Afterhours22
Literotica Guru
- Joined
- Oct 16, 2006
- Posts
- 1,121
I recently had a fantastic time with a beautiful crossdressing friend of mine. Before our date, I had no idea that he was. I did know that he was gay and that him and I were going to get together for some fun... Wow! I didn't know how much fun I was going to have with "her."
It had been a number of years since I was last with a man, close to 30 years to be exact, and I have been getting to the point where I really wanted to experiment and find someone to play with. I was introduced to a guy; I’ll call Danni for this true story, about a year ago. I knew Danni was gay because he was very open about it and I respected him for being true to himself. Now Danni was a very good looking feminine guy, standing only about 5’7”, with straight dark hair and a light reddish brown skin tone.
So after being friends with Danni this long, I decided it was time to confide in him about my bisexuality that I have been hiding for so many years now. We were talking on the phone and when I told him about it, he just giggled and said that he had a feeling I was hiding something. I told him that I really would like to find a playmate but I was very nervous about looking and very scared of what I my get myself in to. Well, Danni, being the great friend and all, told me that he would be happy to volunteer himself, because he had secretly been attracted to me for some time now, but out of respect and not wanting to endanger our friendship by just “coming” on to me. So we talked about our likes a little bit and agreed on a day for him to come over and Danni said that he had a special surprise for me. I couldn’t wait.
The day came, and I was so nervous that whole day in anticipation of Danni’s arrival, that I must have cleaned the house 3 times over. I just sat down with my 2nd glass of wine when there was a soft knock on my door. When I opened it, I could not believe my eyes. There was Danni in all his glory, dressed head to toe as a woman. He looked at me and said, “Surprise!”
I was just amazed at how beautiful he looked and I just stood there dumbfounded. He then said, “You going to invite me in or am I just going to suck your cock right here?” That shook me back to reality and I led him in to the living room, and handed him a glass of chardonnay as we sat down, facing each other on my sectional. I couldn’t keep my eyes off of him as we sat there and made small talk. He had a short black leather skirt on, a silky dark red blouse, stockings and stiletto heels. His hair was naturally long, so he just had it done up with some soft curl to his long locks. He was absolutely gorgeous and I just came out and told him, “Danni, you look incredible!” He smiled, stood up, then came over to me, bent over and kissed me. Now kissing another man had never been something I was really in to but I just flowed right into it with Danni. He kissed me so softly at first and once I responded to it, we then began kissing more passionately. I pulled him down with me on the cushion, and our hands were already roaming over each other. He reached down and started rubbing my already stiffening cock through my jeans as my hands wrapped around his tight ass. At that point, we were both in motion enjoying the feel of each other. Danni then pulled away from our kiss, pulled my shirt over my head and ran his fingers through my chest hair, tracing all around my nipples and making his way down across my stomach to the top of my jeans. He then unbuttoned them, slowly pulled the zipper down and released my blood engorged cock. I caught my breath in my throat as his delicate hands slowly moved all over my hard erection, from the base to the tip. He then slid down to the floor in front of me and started tracing his tongue up and down and around my swollen cock head. I was in heaven, laying there just breathing heavy, letting out my soft moans of delight. His tongue dipped in my cock hole and scooped out the already flowing precum from it. He then kissed the tip and slowly opened his mouth letting just a little bit of my cock in then further and further he went down, taking almost my entire 6 ½” cock in. Then he began moving up and down on it, sucking me hard, and working magic on me with his tongue. With one hand on the base of my cock and the other softly massaging my balls, Danni was giving me the best blowjob I had ever had in my entire life. I couldn’t believe how wonderful he felt and I began to feel my impending orgasm. I told Danni this and I wanted to hold up a bit.
So I pulled him up, kissed him again and motioned for him to take my place on the sofa. Continuing to kiss him, I helped unbutton his blouse, running my hands inside against his soft skin. Then kneeling down in front of him, I slowly pushed his skirt up, revealing his stocking tops, then finally uncovering his black silky panty cover cock, already trying to find its way out. I looked up at Danni and said to him, “Danni, it’s been a very long time since I have done this, so I hope I do okay.” He just smiled and said, “I’m sure you will be wonderful.”
