout session. He pulls up my shirt feeling me up along the way, breaking the kiss to remove my shirt entirely. He says lets take this to the bedroom, leading me by the hand. There is a king size bed with a bag on it, he said that is the surprise he got me.
He said he was going to blindfold me and help me put on his gifts but to keep an open mind once I saw them. I agreed and was blindfolded, I heard some rustleing then i felt him removing my pants, then underwear, and last my socks. I could feel him looking at my freshly smooth body when he said I have a beautiful body. I then felt him touch my chest and slowly move his hand down until he reaches my cock. He notices I am not hard and asks if I am enjoying myself out of concern. I tell him I am but am just nervous. He whispers in my ear that he is glad I am enjoying it, slides his hand down cupping my flacid cock and balls. He says that I am going to feel something cold and hard here, squeezing me, but to bear with him. I feel a cold metalic ring slide over and around my balls, then something similar but felt more like a tube around my cock. As the part slid over my cock I could feel it compressing it making it shorter until I felt something press against the ring around my balls then a *click*. He said that was gift number 1, now for number 2 which is actually 2 parts. After some rustleing he comes back and asks me to lift a foot then the other, I feel very soft fabric sliding up my legs until I feel them get to the top and settle around my waist. He then guides me to the bed and tells me to sit, he grabs a foot and lifts it then I feel some soft fabric again going up my leg then he does the other one. He tells me to stand up and guides me to a spot in the room turning me to face the full length mirror. He is standing very close behind me and whispers remember to keep an open mind and removes my blindfold.
I open my eyes and look into the mirror, I see myself wearing black lacy lingerie. It is a set of some very sexy panties with garters and stockings, I am awestruck. Then I notice the panties don't show any indication of my cock, I reach down and feel my cock pressed between my legs. I move the panties down to get a better look and see it is in a cage compressed down to about 2 inches. If a stranger saw me like this they would absolutely think I was a girl. I feel him press up against me his cock between the cheeks of my pantied butt, reaches around me feeling up my body with one hand pinching a nipple which makes me moan a little, while his other hand slides between my legs rubbing my caged cock. I look at the mirror for a second and see a sexy girl being fondled and enjoying herself.
He asks me if I like his gifts, I nod as I let out another moan from him pressing into my butt again. I gather myself enough to ask about the cage and how I am supposed to cum if I can't touch my cock. He moves his hand from between my legs to my butt, slides a finger between my cheeks ooking my hole over the panties and tells me that I won't be needing to play with my clit today, he is going to show me what it feels like to cum like a girl.
He walks to my side and has me turn so I can see both of us in the mirror leans in and starts making out with me again while grabbing my butt. I put my hand on his bare chest and move down until I find his cock. I am feeling his length, it's about 8in and thick as advertised. There is precum leaking out of it which I gather and use as lube to start stroking him. He breaks the kiss saliva dripping down my chin as we part, he moans and grabs my hand to stop me stroking him. He says we have all day together and he will be cumming in both my pretty mouth, moving his thumb over my lips parting them to suck on it, and in your little pink virgin pussy.
He pulls his thumb out of my mouth and presses down on my shoulders guiding me to my knees. Now on my knees staring at this amazing cock in my face wearing lingerie with a caged cock that was straining to break free but couldn't. He reaches down using his thumb to part my lips again opening my mouth then sliding his cock between them. It is leaking a lot of precum that tastes salty and sweet at the same time. I start sucking and licking slowly feeling him pulse in my mouth. He is moaning but stops me so we can move to the bed. He lays down on his back and tells me to lay next to him on my stomach but angled so I can suck him still. I do as he says and start sucking him again then I feel his hand between my legs again, he says my pussy is wet from my little clitty leaking into my panties. I feel him go underneeth the gusset and start pulling it to the side. Now exposed I can feel the wetness between my legs as he slides his finger from my locked clit to my virgin pussy.
