A little background about me, I am a married (bi) chub who only plays around when traveling for work. I am 46 years old, clean shaven, brown hair, mwm, blueish eyes, 5'11" tall, 366 lbs, with a 6 inch cut (small girth) cock. I am smooth chested with only pubic hairs. I have a nice set of big balls though.
As I travel I usually check out craigslist and try to schedule a massage while I am there. The company I work for is located in Alabama and my position has me traveling at least 3 times a year to conventions or workshops.
There are many stories I could tell you about different massages I have had in different cities (actually only about 7 massages over the last 12 years) so you will know this one was definitely the best I have ever had.
First off, I traveled to New Orleans for this trip. I had scheduled a massage for the first night there, the man came to the room, it was good, just your run of the mill more of a back and body rub with a happy ending.
After 2 days of sitting in meetings and was tired as all get out, I went downstairs to have the concierge to make reservations at a fancy restaurant for that evening and I commented that after dinner I needed a good old relaxing massage and wished I could have one late after my colleagues and I got back from dinner, and then I said but that is impossible that late at night. After the concierge made the reservations and told me some of the entrees they are famous for, he said, I have a male masseuse who makes late night hotel visits if you are interested. I laughed and said oh yes I am interested but I doubt they can come that late. He said give me your cell and I will text you if he can come. I tipped him for making my dinner reservation and thanked him and said, I hope I get a text laughingly.
Sure enough I got a text about 10 minutes later asking would 11:00 p.m. be ok for the massage and would that give me enough time to get back to the room, shower and be ready for the massage of a lifetime. I said it would because we would not be going to a bar because the next morning would be an early one for all of us. At dinner, I kept on thinking about the massage. I wondered if it was going to be a straight massage or possible erotic. When they are set up by hotel staff, you never know and since this was a high end convention type hotel, I just assumed it would be a regular massage.
After dinner, I got to the room, I straightened up the room, put away all of my work papers and books and then I took a shower. It was about 10:45 and I was really getting excited. I was wearing a polo with a pair of shorts and I had on my boxer briefs. At 10:59 sure enough, a knock at the door, I went to the door looked and a man in a suit with a brief case was standing there. Confused, I opened the door and he said Mr. Sullivan, I think you are expecting me, I am Jeffery Jackson, a licensed therapist, but everyone calls me Jeff. I invited him in. He came into the room and asked if he could hang his suit in the closet. I decided to make small talk and I told him I was shocked to see him arrive in a suit.
He then explained, he said when traveling to a convention hotel, especially those arranged by the concierge he makes sure there is no stigma related to him showing up to a clients room. I am already very impressed. First off, his looks in the suit. He was a very dark tanned olive skin man. Very handsome, short brown hair and with a very trimmed 5 oclock shadow. Just that sexy face you want to make out with. He was about 5'10 and I bet he weighed about 180 lbs. when you looked at him in the suit. The suit was a perfect fit for him, he looked like a person who would have been at the conference with us all week.
