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Chicago Massage

I was contacted on a massage site about the possibility of doing a massage. He said he wasn't looking for anything more than a massage. I replied back that I was actually free that evening and able to connect with him if we wanted. I asked if he was interested in just a ther*peutic or a sensual one, and if he minded if I was nude during the massage, but I would wear shorts and a t-shirt if he preferred. I also asked if he preferred to be dr*ped or not. He replied that he was fine with me being nude as he preferred to be nude while receiving. He asked that I not use draping because he felt it took away from the massage with having to stop and re-position the draping all the time. He also said he would prefer a sensual massage as long as "all" touching had to do with the massage because he was not looking for a sexual encounter. We set up that I would arrive around 7pm.

When I arrived and he opened the door just wearing a towel as he had just gotten out of the shower. He was about early 40's and very well toned as well as being a very handsome man. He looked at me smiled and said that I was not what he expected. I apologized and said that we could just call it an evening with no hard feelings. He insisted that he was very pleasantly surprised and he really did need a good massage. He then asked if I needed a bottle of water or anything and then led me into his den where he had a massage table set up. He dropped his towel revealing a very nice bubble butt and climbed up on the table. Because we had discussed the massage openly before meeting I knew I could strip, so I undressed. I reached into my bag and got the massage lotion and then started at his feet right foot first. I massaged it and his toes and then moved to the next foot. I tend to do a slow, methodical massage and it takes time. After I completed his feet I moved up his left leg and worked his calves and shins and then moved up to his thigh. As I massaged his thigh my hand went between his legs as I was massaging the inside of the thigh. I bumped into his hard cock that he had pushed back apparently when he laid down. I stayed with the massage and hoped he knew it was an accident running into his cock. I eventually moved up a little more to his glutes. As I would work his left cheek I would occasionally let my hand slide down into the crack of his ass and my little finger would slip past his hole. He started moaning lightly when my hand would slip into his ass crack. Hearing that my cock immediately got hard. I then started giving long strokes across his ass and down his thigh with my hand sliding down his crack each time, when suddenly he reached over with his hand and grabbed my cock. I let him play with it a little before I took his arm and massaged it and his hand. When I laid his arm back down he immediately reached for me again but I moved further up on his lower back and waist essentially moving out of his natural reach. He laid there and just relaxed giving a long deep moan every once in a while. I moved to where I was standing at his head with his face in the face in the cradle on the table. I massaged his head (he had very short brown hair) and neck and then I started massaging his shoulders and upper back. As I started giving long strokes starting at his shoulders and ending at his glutes he raised his head and put my cock in his mouth. I was shocked but continued to give him long strokes more then I usually do because I was enjoying his sucking on my cock. I finally/reluctantly moved off to his right side and worked his lower back and waist and then moved lower to his glutes. When I was massaging his glute I again let my hand slide into his crack and he started to raise into my hand especially as my little finger neared his hole. when I moved down far enough he again reached over and started playing with my cock. I let him play a bit and when I was moving down to massage his thigh, I let my hand slide down and stroke his cock with the back of my fingers and I felt a very wet spot on the sheets as I slid past the head of his cock. I gave him a few long strokes and each time my hand went past the head of his cock the table felt wetter. I moved on down his leg to his foot and asked if he wanted to roll over so I could do the front. Without hesitation he flipped right over revealing a very nice cut cock with pre-cum dripping. I started on his right side shin and moved up to the front of his thigh. I worked it letting my hands rub against his balls with every stroke as I watched his cock to see what reaction there would be if any. His pre-cum was just flowing as he continued to moan lightly. I moved up to below his waist and while gently massaging that area would slide my hand between his cock and his body and let his cock slide across the back of my hand. I then continued to move up higher and massages his pecs and chest under his arms and up across the shoulders. I then worked my way back down his left side and was amazed with how much pre-cum he was oozing. As I was winding down I asked if there was any areas that he wanted me to work a little more. He asked if I could work his shoulders down to his lower back again. He also asked if I could climb up on the table so I could get some good pressure as he wanted me to give a deeper firmer massage. I complied and moved up between his spread legs when he rolled back over. This time his cock was not pushed down (I think it was too hard to push down between his legs again.) As I worked on his lower back and started moving up towards his shoulders when I would go to give a long stroke my cock would slide up against his ass crack. After about the 2nd or 3rd long stroke he raised up against my cock and I almost entered him because we were at just the right position. Having some forethought before I climbed up on the table I had grabbed a condom out of my bag and had it on the table between my knees. After about the 5th time of almost entering him and each time my cock head would slide against his ass hole he would moan loudly and grind up into me. I reached back and grabbed the condom and tore it open put it on. I rubbed lotion on to my cock and when I resumed giving him long strokes again, when my cock reached his hole I could slowly slip the head of my cock in. then I slowly did firm long strokes and would work his ass with my cock pulling out each time on the down stroke. Eventually I pushed deep in his ass. I put my hands up under his upper chest to where I could hold his shoulders. Then when I would slide in balls deep I would pull him towards me so I could get as deep as possible. After slow, deep, fucking about 15 minutes he asked me if I liked using a sling. I said sure. He said "GREAT!!" follow me". So I withdrew and took off the condom and he then led me to what I guess is normally his guest room and hanging from the ceiling was a nice sling. He climbed up in and I adjusted it to the height I needed for best use. He had a lot of toys and lube and a bowl of condoms. I grabbed a condom and some lube then made sure he was well lubed and my cock was too and slid in again for a good long fuck. He came 3 times during our 1 1/2 hour fuck session. After he came the 3rd time he said he was getting a little sore and would I mind if he sucked me for a while. I said that was fine and withdrew. He got up and dropped to his knees, removed the condom and started sucking me off. He was very good and I worked up a load very quickly and I told him I was about to cum he grabbed my ass and pulled me deep into his mouth and I felt my cock plop into his throat. The feel of that I started shooting and he started working my cock again but not before I had unloaded down his throat. He asked me if I wanted to take a shower I said please and he led me to a shower and went and got towels. He entered the shower with me and washed my entire body from head to toe and when he had finished he made sure I was rinsed off and he grabbed a towel and completely dried me. He said my clothes were still in the den so I headed that way to redress while he dried off. He came to the den and slipped on a pair of gym shorts that were laying on a recliner. He told me he had had a great time that was totally unexpected and didn't know when the last time was he had a massage that good that ended with such an intense happy ending. He asked me to please arrange to come back for another massage and asked if I would mind if he had a friend come over also. I told him adding a friend would be very hot but also had to tell him I would if I could, but my daughter was moving and I wasn't sure if I would have time to before I left the area. Anyway, 3 1/2 hours after entering his place I walked out with a grin on my face and a dry ball sack. I unfortunately could not get our schedules to mesh before I had to leave the area.

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