My Best Friend.
I had been cross dressing since I was about ************, Iâm now in my thirties and this story is about my first encounter with another man. It all started one day when my wife would be out for the day and I had settled down to surf the net looking for transgender sites, I was only dressed in a black lace garter belt, black hose and high heeled black pumps. I had just found a promising site and my cock was getting hard, as I started jerking off the phone rang, I almost decided to ignore it but luckily I answered it.
It was my best friend Ross, he was working on his car and needed a hand as he couldnât hold the part in place and tighten the nuts at the same time, his wife Barbara, a nurse, was at work and he asked if I could help him out, he assured me it would only take a few minutes and only living a short distance away I said I would be there in a few minutes. Thinking I would be back soon to the Tran gendered honeys I decided to just throw on a pair of jeans, T shirt and a pair of sneakers Instead of getting changed. I drove over to Rossâs house and found him under his car he thanked me for coming to help and showed me what needed doing. As he held the part in place I reached over the front fender and tightened the nuts. It only took a few seconds and Ross climbed out from under the car inviting me in for a beer as he went to get cleaned up, I got 2 beers from the refrigerator and sat at the kitchen table, Ross returned from the bathroom and sat down and took a long swig from his beer and I noticed him staring at me. I asked him what was wrong and he asked me how long had I been wearing womenâs underwear, my heart leapt into my throat and a thousand things started going through my mind, how did he know, I donât know what your talking about, I answered.
He said I got a good look at your ankles whilst I was under the car, I saw you were wearing pantyhose, How stupid could I be, Ross could tell from the look on my face I had been caught out, but he reassured me that he was cool with it and not to worry as he would keep my little secret.
We got to talking about how I started dressing up and how good it made me feel when I jerked off or on the rare occasion fucked my wife whilst wearing a bra, stockings/pantyhose and high heels. Ross then asked if he could see what I was wearing now, I was a bit apprehensive but without thinking too much about it I thought âwhy the fuck notâ, I took off the T shirt, undid my jeans pulling them down as I kicked off my sneakers and there I was standing in front of my best friend wearing just black hose and black garter belt, my cock semi hard from all the talk about sex and dressing up.
Ross stood and looked at me for a few moments and said I looked sexy and he just had to try this himself, he said his wife didnât have any stockings, but being a nurse she had a ready supply of pantyhose, I told him I preferred pantyhose, as they feel great on my hips and ass, but they restrict access to my cock when Iâm jerking off, I told him to get a pair of hose and I would cut a hole in the front for his cock and balls so he could jerk off.
I had never really thought about sex with another guy, but watching Ross strip off and put the tan hose on gave me an enormous boner, especially when I saw his cock which was about the same as mine, about 7 inches, I knelt down behind Ross and helped him pull up the hose, running my hands up and down his legs and butt. He said this feels fantastic and he loved the feeling of my hands rubbing him, he turned around and started jerking his cock and said he wouldnât last long at this rate.
I grabbed his hand to stop him and pulled his hand away from his cock and without thinking I opened my mouth and took his cock into my mouth and started to suck him off. I couldnât believe I was dressed in a garter and hose, on my knees sucking my friendâs cock, whilst he had on a pair of his wifeâs pantyhose.
Ross came quickly, filling my mouth with his hot cum and I swallowed the lot, I sat back on my heels contemplating what I had just done and where our friendship would go now, when Ross suggested we go to the bedroom and get comfortable whilst he repaid the favour, I didnât hesitate for a second and we were soon on the bed, Ross sucking my cock like a pro.
Ross was doing a great job and I was getting ready to blow when we heard a gasp and a âwhat the fuck are you pair doingâ
It was Rossâs wife Barbara home early from work standing in the doorway in her nurses uniform. I almost died and crawled up my own ass, but Ross stood up and said âwhat does it look like Iâm wearing your hose and sucking Timâs cock and you better get your uniform off and join me before he cumsâ
Barbara undid the zip in the front of her uniform letting it fall to the ground and wearing just a white lace bra and white pantyhose she moved to the bed and joined her husband in sucking my cock, sharing it like two k**s with one ice cream cone.
As Barbara continued sucking my cock and balls Ross ripped her pantyhose giving him access to her cunt , as he started to lick her out I took Rossâs cock back in my mouth and competed the daisy chain, all of us sucking and licking each other.
After we had all cum Ross wanted to fuck Barbara and I had an idea, I got Ross to lie on his back at the corner of the bed with his feet still on the floor and then Barbara with her back to Ross and straddle his cock and lean back onto Rossâs chest, this exposed their cock and cunt and I got on my knees and started licking Rossâs balls and shaft as it plunged into Barbaraâs hot cunt and when I started to lick her labia and clit Barbara exploded and bucked up and down on Rossâs shaft for all she was worth, Ross started to cum as Barbaraâs orgasm subsided and he shot his load into her steaming box and I pulled Rossâs shrinking prick into my mouth and sucked and licked all of their cum.