When he took off of his suit, he had on a pair of boxers and t-shirt. He looked very sexy with that tanned, and now I could see muscled body. He then explained the way he does his massages. He gives the man a choice, he can do it in a pair of shorts, in his boxers, or in the nude. He said that it would be best if I was in the nude, but if I was uncomfortable he could drape me with a towel or I could wear underwear. I then stopped him and said look, I want a real massage because I know you are licensed and will give a good true massage, but at the end, I would love to have an erotic massage. The concierge had told me in the text that the cost is $ 200.00 and it was for 2 hours of the masseurs time. The therapist said let me explain the ground rules, my charge for the time here is $ 200.00 and what we do in that time is strictly up to both of us. He said since I had expressed an interest in an erotic massage that he would do the first hour as a real massage just like you would get at a salon in town, and then after he starts touching we are both welcome to explore. Well my 6 inches were busting now to get out of my shorts and we had not even gotten started. He said, why don't you get two towels from the bathroom and lay them on the bedspread and then lay face down across the bed. Once I had brought the towels out he placed them on the bed, I stripped down and laid across the bed on the towels. He excused himself and went to the bathroom and came back in the room and turned the tv to a channel that just had music in the background. It was all instrumental jazz. He was nude and I had to look. Oh my goodness, the perfect chiseled man, very nice muscle tone with a solid 6 pack. His complexion was a perfect tan all over. We did not do much small talk after that, he would ask if the massage was too deep on my back, it if felt ok, etc. You could feel the tension releasing out of my back. He paid special attention to my neck shoulders arms and back, then went to my lower extremities. Wow, he stretched my calf muscle after he ran his hands across them one time. He said they were way too tight and needed to be relaxed and stretched. I must confess this massage was the best I have ever had and we had done nothing sexual at all. Finally after a good 15 minutes on each leg he went up to my hamstring, thighs and glutes. So professional. Next he asked me to turn over and when I did he saw my raging, he ignored it, because of my huge stomach he only did a rub, but on my pecs and shoulders he did a nice relaxing massage. Next he massaged my legs and his touch on my feet was electric. By now as you can imagine, a little over an hour has passed and my raging hardon was flying everywhere. I was scared when he touched me finally in an erotic way I would blow right there. It was two days previous that I had the happy ending so I had not shot a load since.
He next came up next to my head and he leaned down and licked the side of my face with his tongue and whispered in my ear, are you ready for the time of your life. I just turned my face towards his and stuck out my tongue and we kissed and long passionate makeout style kiss. I was in sensory overload. I told him I had a major problem and that the first time he touches me I am going to blow and when I blow I blow lots of cum and it shoots everywhere. He said that he normally likes to take things a different direction but since I was honest up front he whispered I have a surprise for you. He went down and put his mouth over my cock and sure enough, I erupted and he went to the base and just gulped and gulped and gulped. Finally when I started to come down from the excitement, he went up by my ear kissed it and said let me run to the bathroom, you relax and I will be back, he went, I heard him wash his mouth out and then I heard him piss and flush and in a flash he was back laying beside me and we continued to make out for a few minutes. He had obviously washed his mouth out with mouthwash because it was all minty and refreshing when we kissed. I remembered my scope was on the counter. He again whispered for me to turn over on my stomach and now the erotic massage would start and boy was he ever right. He moved my legs over wider so that he was kneeling in between my legs and leaning over me massaging my shoulders, slowly moving down my back. Then I felt it pressing my leg, his cock was poking at my leg, it felt big in length and girth. I had laid my hands by my side hoping that I might could feel it next time I get the opportunity to cop a feel. I was still enjoying it so much. He leaned back on me his chest on my back and he asked me in my ear, he said with you being married, I need to know if you want penetration. I did not respond, he said that he would be happy to use tongue, fingers, cock with condom or without condom, just how ever I wanted. My response was tongue and finger would be all that I was interested in. He said that is fine, so now his rubbing of a different type of oil than the lotion he had used earlier, he paid special attention to my buttocks and inner thighs, next he slid my cock down towards my feet where it felt like it was hanging below my balls pressed against the mattress with just the head and a little more sticking out getting air. His caress of my balls was again making me raging as hard as I was earlier. He ran his fingers down the crack of my ass and then he spread open my cheeks. Then I felt something warm and then I felt it, his tongue was going deep inside, now I am going crazy moaning. He laughed and said you have never been treated right, he said for me to let him know when I was ready to cum again because we were no where close to finishing the experience and he wanted me to save one last load for the finale. My mind was going crazy. I had just been rimmed by the best tongue ever. Little did I know but the rimming had just started. I was doing nothing but moaning to the point of almost disturbing people in the adjoining rooms. All he could do was giggle as his tongue kept working. Next was the attention he was paying to my balls, by this time I am up on my knees with my ass high and balls and dick hanging. He goes back and forth with his tongue up and down my crack between my balls and my hole and I am by now moving with my face in my pillow almost yelling. I said one time, I am going to blow again and he laid me on my back and took my cock in his mouth and this time I was able to enjoy a minute or two of the blow job before I blew again down the back of his throat.
