tagTranssexuals & CrossdressersHis Ultimate Fantasy

His Ultimate Fantasy

byC2RJ©

Jeff and I had been back together for a little over 5 years when I had decided to give him his ultimate fantasy. To everyone who meets him, Jeff is the all American boy. He is the quintessential small town boy. He always has impeccable manners, says his "ma'am's" and "thank you's" in all the appropriate places. However, I knew there was something bubbling underneath that calm, cool, collected exterior. I also knew that when we were dating many years ago, I had unintentionally turned him on to the kinkier side of sex. I had a huge collection of porn I had gently taken from an ex when we split. It had every genre of porn you could think of. As a joke, I had shown it to him and told him to pick what interested him. Little did I know what I would start by that suggestion? Fast forward 15 years and we are to today. My sweet Jeff is a hard working man, always does the right thing, and looks out for everyone else, so I was going to do something for him that he didn't expect and NEVER would ask for himself.

The evening started out a little different than Jeff expected. I called him from work and asked him to meet me at a local favorite restaurant. We are the sick, lovey-dovey couple that is sitting beside each other at a restaurant, holding hands, and flirting with each other, rather than sitting across from each other reading the newspaper. I've done many naughty things to Jeff under the table at restaurants around town, but those are many other stories to come! Previously in the day, I had contacted the restaurant and asked if they would help me out with a surprise for my boyfriend, kind of like putting the engagement ring in a drink or roll. The manager said they could help me, so I went by the restaurant early and left my surprise for Jeff. When dinner was over and it was dessert time, the waiter brought an envelope instead of the menu. He handed it to Jeff and said, "Your dessert is in this envelop, compliments of the lovely young lady on your right."

Jeff turned and looked at me. "What's going on sweetie?" he said.

"Open your dessert and see." I coyly said.

Inside the envelope there was a picture of a very beautiful woman. Her name is Dawne. She is a 6 foot tall, redheaded goddess with a beautifully voluptuous body. Her breasts were perfect at a 36 D, high and perky. She has full pouty lips that remind you of a porn star. She had blue dreamy eyes and long silky hair that begs to have fingers run through it. Jeff's eyes lit up. He had always wanted a threesome but never would ask for one. He thought I was going to give him one now, but I had a bigger surprise for him! On the back of the picture was an address of a very nice hotel.

I just smiled at him and said, "Are you ready for dessert?"

We left the restaurant in his truck, and held hands all the way to the hotel. I had the key to the room already so we went straight to the door. At the door, I paused, looked at my sweet Jeff, and kissed him. I walked in the door first, followed by Jeff. He had his hand on my low back, like always, and he was trembling.

Dawne was in a royal blue low cut dress and was laying on the bed waiting for us. She smiled at us. I walked over to her, climbed on the bed, and kissed her. Jeff stood there watching us kiss each other. There was a chair in the room, put there by my request, so he sat down. He enjoyed watching Dawne and I kissing and it showed clearly by his cock growing hard in his slacks. I got up on my knees on the bed facing Jeff in the chair. Dawne ran her hands over my body from behind. I had on a yellow button down blouse and a loose fitting skirt. Dawne slowly undressed me in front of Jeff unbuttoning the blouse buttons first. She pulled the blouse apart to reveal my breasts in a new bra Jeff had not seen before. Jeff moaned his appreciation of the new bra and how Dawne was running soft feminine fingers up and down my stomach and breasts.

Dawne pulled my blouse off my arms and threw the blouse at Jeff in the chair. He caught it and brought it to his face, smelling it and feeling the soft texture against his skin. Dawne undid the front clasp of my bra and let my breasts pop free of the material. She grabbed my breasts in her hands and played with them as she kissed my neck from behind. Dawne's fingers travelled down my stomach to the hem of my skirt and gently pulled the skirt up. Jeff got to see first that I wasn't wearing any panties before Dawne's fingers found my skin. Dawne and Jeff moaned at the same time. Jeff's eyes were looking directly at mine when Dawne's fingers went inside me. I gasped at the absolute silkiness of her fingers against my pussy. She put her fingers in me and

brought them out. Dawne then put her fingers up and beckoned for Jeff to join us on the bed.

He moved from the chair at an alarming speed for a man who is 6'6" tall. Jeff eased on the bed just under me and began licking my pussy. His arm snaked under me and ran up Dawne's leg. The simple feel of his tongue on my pussy lips was enough for me to reach my first orgasm. I had been thinking of this all day and to finally have him beneath me licking my pussy, with Dawne behind me rubbing my breasts and kissing me was all I needed. When I came, I leaned forward to lay on top of Jeff's body. He still had his clothing on and the texture of it against my skin made my orgasm even more intense. When I was finally done convulsing, I moved forward on his body and turned around. I was laying on his body facing him. He was looking between me and Dawne, wondering what to do next.