He then lifted his ass a bit to help me as I pulled his panties down, revealing the true splendor of his cock. It was gorgeous, too. A full cut 8 inches long, but more slender compared to my thick cock. I took it in my hand and just reveled in the feel of it. It was so smooth and soft, like running my hands over the finest silk material. I moved my hands up and down as he lay back with his eyes closed enjoy my touch. I move my mouth closer to it as my fingers dipped in to the flowing precum around the tip of his cock, and put them into my mouth. Oh he tasted so good. I could not hold back any longer and in one smooth motion, I engulfed his hard cock all the way back to my throat and held it there for just a second until I could feel my gag reflex kick in a little. Danni, his head back and eyes closed, groaned his pleasure as my mouth wrapped around his throbbing cock. I could not believe I waited this long to enjoy this again. In almost an instant, I was addicted once more to sucking cock. I worked as well as I thought I could on him, taking him in deep over and over again, trying to put my gag reflex down so I could get every inch of that beautiful cock in my mouth and throat. Danni, between his soft moans, told me that I was wonderful and he loved my mouth on his cock. As I sucked him up and down, I used my now saliva lubricated hand to massage his prick right along with my lips and tongue. Danni’s cock really began to throb and I knew he was close to cumming. I lifted my mouth from him briefly telling him, “Give me your cum, baby.”
He was breathing and moaning faster and faster, his legs starting to shake. Then I felt his cock pulsate hard and the first stream of cum hit the back of my throat as Danni cried out. I continued sucking hard on him, swallowing as fast as I could to keep up with his flow. He had a lot of cum and I wasn’t about to lose a drop. Mmmmm he tasted heavenly, too. I’ve never tasted cum so good as his was. I kept his cock in my mouth as he slowly came down and his cum stopped flowing. He jerked in post orgasmic bliss as I held him there, my lips sealed around his cock head and my tongue swirling around to get any remaining drops of his sweet cum. Danni opened his eyes and smiled at me. “Oh my God, you are wonderful,” he said. “That felt absolutely incredible!”
I released his softening cock from my lips, and climbed up beside him, kissing him once more, ever so softly. “I’m very happy you liked it,” I said, “It’s been a long time and wasn’t sure if I was going to do good for you.” Danni looked at me in the eyes and said, “Liked it?” “Oh my God, I loved it!” “You and I are going to have so much fun.” Danni reached down into his bad and pulled out a bottle of lube, then opened it and poured some on his hands. He then rubbed it all over my still hard cock, covering it completely. Danni looked to me and said, “Hon, I’ve never been with another man bareback, and I was wondering if you would fuck me and give me your cum in my ass?” I smiled and shook my head yes and kissed him passionately.
He then stood and rubbed a generous amount of lube around his ass, while straddling and facing me. He then reached down and grabbed my cock, aiming it into the crack of his sweet ass. He had his eyes closed and I could feel the tip of my cock pressing against his opening briefly, then slipping in to his hot depths, until my balls touched his ass cheeks. Danni groaned out loud and I was in heaven at how wonderful and tight his ass was wrapped around my cock. He began moving up and down on me, slowly at first then building into a nice smooth pace. For not being a “virgin” back there, I could not believe how tight his ass felt on me. Danni moaned, “God I love how your hot cock feels in me,” as he continued to ride me faster and faster, my hands holding on to his sides for dear life. I knew I wasn’t going to last long as my cum had already been idled deep in my shaft since he was sucking my cock earlier. “Oh my, Danni, I’m going to cum baby,” I said to him as he slammed his ass up and down on me harder. “Yes, cum in me baby!” he exclaimed. The first wave hit me hard and I grabbed on to him even harder, slamming my cock all the way into his rectum as far as it would go, releasing my hot cum into him! Over and over the pulsating throbbing hit me with each wave, nearly causing us to fall off the sofa. He bent down to kiss me and I pulled him close to me and held him tight.
We stayed like that for a bit, and then finally he moved off of me. He reached back, scooped some of my cum leaking from his ass and put it in his mouth. “Mmmmm, I love your cum, honey.” He said to me. He then excused himself to go cleanup as I sat there in total bliss, looking down at my soft spent cock.