For the rest of the afternoon we sucked and fucked every which way including both of us fucking Barbara, a double penetration where Ross fucked her up the ass for the first time and where Ross fucked me up the ass whilst Barbara sucked my cock. But thatâs another story.
It was my best friend Ross, he was working on his car and needed a hand as he couldnât hold the part in place and tighten the nuts at the same time, his wife Barbara, a nurse, was at work and he asked if I could help him out, he assured me it would only take a few minutes and only living a short distance away I said I would be there in a few minutes. Thinking I would be back soon to the Tran gendered honeys I decided to just throw on a pair of jeans, T shirt and a pair of sneakers Instead of getting changed. I drove over to Rossâs house and found him under his car he thanked me for coming to help and showed me what needed doing. As he held the part in place I reached over the front fender and tightened the nuts. It only took a few seconds and Ross climbed out from under the car inviting me in for a beer as he went to get cleaned up, I got 2 beers from the refrigerator and sat at the kitchen table, Ross returned from the bathroom and sat down and took a long swig from his beer and I noticed him staring at me. I asked him what was wrong and he asked me how long had I been wearing womenâs underwear, my heart leapt into my throat and a thousand things started going through my mind, how did he know, I donât know what your talking about, I answered.
He said I got a good look at your ankles whilst I was under the car, I saw you were wearing pantyhose, How stupid could I be, Ross could tell from the look on my face I had been caught out, but he reassured me that he was cool with it and not to worry as he would keep my little secret.
We got to talking about how I started dressing up and how good it made me feel when I jerked off or on the rare occasion fucked my wife whilst wearing a bra, stockings/pantyhose and high heels. Ross then asked if he could see what I was wearing now, I was a bit apprehensive but without thinking too much about it I thought âwhy the fuck notâ, I took off the T shirt, undid my jeans pulling them down as I kicked off my sneakers and there I was standing in front of my best friend wearing just black hose and black garter belt, my cock semi hard from all the talk about sex and dressing up.
Ross stood and looked at me for a few moments and said I looked sexy and he just had to try this himself, he said his wife didnât have any stockings, but being a nurse she had a ready supply of pantyhose, I told him I preferred pantyhose, as they feel great on my hips and ass, but they restrict access to my cock when Iâm jerking off, I told him to get a pair of hose and I would cut a hole in the front for his cock and balls so he could jerk off.
I had never really thought about sex with another guy, but watching Ross strip off and put the tan hose on gave me an enormous boner, especially when I saw his cock which was about the same as mine, about 7 inches, I knelt down behind Ross and helped him pull up the hose, running my hands up and down his legs and butt. He said this feels fantastic and he loved the feeling of my hands rubbing him, he turned around and started jerking his cock and said he wouldnât last long at this rate.
I grabbed his hand to stop him and pulled his hand away from his cock and without thinking I opened my mouth and took his cock into my mouth and started to suck him off. I couldnât believe I was dressed in a garter and hose, on my knees sucking my friendâs cock, whilst he had on a pair of his wifeâs pantyhose.
Ross came quickly, filling my mouth with his hot cum and I swallowed the lot, I sat back on my heels contemplating what I had just done and where our friendship would go now, when Ross suggested we go to the bedroom and get comfortable whilst he repaid the favour, I didnât hesitate for a second and we were soon on the bed, Ross sucking my cock like a pro.
Ross was doing a great job and I was getting ready to blow when we heard a gasp and a âwhat the fuck are you pair doingâ
It was Rossâs wife Barbara home early from work standing in the doorway in her nurses uniform. I almost died and crawled up my own ass, but Ross stood up and said âwhat does it look like Iâm wearing your hose and sucking Timâs cock and you better get your uniform off and join me before he cumsâ
Barbara undid the zip in the front of her uniform letting it fall to the ground and wearing just a white lace bra and white pantyhose she moved to the bed and joined her husband in sucking my cock, sharing it like two k**s with one ice cream cone.
As Barbara continued sucking my cock and balls Ross ripped her pantyhose giving him access to her cunt , as he started to lick her out I took Rossâs cock back in my mouth and competed the daisy chain, all of us sucking and licking each other.
After we had all cum Ross wanted to fuck Barbara and I had an idea, I got Ross to lie on his back at the corner of the bed with his feet still on the floor and then Barbara with her back to Ross and straddle his cock and lean back onto Rossâs chest, this exposed their cock and cunt and I got on my knees and started licking Rossâs balls and shaft as it plunged into Barbaraâs hot cunt and when I started to lick her labia and clit Barbara exploded and bucked up and down on Rossâs shaft for all she was worth, Ross started to cum as Barbaraâs orgasm subsided and he shot his load into her steaming box and I pulled Rossâs shrinking prick into my mouth and sucked and licked all of their cum.
For the rest of the afternoon we sucked and fucked every which way including both of us fucking Barbara, a double penetration where Ross fucked her up the ass for the first time and where Ross fucked me up the ass whilst Barbara sucked my cock. But thatâs another story.
12 years ago