I leaned down to kiss him deeply, knowing that both he and I loved the taste of me on his lips after he had gone down on me, and whispered in his ear, "She's all yours!"

"Really?" he said.

"Yes! She is your dessert. My dessert is watching you and a little playing!" I said.

Jeff is a shy man so I knew that he would need a little prodding. I sat up on Jeff and beckoned Dawne to move closer to the both of us. I kissed her again and then she kissed Jeff. I was sitting with his hard cock pressed against my pussy and the instant Dawne kissed him, his cock jumped. He was looking at me to make sure I was okay with this.

"I am so okay with this, if you are, my love." I said.

I scooted backwards on his body and walked backwards to the chair. I wanted to watch him have fun with her. Jeff scooted back on the bed so his back was up against the headboard. Dawne straddled his lap and started kissing him.

"Put your hands on her hips, sweetie." I said.

Jeff moaned and put his hands on her hips. Dawne started rubbing against Jeff's cock through his slacks. He moaned again. Dawne leaned back and started to unbutton his shirt. She ran her fingers over his chest while she ground her hips against his cock. His head fell back and he reached up to run his hands over her arms. He was enjoying this immensely! At that moment he looked up to make sure again that I was okay with what was happening.

"Go ahead sweetie. I love the show!" I said as I sat completely naked on the chair.

He smiled at me with all the love in his eyes and lost his apprehension. He reached up and began playing with Dawne breasts through her dress. He sat up and kissed her chest, neck, and lips. He reached behind her to unzip her dress. The dress fell to her waist and she didn't have a bra on. Her beautifully perfect tits were right there in his face. He took one breast in his huge hands and kissed her little nipples. He sucked one in his mouth and worked his magic on her nipple. Jeff can do wonderfully erotic things with his tongue and mouth. He has a technique that even I, after being with him for five years, cannot figure out what he does with his tongue. However, I can tell you that it feels so good that I feel it all the way to my pussy. The way he pulls my nipple into his mouth and lavishes it with love, attention, and pressure from his mouth, shows me how much he wants to bury his cock in my pussy. I knew that Dawne was getting the same treatment on her nipples by the way she was moaning.

Dawne decided she wanted to move things along. She pulled back from him and moved back on his lap. Jeff is 6'6" so he has a very long lap. She moved back and unzipped his slacks. With some quick movements he was naked on the bed with this gorgeous woman sitting on his lap with her dress at her waist. I had told her how big his cock was and she wanted to see it for herself. He never disappoints!

Jeff has the single most beautiful cock I have ever had the pleasure of having! At the base of his cock he is at least 7 inches in girth and as it goes up the entire length of 8 inches, his cock gets slightly smaller in girth, however, the tip is still a good 5 inches in girth. The head of his cock is a nice big mushroom head, wonderfully smooth skin and a large vein running down the underside of it. I love having that cock inside my mouth and was very descriptive of what he likes to Dawne. She was salivating looking at his cock. She bent down and took him in her mouth. She went to town on his cock and he was looking at me the whole time. He was enjoying what she was doing, but I could see it in his eyes that she was in no way close to as good as I was. I cocked my eyebrow to this and he shook his head. He was telling me that definitely I was so much better at taking his cock than she was, but he did like what she was doing.

She knew she wasn't going to get him to cum, so she leaned back and started getting undressed. Now is when he was going to see that his dessert is in fact, his ultimate fantasy! Dawne peeled her dress down her voluptuous hips and let it fall to the floor. She bent over and pulled down her pretty yellow panties. Her outfit was out of respect for me as it is my favorite color combination. As her panties fell down, Jeff saw that Dawne was a shemale. She was in fact a male with breasts.

Jeff looked at me and said, "Oh my Lord, thank you my love. You are the most wonderful woman ever!"

Ever since that day many years ago when he pulled the porn out of the box I offered him, he had had a fascination and secret desire to have sex with a shemale. He has secretly fantasized about being with a man who had breasts and acted like a woman. Dawne was very tall at 6' but she had a relatively small cock. She had a skinny cock that was only about 5 inches long erect, exactly what Jeff needed to experience his first anal experience (another fantasy of his). But first, he wanted to practice the cock sucking techniques I have talked about for years. He beckoned Dawne to the bed with his finger and she lay down. Her creamy long body and legs spread across the bed with Jeff's long body over her was a sight to see from my vantage point. I was definitely enjoying this dessert and because of the earlier pussy licking I had received, I was dripping on the chair.