A little moan escapes as he reaches my hole and starts rubbing it softly while I am sucking him. He presses a finger into me using my own precum as lube which allows him to slide in easily. I move my hips to take more of him then he adds another finger, then finally a third. He is finger fucking me then next thing I know his other hand reaches the back of my head and he tells me he is about to cum. He shoots his load into my mouth which I swallow all of. He says good girl and moves his hand from my head to my butt cheek spreading me wider while he is still fingering me. He removes his fingers from me then I feel his breath on my hole and before I knew it he was eating me out making me moan. His cock was hard again and he said I think you're ready. He has me get into doggy tells me what a sexy girl I am, reaching my panties he slides them down to my knees leaving me completly vulnerable. I feel the lube hit my hole then the tip of his cock. He presses forward sliding the head past and as soon as it pops in he leaned forward and whispered "daddys home" into my ear. He fucked me slowly at first then he sped up and he was right I came like a girl. He came in me then plugged me. I went home like that.
Youthful expirimenting led me to enjoy anal play when I was pretty young, my wife does know I enjoy it. But what nobody knows is that when I was in highschool a friend was sleeping over, we were both horny as teenagers typically are and decided to JO together. As you can imagine it didn't end there, we jerked eachother, then blew eachother, and it did lead to him penetrating me; though it was just the head and only for a moment. We finished just jerking off, he was awkward afterward and left either in the middle of the night or early before I woke up the next day. I never saw him again after that night.
My next encounter wasn't until I turned 18. I was single and wanted to try it again, but this time I wanted to go all the way. I knew about craigslist personals and decided to give that a shot. I browsed ads and messeged a few that went nowhere, then after a few days of that I came across an ad for a guy in his mid 30s who was 6ft 5in tall who could be described as an otter but not excessively hairy.
We emailed eachother for about a week discussing what I wanted to try and what he liked. He was stable drug and desease free, owned his own home which was well maintained etc. I still considered myself a virgin so this would be my true first time with a man.
I told him I was a virgin and wanted a sensual, erotic experience for my first time which he liked and said he would like that too.
We set a date for me to go over to his house, he said he was going to buy a couple of things for me as a surprise and gifts to celebrate my first time but he wanted me to do a couple of things the day we were to meet to make it the best experience possible. He wanted me smooth shaven from my face down and instructed me how to clean myself out.
The day came and I did as he said, shaved my face and body completly smooth being as thourough as possible, cleaned myself inside and out, looking at myself in the mirror, 6ft 4in tall 145lbs. I got ready and headed to his place. When I got there he greeted me at the door and he was exactly as he described, about 6ft 5in tall with a swimmers body. I went inside and sat on his couch in his living room while he grabbed a couple of beers. When he came back and sat down we talked a bit and got comfortable. We finished our beers and talked a bit more, then when I was laughing about something he reaches over, cups my cheek and says I have a cute laugh. He then leans toward me intending to kiss me but right before he does he tells me im prettier then he imagined.
I blush at the comnent and he leans the rest of the way kissing me. He was kissing me the way I kissed girls, hand on the back of my head, leading the moment. I feel his tongue slip into my mouth as he turns it into a full on makeout session. He pulls up my shirt feeling me up along the way, breaking the kiss to remove my shirt entirely. He says lets take this to the bedroom, leading me by the hand. There is a king size bed with a bag on it, he said that is the surprise he got me.
He said he was going to blindfold me and help me put on his gifts but to keep an open mind once I saw them. I agreed and was blindfolded, I heard some rustleing then i felt him removing my pants, then underwear, and last my socks. I could feel him looking at my freshly smooth body when he said I have a beautiful body. I then felt him touch my chest and slowly move his hand down until he reaches my cock. He notices I am not hard and asks if I am enjoying myself out of concern. I tell him I am but am just nervous. He whispers in my ear that he is glad I am enjoying it, slides his hand down cupping my flacid cock and balls. He says that I am going to feel something cold and hard here, squeezing me, but to bear with him. I feel a cold metalic ring slide over and around my balls, then something similar but felt more like a tube around my cock. As the part slid over my cock I could feel it compressing it making it shorter until I felt something press against the ring around my balls then a *click*. He said that was gift number 1, now for number 2 which is actually 2 parts. After some rustleing he comes back and asks me to lift a foot then the other, I feel very soft fabric sliding up my legs until I feel them get to the top and settle around my waist. He then guides me to the bed and tells me to sit, he grabs a foot and lifts it then I feel some soft fabric again going up my leg then he does the other one. He tells me to stand up and guides me to a spot in the room turning me to face the full length mirror. He is standing very close behind me and whispers remember to keep an open mind and removes my blindfold.