He again kept sucking until I had calmed down, but I was so sensitive that even the touch of his tongue had me twitching. He giggled and would touch it again on the tip and head. After about two or three minutes he excused himself and went and washed out his mouth and I could hear him use the scope and spit out and this time he did not piss. He came back in the room and we made out again. He asked me if I had ever had that done, I confessed that only twice before had I ever been rimmed but that was by far the only real rim job I had ever had. He laughed and asked if I was up for a little more play. I said yes, so we made out some more and somehow I was back with my ass up in the air and he went back at it. This time almost assaulting with his tongue. He was doing smooth licking strokes but attacking my hole and going nose deep in my anal area. This was driving me crazy too, again he went down to my balls sucking on them and massaging them playing around and then I felt his finger, wow, it went deeper and deeper, and without thinking I said hell is that your elbow in my ass, he busted out laughing. It almost made him stop for a second and then he continued on with his tongue and fingers and then the tip of his finger was a deep as it could go and he twisted it in my hole and boom, like that a bolt of lightning hit me like I was shooting stars everywhere, when he hit that spot my hole closed and almost cut the circulation off of his finger and he immediately stuck my cock down his throat. I was moving about everywhere all over the bed screaming in the pillow. It was a feeling that I have never had before and this time I had a dry cum. He came back up and kissed me and held me and we just cuddled beside each other. We stayed like this for about 5 minutes and I now realize he was trying to let my body adjust to what had just happened. After we cuddled for a while, I wanted to continue so I started kissing his neck and that was all the sign he needed and then we were back at it making out again. I was brave this time and I started playing with his cock which was semi hard. It had gone down from the hard state it was in earlier. When I started playing with it and rubbing it, I could feel it harden back up in my hand. I was jacking him and by this time we got in a 69 position and he was very slow during my blow job. He was so gentle and took me all the way back in his mouth going up and down. All I was doing was playing with his cock and gently sucking on the head and licking the shaft and balls. But to be honest, I am not a cock sucker so it was not enjoyable for me to try to get that big thing in my mouth. Now playing with my hands and licking was wonderful and had a great time doing it but I just could not bring my self to suck more than the head. (to his defense, he never once asked me to do it and he never mentioned it, when I would lick or suck the head he would moan in approval). This time he was gentle and then started to really go to town on my cock. He looked up at me and asked if I had ever topped someone before. I told him that I had only done it once in college and once on a trip to Miami about 10 years earlier. He laughed and said well we are going to let you have a good time tonight. He got up went and got some things out of his briefcase and he slid and condom on my cock, he kept playing with it sucking it and keeping it rock hard. He said "since you have already cum twice and dry came once, I probably don't need this condom, but we always need to be safe." I agreed and told him that I would need his help to achieve this. That the one 10 years ago in Miami was another chub and we had to get in perfect position for me to get inside him. He assured me not to worry, that he wanted my manhood inside him and he would find a way. Well after he used his fingers to oil up his hole, then he told me to use my fingers to loosen him up and I oiled my fingers and played around all the while he was making sure my cock was still hard as a rock. He told me to put a pillow under my ass which we did, he next stood above me and slowly bent down and then he guided me inside his ass. Oh my lands, this was another complete sensory overload. I was out of my mind. It was tight, it was warm it was smooth and then he slowly started to ride up and down. I started to get a rhythm and literally in about 5 minutes I was moving my hips up and down bouncing the bed as much as I could. This feeling was also unreal. After about 2 more minutes he slowly started to pull up and my dick popped out like a thump and he said get up, I want you to fuck me doggie style. He got on all fours and I was on my knees and believe it or not, my belly did not get in the way. I was really able to go to town at my pace now. I started to fuck as hard as I possibly could and I started to moan and grown and stiffen up and he quickly pulled off of me turned his head around and yanked the condom off and sucked all the way down to where his nose was buried in my pubic hair and his throat was massaging my head. I was again blowing another load. This time it was only one spurt and some dry cum, but the feeling was still there and I was again letting the stars swim around my head. I had to lay down, he laughed and he laid down there with me, caressed me and kissed me slowly. We neither said a word just pecks on the cheek and a passionate kiss every few seconds.