Jeff started stroking her cock up and down with his big hands. He leaned down and licked her cock from bottom to top and ringing the head with his tongue. Ever so slowly Jeff put his lips on Dawne's cock and slowly took each inch of those 5 inches in this mouth. His big hand came up and gently grabbed a hold of her balls and played with them, as his mouth moved up and down that little cock. By the way Dawne was moaning and crying out, Jeff was better at sucking cock than Dawne was. Jeff was doing a really great job on Dawn but Dawne didn't want to cum in Jeff's mouth. Dawne wanted to cum in Jeff's ass. You see this was not the first time Dawne had been with a man. She enjoyed being the first one to enter a man's ass and she knew that Jeff had never done this before.

Dawne stopped Jeff and said, "I want your ass big man!"

Jeff was a little apprehensive about this but I encouraged him on. Jeff stayed on all fours facing me and Dawne started touching Jeff's ass. Dawne took her time getting Jeff used to being touched and grabbed the lube on the table. Dawne put some lube on her cock and then on Jeff's asshole. She slowly circled his hole with her cock and gently inched the head into Jeff's ass. Dawne stopped as soon as her head went in and Jeff was panting from the intense surge of pleasure and slight prick of pain as Dawne's cock inched into his ass. After some minutes, Dawne finally was balls deep in Jeff's ass. At this point, I knew I wanted in on this action as well. I got up from the chair and slid under Jeff. He had a lot of precum on his cock and I was so incredibly wet, that I had no problem sliding his cock inside my pussy with Dawne in his ass. Jeff looked at me in the eyes as I did this and his eyes were glazed over with pleasure.

I smiled at him and inched his cock further into my pussy. At the same moment that Jeff was balls deep in me, Dawne started moving in and out Jeff's ass. Jeff just about exploded then. I kissed him longingly and lovingly as Dawne increased her speed. Dawne and Jeff were close to cumming. I broke the kiss to ask the question Dawne needed to know.

"Do you want her to cum in your ass honey?" I asked.

"Please!" he gritted out between his teeth.

I shook my head and Dawne came at that second. She came deep inside Jeff and at that moment, Jeff also came inside me. Long, panting, gasps escaped all of our lips. The biggest load I had felt in a very long time shot out of Jeff's cock.

Jeff fell exhausted to the side of me and Dawne fell exhausted and spent on top of Jeff. Ever so slowly Dawne inched out of Jeff's ass. They lay panting on the bed and I got up to get some wet wash cloths from the bathroom to clean them up. When I got back to the main room, they had separated and were laying on the bed looking at each other. I climbed onto the bed between them. I lovingly cleaned Jeff off, kissing him as I cleaned him. I then turned to Dawne and cleaned her off as well, also kissing her as I cleaned. They both put a hand up and each one caressed my breasts. I could see absolute love in Jeff's eyes.

"Now it's your turn my love to have another first. You get to have Dawne's ass while I watch!" I said.

Dawne was more than ready and got on her knees. She also was not new to receiving from a man who was very well endowed. I put the lube on Jeff's cock stroking him with my hand to get him completely hard. I then put lube on Dawne's ass. Jeff eased closer to Dawne's ass and I leaned over to kiss him. As he slipped effortlessly into Dawne's ass, we kissed deeply. He was looking at me with so much love and adoration; I knew that this was the perfect dessert for him. As he pounded away in Dawne's ass, he watched me watch him. Jeff grabbed a hold of Dawne's hips and buried his cock all the way in her. She gasped and threw her head back, arching her back.

This was when I finally saw Jeff lose complete control. He reared back, let out a groan so wonderfully sexy that I felt it. One of his large hands went up to her long red hair and grabbed a hold of it. He wound his hand in her hair and pulled back on it. His other hand was on her shoulder pulling her towards his cock. He pounded inside her like an animal. No restraint. No manners. No care. He dominated her. I saw an animal in my sweet Jeff. This is what I saw inside of him and this is what I wanted to unleash. Dawne was screaming in pleasure as Jeff rode her hard. Dawne came in long streams of cum. As she came, her ass gripped Jeff so tight that he came. He leaned back, straining, and screamed out as he came over and over inside her. It was the single sexiest act I had ever witnessed. My sweet, calm, collected, well-mannered, polite lover turned into a wild animal who dominated this woman. I came as well, with no penetration and no touching. From simply seeing this beautiful act, I came.

As we all laid there on that big king bed, panting and riding the waves of our own orgasms, Jeff looked at me and said, "Thank you for believing in me and giving me that last chance. I love you so much. You have given me everything I've ever wanted."

Soon after Dawne got up and went to the bathroom to clean up. Jeff and I lay in the bed, in each other's arms. Dawne quietly left after cleaning up. Jeff and I spent the rest of the night holding each other. The best dessert ever, swimming in our heads.

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