I open my eyes and look into the mirror, I see myself wearing black lacy lingerie. It is a set of some very sexy panties with garters and stockings, I am awestruck. Then I notice the panties don't show any indication of my cock, I reach down and feel my cock pressed between my legs. I move the panties down to get a better look and see it is in a cage compressed down to about 2 inches. If a stranger saw me like this they would absolutely think I was a girl. I feel him press up against me his cock between the cheeks of my pantied butt, reaches around me feeling up my body with one hand pinching a nipple which makes me moan a little, while his other hand slides between my legs rubbing my caged cock. I look at the mirror for a second and see a sexy girl being fondled and enjoying herself.
He asks me if I like his gifts, I nod as I let out another moan from him pressing into my butt again. I gather myself enough to ask about the cage and how I am supposed to cum if I can't touch my cock. He moves his hand from between my legs to my butt, slides a finger between my cheeks ooking my hole over the panties and tells me that I won't be needing to play with my clit today, he is going to show me what it feels like to cum like a girl.
He walks to my side and has me turn so I can see both of us in the mirror leans in and starts making out with me again while grabbing my butt. I put my hand on his bare chest and move down until I find his cock. I am feeling his length, it's about 8in and thick as advertised. There is precum leaking out of it which I gather and use as lube to start stroking him. He breaks the kiss saliva dripping down my chin as we part, he moans and grabs my hand to stop me stroking him. He says we have all day together and he will be cumming in both my pretty mouth, moving his thumb over my lips parting them to suck on it, and in your little pink virgin pussy.
He pulls his thumb out of my mouth and presses down on my shoulders guiding me to my knees. Now on my knees staring at this amazing cock in my face wearing lingerie with a caged cock that was straining to break free but couldn't. He reaches down using his thumb to part my lips again opening my mouth then sliding his cock between them. It is leaking a lot of precum that tastes salty and sweet at the same time. I start sucking and licking slowly feeling him pulse in my mouth. He is moaning but stops me so we can move to the bed. He lays down on his back and tells me to lay next to him on my stomach but angled so I can suck him still. I do as he says and start sucking him again then I feel his hand between my legs again, he says my pussy is wet from my little clitty leaking into my panties. I feel him go underneeth the gusset and start pulling it to the side. Now exposed I can feel the wetness between my legs as he slides his finger from my locked clit to my virgin pussy.
A little moan escapes as he reaches my hole and starts rubbing it softly while I am sucking him. He presses a finger into me using my own precum as lube which allows him to slide in easily. I move my hips to take more of him then he adds another finger, then finally a third. He is finger fucking me then next thing I know his other hand reaches the back of my head and he tells me he is about to cum. He shoots his load into my mouth which I swallow all of. He says good girl and moves his hand from my head to my butt cheek spreading me wider while he is still fingering me. He removes his fingers from me then I feel his breath on my hole and before I knew it he was eating me out making me moan. His cock was hard again and he said I think you're ready. He has me get into doggy tells me what a sexy girl I am, reaching my panties he slides them down to my knees leaving me completly vulnerable. I feel the lube hit my hole then the tip of his cock. He presses forward sliding the head past and as soon as it pops in he leaned forward and whispered "daddys home" into my ear. He fucked me slowly at first then he sped up and he was right I came like a girl. He came in me then plugged me. I went home like that.
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