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An Introduction to Crossdressing Pt 3

"After all the preparation I want it too bad to go out."

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As I was following Jackie to the hotel I couldn’t stop looking in the rear view mirror at what was a complete transformation in my mind. I kept doing that thing where you look away and then back hoping to catch your reflection not keeping up with you because you are sure it is not you. It is probably a good thing that there were not very many cars on the road since I wasn’t paying any attention to it while I was admiring myself.

I did see Jackie’s turn signal and brake lights just in time to make the entrance to the hotel and pulled in to the spot next to him. As we grabbed our things from the car and headed for the hotel I couldn’t help reaching up under Jackie’s dress and fondling his sweet ass. He stopped abruptly dropping his bag, grabbing my ass with one hand and the back of my head with the other and started one of the most sexually charged kisses I have ever experienced. If we were anywhere but the parking lot I wouldn’t have been surprised if we would have dropped to the ground and fucked each other like animals right there.

We held on to each other for a few minutes after the kiss was finished to regain our composure. As I reached down to get our bags I realized that I was quite light-headed from our mutual assault and had to lean on Jackie for a minute before we continued heading to the door.

As we got the the check-in counter Jackie provided the nice young lady with our reservation information. She then asked if we preferred two queen size beds or a king and I jumped right in telling her we definitely wanted a king. I think she understood my exuberance as a big knowing smile broke out on her face. When the check-in girl gave us our room keys and directions she made sure to tell us to have fun and we both turned simultaneously to say we will.

As we entered our room and looked it over I grabbed Jackie and started another of those mind blowing kisses. When we finally came up for air I told him that I was hoping to go out tonight and show off but I couldn’t wait any longer and wanted him to fuck me now. He said that he wanted nothing more than for us to have each other as often as possible in our time together so we fell to the bed and got started.

We tangled up in each other still dressed and started kissing and fondling every inch of each other like two kids doing it for the first time. While kissing deeply I had both of my hands on his ass rubbing and squeezing like I had never seen one before. Jackie had one hand between my ass cheeks with his middle finger in me to the first knuckle gently probing and stretching, while the other hand was pinching and pulling on my nipples. I started to follow his lead and slid one hand between his cheeks and started to ply his sweet ass.

I decided that I couldn’t wait any longer and slowly untangled myself from Jackie just long enough to grab the lube from my bag on the floor and remove my panties. Squeezing some lube onto Jackie’s throbbing cock and then some on his fingers I begged him to fuck me now. He started to slide his fingers into my wanting ass while I pulled my legs back to my chest exposing myself fully for his use. After Jackie had pumped two then three fingers into me about a dozen times my patience escaped me and I demanded that he stick his cock in me now!

Jackie gently removed his fingers from me and moved into position laying his cock head against my entrance and then slid all the way in slowly until I could feel his hips resting on my ass.

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All I can say is it was intoxicating. He then started to pull out a little but I quickly wrapped my legs around his back pulling him all the way in again. I then pulled his face down to mine and we kissed again like there had never been another.

When we finally broke the kiss he started a slow deep penetration and each time he hit bottom he would rotate his hips a few times stretching me open just a little more. I couldn’t resist watching as his cock entered me over and over and I noticed quite a large pool of my own pre-cum forming on my abdomen and filling my belly button.

As I looked back up at Jackie’s face I knew that he was quite close to filling me up so I urged him to pick up the pace. As the real pounding began I saw that tell-tale look on his face of near agony when a powerful orgasm was on its way. He managed a few more strokes before he grunted something about God and filled my ass with spurt after hot spurt. I held him locked tightly inside of me until he was soft enough to slide out and now it was my turn.

Jackie rolled onto his back and pulled his legs apart and told me to take him hard and fast. I reached down and slow slid his panties down his stocking covered legs stroking them as I went. As I reached his feet I gently nibbled on his toes which caused him to flinch a little and laugh, seems he is a little ticklish. I finished pulling his panties off and slowly rubbed both of his legs enjoying the feeling of the smooth stockings.

Jackie finally couldn’t take it any longer and told me to get busy fucking him. I scooped the pre-cum off of my belly and lubed his hole with one, then two fingers. He said that that was enough and I told him that I wouldn’t last long at a hard and fast pace. Jackie said that it didn’t matter since we had all week-end. I slowly eased into him until I was completely in and stopped for a few seconds before I started the pounding.

I drew my cock almost all the way out and slammed back in hard and quickly assumed a jack hammer style. As I predicted it didn’t take more a a few minutes at that pace before I started feeling the beginnings of my own colossal orgasm. I entered him fully one last and held him tightly as I pumped what felt like gallons of cum into his warm tight bowels. Jackie and I slowly slid apart and just laid there breathing for about ten minutes and then he said that we definitely have to do that again.

Jackie got up first heading to the bathroom then turned and asked if I was still interested in going out tonight. I told him that I felt quite happy just staying in to continue our explorations of each other. He said that he thought that was an excellent idea and that we could go out and show off tomorrow night. As Jackie disappeared into the bathroom to clean up I reached into my for my toys and spread them out all over the bed. I heard the shower turn on and headed for the bathroom...

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Written by stockingluvr
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