I glanced past him and looked at the clock and I said Jeff, man I am sorry, I have kept you past your time. It was 1:48. That time will be etched in my brain. He looked at me and said that he was only being paid for the first hour, anything that happened after that was because he wanted to be here with me.
For the next 45 minutes we talked, he told me about how I reminded him of his high school football coach. After graduation his coach also had a farm and players would help him in the hay field etc each year. During the week of the fourth of July his wife and their kids and all the other player/workers had gone to the beach on vacation. I could not go so I stayed there and worked. I got over time after we had worked 40 hours that week so everything from Thursday noon was 15 dollars an hour. That Thursday night we had worked until dark and it was late, he said why don't you call your mom and tell her you are staying here and then we can start work at 6:30 in the morning, so that night we were watching TV and he went and took a shower came back in the living room with nothing on but his boxers so I went and took a shower and did the same, we ate a sandwich for supper and to be honest, he said that he started looking at his coach and just started to lust after him. He said the coach never made a move or anything, but just being around him he said he felt the urge that he was attracted to men. Nothing happened, just the next day he found another reason to stay over and he tried to watch the coach everytime he went to the bathroom etc. He said the coach was a little over weight but that I reminded him of his first love even though they never did any thing sexual that he could visualize me being his coach and he wanted to do everything he could to please me. I asked about the suit and what he did for real. He said that he came to New Orleans that fall and went to Tulane. He has a degree in management. He was hired by one of the oil companies and to this day he is working by day in the big office building. He said he has befriended 5 or 6 of the male concierges at the popular convention hotels and they funnel him leads. He gives them a 20.00 referral fee so they keep him busy. He tries to only do one or two massages each night and he can do as many as 4 on Saturday or Sundays. He gives the male concierges a freebie to start off. He said when you do it slow and ask the client what they want to do, you have pretty good experiences. After talking and cuddling for about 20 more minutes he said I don't have to be at work till 9 and since I already have my suit here and a change of clothes in my brief case, he said can I just stay the night. I agreed. I said now I get up at 6 since my first function at the convention is breakfast at 8. We got up at 6, took a shower together, he gave me one final blowjob for a good measure. He shaved and I just watched, he trimmed so that he still had the 5 oclock shadow when he headed out the door. We kissed one more time. I gave him his $ 200.00 and then I got my wallet and pulled out another $ 100.00 bill and told him I wished I had more because he was definitely worth it. He looked at me sincerely and said no, only the original 200 but I made him take it. I know the rent in New Orleans is expensive. After a little more small talk he said now if you ever get down here without your wife and kids and if you do come with them but get away, he wants to get together for us to have fun. He jokingly said that since he went to Tulane, he is not really an LSU fan because his home was in Iowa, so he said his SEC team may now be Bama. On the way out the door he kissed me again, we went to the elevator together, I got off on the 2nd floor for the conference and he went on down to the first floor. Sitting in the luncheon, I get a text, Jeff said hey what you doing tonight, you want to go to dinner. Of course I made up an excuse as to why I could not go with my fellow workers so Jeff and I met for dinner at Commander's Palace. After the meal, I looked at him and said what is your schedule tonight and he looked at me in the eye and said I hope I am going back to your room for a nightcap. Sure enough around 9 the door closed behind us in my room. He said do you mind if we just forgo the massage and just go to bed.