Danni and I had a few more glasses of wine and talked the night away. He spent the night with me and we fell asleep in each other’s arms. We parted ways the next day after a hot shower together and a nice breakfast, knowing this was the beginning of something very special. I think I am in love.
It had been a number of years since I was last with a man, close to 30 years to be exact, and I have been getting to the point where I really wanted to experiment and find someone to play with. I was introduced to a guy; I’ll call Danni for this true story, about a year ago. I knew Danni was gay because he was very open about it and I respected him for being true to himself. Now Danni was a very good looking feminine guy, standing only about 5’7”, with straight dark hair and a light reddish brown skin tone.
So after being friends with Danni this long, I decided it was time to confide in him about my bisexuality that I have been hiding for so many years now. We were talking on the phone and when I told him about it, he just giggled and said that he had a feeling I was hiding something. I told him that I really would like to find a playmate but I was very nervous about looking and very scared of what I my get myself in to. Well, Danni, being the great friend and all, told me that he would be happy to volunteer himself, because he had secretly been attracted to me for some time now, but out of respect and not wanting to endanger our friendship by just “coming” on to me. So we talked about our likes a little bit and agreed on a day for him to come over and Danni said that he had a special surprise for me. I couldn’t wait.
The day came, and I was so nervous that whole day in anticipation of Danni’s arrival, that I must have cleaned the house 3 times over. I just sat down with my 2nd glass of wine when there was a soft knock on my door. When I opened it, I could not believe my eyes. There was Danni in all his glory, dressed head to toe as a woman. He looked at me and said, “Surprise!”
I was just amazed at how beautiful he looked and I just stood there dumbfounded. He then said, “You going to invite me in or am I just going to suck your cock right here?” That shook me back to reality and I led him in to the living room, and handed him a glass of chardonnay as we sat down, facing each other on my sectional. I couldn’t keep my eyes off of him as we sat there and made small talk. He had a short black leather skirt on, a silky dark red blouse, stockings and stiletto heels. His hair was naturally long, so he just had it done up with some soft curl to his long locks. He was absolutely gorgeous and I just came out and told him, “Danni, you look incredible!” He smiled, stood up, then came over to me, bent over and kissed me. Now kissing another man had never been something I was really in to but I just flowed right into it with Danni. He kissed me so softly at first and once I responded to it, we then began kissing more passionately. I pulled him down with me on the cushion, and our hands were already roaming over each other. He reached down and started rubbing my already stiffening cock through my jeans as my hands wrapped around his tight ass. At that point, we were both in motion enjoying the feel of each other. Danni then pulled away from our kiss, pulled my shirt over my head and ran his fingers through my chest hair, tracing all around my nipples and making his way down across my stomach to the top of my jeans. He then unbuttoned them, slowly pulled the zipper down and released my blood engorged cock. I caught my breath in my throat as his delicate hands slowly moved all over my hard erection, from the base to the tip. He then slid down to the floor in front of me and started tracing his tongue up and down and around my swollen cock head. I was in heaven, laying there just breathing heavy, letting out my soft moans of delight. His tongue dipped in my cock hole and scooped out the already flowing precum from it. He then kissed the tip and slowly opened his mouth letting just a little bit of my cock in then further and further he went down, taking almost my entire 6 ½” cock in. Then he began moving up and down on it, sucking me hard, and working magic on me with his tongue. With one hand on the base of my cock and the other softly massaging my balls, Danni was giving me the best blowjob I had ever had in my entire life. I couldn’t believe how wonderful he felt and I began to feel my impending orgasm. I told Danni this and I wanted to hold up a bit.
So I pulled him up, kissed him again and motioned for him to take my place on the sofa. Continuing to kiss him, I helped unbutton his blouse, running my hands inside against his soft skin. Then kneeling down in front of him, I slowly pushed his skirt up, revealing his stocking tops, then finally uncovering his black silky panty cover cock, already trying to find its way out. I looked up at Danni and said to him, “Danni, it’s been a very long time since I have done this, so I hope I do okay.” He just smiled and said, “I’m sure you will be wonderful.”
