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Old 03-18-2013, 01:01 PM   #1
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A recent experience with a gorgeous Crossdresser..

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.
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Old 03-18-2013, 01:22 PM   #2
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Thunderous applause!! Good for you and great to hear a happy story ... Aaaww - you're all loved up aren't you?! Big smile here
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Old 03-19-2013, 11:08 AM   #3
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Thunderous applause!! Good for you and great to hear a happy story ... Aaaww - you're all loved up aren't you?! Big smile here
Thank you! Yes I sure am! Can't wait until this coming weekend when Danni come back in town. We have a date!
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Old 03-19-2013, 09:17 PM   #4
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Thank you! Yes I sure am! Can't wait until this coming weekend when Danni come back in town. We have a date!
I loved your story and can not wait to hear what happened the next time. I have had a few experiences similar to that but it has been a while. Too long.
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Old 03-21-2013, 10:51 AM   #5
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Definitely....

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I loved your story and can not wait to hear what happened the next time. I have had a few experiences similar to that but it has been a while. Too long.
I will share the fun for sure!
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Old 03-21-2013, 12:49 PM   #6
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I will share the fun for sure!
Are you going to submit it to the stories section? You should!
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Old 03-22-2013, 12:16 PM   #7
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I tried to....

but they keep rejecting it because of improper quotes and such.... so I just gave up on it... I never had any trouble at all with my other stories... I guess they want professionally written stories now. IDK

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Are you going to submit it to the stories section? You should!
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Old 03-25-2013, 11:36 AM   #8
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More!!!!
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Old 03-25-2013, 11:53 AM   #9
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We met up again this past Saurday..

details to follow...... If I can quick jacking off long enough to write about it....

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More!!!!
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Old 03-25-2013, 04:40 PM   #10
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details to follow...... If I can quick jacking off long enough to write about it....
my panties are wet already!
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Old 03-25-2013, 06:38 PM   #11
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mmmmm

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my panties are wet already!
Yummy..
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Old 03-25-2013, 10:00 PM   #12
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hmm sounds wonderful, cant wait to hear more
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Old 03-26-2013, 11:47 AM   #13
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more fun with Danni...

Danni and I met up again this past weekend and again, "she" literally rocked my entire fucking world. Coming in wearing a tight jean skirt, a loose black top and heels. Knowing what we already wanted and needed, she hardly got in the door and we were all over each other, kissing passionately, our hands roaming all over each other. Hungry for her cock, I then dropped down right there, lifting her skirt to reveal her sexy red panties, pulled them down to release her rapidly hardening cock right in to my mouth. I was in a cock sucking frenzy at first, not being able to get enough of her. Danni was running her fingers through my hair, moaning her lust for the pleasure I was giving her. I then slowed into a nice steady rhythm going up and down on her, going almost 3/4 of the way down her shaft before feeling my gag reflex kicking in. My hand now wet with saliva, started working in sync with my mouth, giving her a complete cock massage from the head to the base, my other hand cupping and massaging her gorgeous shaved balls. Danni started getting into rhythm with me, just slightly thrusting her hips forward each time I went down, slowly at first then moving a little faster. Her cock was throbbing in my mouth and I knew it wouldn't be long before she gave me her hot liquid love. Moaning very loud now, Danni called out my name and said she was going to cum. Her cock gave a little jerk and the first jet of hot cum squirted to the back of my throat. I sucked harder but slowed my pace a bit in time with each pulse of semen flowing into my hungry mouth. Oh my God, she tasted heavenly. I kept sucking until the last drop was gone, looking up and Danni, and her looking down at me smiling and groaning her approval.

Danni could no longer stand, leaning back against the wall and slowly sliding down to the floor with me. I wrapped my arms around her and kissed her ever so softly. We stayed there for a short time just enjoying her orgasmic afterglow. Shortly thereafter we made our way over to the sofa, where we continued to kiss and explore each other, helping each other undress completely. Danni kissed her way down my chest and stomach, her hands massaging and stroking my very hard and dripping cock. Looking at the tip of my cock, she stuck her tongue to it and dipping inside the hole, pulling back a generous amount of precum to her mouth. Then opening up and taking the head inside. Swirling her tongue around it and then sucking all the way down, my cock going into her throat. She held it there for a few seconds before slowly backing up to the top. My GOD she was a cock master! I was in total bliss laying back with my eyes closed when I felt her fingers making their way down below my balls, moving towards my asshole. More moans escaped me as she started circling her fingers around my entrance. Stopping briefly, releasing my cock from her mouth, to reach over to the end stand for some lubricant, (yes I was prepared) and after putting a generous amount on her fingers, back to my asshole they went. Taking my cock back into her sucking mouth, she began sliding one finger at a time inside my tight hole. It felt amazing! Danni then asked me to turn over so she could get better access. Now face down on the sofa with my knees on the floor, Danni return her fingers in to my ass, moving gently in and out then settling on the area of my prostrate. Massaging inside me while her other hand reached between and was playing with my cock and balls. I was in pure heaven, eyes closed face down ass up toward her and her magic hands.

She pulled her fingers out, leaving me feeling empty but only for an instant. The next thing I knew, I felt the head of her cock sliding against my ass cheek, once more fully erect. The tip found my opening and pressed it's way inside. Oh my GOD what a feeling! No pain at all thanks to her massage, only pure unbridled pleasure as her cock made it's way all the way inside until I fel her balls rest on me. She asked me if I was okay and I just moaned out a yes... oh God yes.. She began moving inside me slowly in and out then moving into a slightly faster motion... fucking me over and over again. I felt like a cock whore in heat, moaning and groaning with every thrust of her hard cock into my ass. Then it hit me like a ton of bricks! I came so hard and so fast I almost didn't have time to think! It was the most intense cum I have ever had! I was literally bucking back against her thrusting into me, crying out over and over as each powerful wave hit me, and my cock wasn't even being touched!! Danni didn't last long either with my excitement adding to hers, she slammed into me and began filling my ass with her hot cum. Still riding my waves of orgasm now with hers, I NEVER felt so amazing in my life! She leaned down and wrapped her arms around me and there we stayed riding out the rest of our unified bliss of post orgasm. After a bit, I felt her begin to soften and slowly slide out of my ass. I turned over to look into Danni's eyes and we kissed again, so lovingly and so passionately.

We showered together then had dinner and some wine, then made love again before falling asleep in each others arms. Yes, I really think I am in love with Danni.
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Old 03-26-2013, 12:26 PM   #14
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Very hot thanks for sharing loved it
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Old 03-26-2013, 04:04 PM   #15
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Wow. Perhaps the story of the after dinner rutting?

Last edited by Metawampe : 03-26-2013 at 04:05 PM. Reason: spelling
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Old 03-26-2013, 06:52 PM   #16
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I talked to Danni on the phone today.....

and "she" told me that she is beginning hormone therapy so she can grow breasts and have more feminine features.... so in a nutshell, he has decided to take more permanent actions to become "she." I couldn't be happier for her and for me. I can't wait to see her again.
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Old 03-26-2013, 09:52 PM   #17
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YOu both sound so well loved up, I am happy for you both

Be warned though, hormone theraphy can cause huge mood swings at the beginning, be prepared for this then your less likely to get upset by it. Hope it works out well for Danni and for you
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Old 03-27-2013, 11:07 AM   #18
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Thank you sweetie!

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Originally Posted by naughtyinsilk View Post
YOu both sound so well loved up, I am happy for you both

Be warned though, hormone theraphy can cause huge mood swings at the beginning, be prepared for this then your less likely to get upset by it. Hope it works out well for Danni and for you
Thank you for your kind thoughts and I will watch out for those mood swings.
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Old 03-27-2013, 11:09 AM   #19
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Jealous!
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Old 04-01-2013, 04:34 PM   #20
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Wonderful!!

I have another date with Danni this weekend.... she wants to help me in my desire to feminize... stay tuned.
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Old 05-30-2013, 05:19 PM   #21
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An update...

Dani and I were never able to get together for my feminizing... she took a job across country and hasn't been able to make it back out yet.... maybe in July she said... so hoping.
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Old 06-04-2013, 05:35 PM   #22
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Very hot stories. Lucky!
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Old 06-04-2013, 06:10 PM   #23
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Afterhours,

Beautiful stories, so pleased for you both , and not ashamed to admit I'm hard too xx
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Old 06-04-2013, 06:36 PM   #24
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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.
Mmmmm....sooo HOT! I'd luv to be in that situation one day. Mmmmm
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Old 06-04-2013, 06:37 PM   #25
getntwoknowme
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Quote:
Originally Posted by Afterhours22 View Post
Dani and I were never able to get together for my feminizing... she took a job across country and hasn't been able to make it back out yet.... maybe in July she said... so hoping.
Hmmm...east coast eh?
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