He then lifted his ass a bit to help me as I pulled his panties down, revealing the true splendor of his cock. It was gorgeous, too. A full cut 8 inches long, but more slender compared to my thick cock. I took it in my hand and just reveled in the feel of it. It was so smooth and soft, like running my hands over the finest silk material. I moved my hands up and down as he lay back with his eyes closed enjoy my touch. I move my mouth closer to it as my fingers dipped in to the flowing precum around the tip of his cock, and put them into my mouth. Oh he tasted so good. I could not hold back any longer and in one smooth motion, I engulfed his hard cock all the way back to my throat and held it there for just a second until I could feel my gag reflex kick in a little. Danni, his head back and eyes closed, groaned his pleasure as my mouth wrapped around his throbbing cock. I could not believe I waited this long to enjoy this again. In almost an instant, I was addicted once more to sucking cock. I worked as well as I thought I could on him, taking him in deep over and over again, trying to put my gag reflex down so I could get every inch of that beautiful cock in my mouth and throat. Danni, between his soft moans, told me that I was wonderful and he loved my mouth on his cock. As I sucked him up and down, I used my now saliva lubricated hand to massage his prick right along with my lips and tongue. Danni’s cock really began to throb and I knew he was close to cumming. I lifted my mouth from him briefly telling him, “Give me your cum, baby.”
He was breathing and moaning faster and faster, his legs starting to shake. Then I felt his cock pulsate hard and the first stream of cum hit the back of my throat as Danni cried out. I continued sucking hard on him, swallowing as fast as I could to keep up with his flow. He had a lot of cum and I wasn’t about to lose a drop. Mmmmm he tasted heavenly, too. I’ve never tasted cum so good as his was. I kept his cock in my mouth as he slowly came down and his cum stopped flowing. He jerked in post orgasmic bliss as I held him there, my lips sealed around his cock head and my tongue swirling around to get any remaining drops of his sweet cum. Danni opened his eyes and smiled at me. “Oh my God, you are wonderful,” he said. “That felt absolutely incredible!”
I released his softening cock from my lips, and climbed up beside him, kissing him once more, ever so softly. “I’m very happy you liked it,” I said, “It’s been a long time and wasn’t sure if I was going to do good for you.” Danni looked at me in the eyes and said, “Liked it?” “Oh my God, I loved it!” “You and I are going to have so much fun.” Danni reached down into his bad and pulled out a bottle of lube, then opened it and poured some on his hands. He then rubbed it all over my still hard cock, covering it completely. Danni looked to me and said, “Hon, I’ve never been with another man bareback, and I was wondering if you would fuck me and give me your cum in my ass?” I smiled and shook my head yes and kissed him passionately.
He then stood and rubbed a generous amount of lube around his ass, while straddling and facing me. He then reached down and grabbed my cock, aiming it into the crack of his sweet ass. He had his eyes closed and I could feel the tip of my cock pressing against his opening briefly, then slipping in to his hot depths, until my balls touched his ass cheeks. Danni groaned out loud and I was in heaven at how wonderful and tight his ass was wrapped around my cock. He began moving up and down on me, slowly at first then building into a nice smooth pace. For not being a “virgin” back there, I could not believe how tight his ass felt on me. Danni moaned, “God I love how your hot cock feels in me,” as he continued to ride me faster and faster, my hands holding on to his sides for dear life. I knew I wasn’t going to last long as my cum had already been idled deep in my shaft since he was sucking my cock earlier. “Oh my, Danni, I’m going to cum baby,” I said to him as he slammed his ass up and down on me harder. “Yes, cum in me baby!” he exclaimed. The first wave hit me hard and I grabbed on to him even harder, slamming my cock all the way into his rectum as far as it would go, releasing my hot cum into him! Over and over the pulsating throbbing hit me with each wave, nearly causing us to fall off the sofa. He bent down to kiss me and I pulled him close to me and held him tight.
We stayed like that for a bit, and then finally he moved off of me. He reached back, scooped some of my cum leaking from his ass and put it in his mouth. “Mmmmm, I love your cum, honey.” He said to me. He then excused himself to go cleanup as I sat there in total bliss, looking down at my soft spent cock.
Danni and I had a few more glasses of wine and talked the night away. He spent the night with me and we fell asleep in each other’s arms. We parted ways the next day after a hot shower together and a nice breakfast, knowing this was the beginning of something very special. I think I am in love.
... Aaaww - you're all loved up aren't you?! Big smile here 
