Happy 4th of July!

Then there are days like today.

I always say, never do anything with a client you are not willing to repeat every time you see them from that point on.  That is one of the reasons I never cum for a client (at least on purpose). I have very few clients that I fuck, and when I do, I let them know that this is a one time only thing, it most likely will never happen again, unless we both want it too and either of us can always say “sorry, not today.”

Let’s face it when sex is part of your job, and you are a man, there are going to be limitations. You can only cum so many times a day. You can only keep up an erection for so long. You have to be stimulated to get an erection by something, anything. That is why you should never fuck a first-time client; you are setting up some pretty high expectations. Shouldn’t even get undressed. Leave it at a hand job.

This morning my first client was a great guy who has been seeing me for about 3 years. Things started pretty slow back then: he didn’t try to touch me; I only gave him a hand job when he was very erect. He didn’t say much before or after – just a short embarrassed “thanks.” His wife had left him, he worked two jobs and usually only had one or two entire days off a month. Eventually he started feeling me up outside my shorts and I started giving him prostate massages. One day he takes my shorts off so he can jack me. Another day he pulls my dick out while it is near his head so he can lick it. We slowly over time work up to three fingers in his ass and he seems to really like it. Eventually I ask him if he would like the real thing and he says nothing, so I keep fingering him till he cums. This happens at least twice more before he says he wants the real thing. He is an extremely handsome man, about 50, good shape, huge dick and a very nice ass. We go slow and I fuck him for the first time, he doesn’t last long. I generally pull out as soon as a guy cums, knowing that it can be painful for a lot of guys to still have a dick in their ass after cumming. The second time I fuck him he wants me to keep going – keep stroking his cock and keep fucking his ass after he cums. OK, I can do that. He kept cumming and cumming and grunting and groaning, it was sweet. So that did become the norm, he likes to get fucked, I like fucking him and I ask before we do it and he says yes and so it goes. This morning was no exception except that we had not seen each other in months due to his schedule before the lockdown and then the lockdown itself so the passion of the moment was a bit higher than normal and a good time was had by all, keeping in mind that I don’t cum.

Ninety minutes later I greet a new client at the door, Randy. He is about 30 years old, 6’, shaved head, well built and very friendly. We are both wearing masks due to Covid. He wanted to know if he could shower before hand and I showed him to the bathroom with a towel and wash cloth. After his shower he returns wrapped in a towel and wearing his mask. He drops the towel and stands naked except for the mask and says “strange world we live in, where do you want me?” I tell him to lie facedown and offer a towel for draping to which he replies “I’m not shy.” He is hairy and well hung, has a multitude of tattoos – mostly Celtic in design in black and bright green. He has a prince albert piercing. I ask the usual about whether he has any aches, pains, illnesses or anything I should know about. He tells me he in the army so he works his body hard, but especially he legs and glutes as of late. I go to work and he is friendly and chatty, compliments my home, pride flag, choice of music etc. I tell him to let me know if I ever use too much or not enough pressure, he likes the deep pressure. I have an erection through most of the massage. He is flirty, nice, attractive and behaving like a gentleman – perfect. I remind myself that I am 20 years older than him and in not nearly as good of shape. It is not until I do the abductor rub under his leg that he first finds my erection and starts rubbing it. He is very receptive as I rub his glutes and when I narrow in on his sphincter, he lifts his hips only very slightly. I ask him it he would like a prostate massage. “Sure, why not?” I start with my thumb, then two fingers, then three… driving them in and out and finally 4 fingers slide in.  So… he is not a virgin.

I ask him to turn over and work immediately on his abs, sliding down over his pubic bone. His cock is erect and I work it lightly then down to his balls. He is freely rubbing my cock through the shorts, so I finally drop them. I switch sides of the table and repeat and then linger with one hand massaging his sphincter and the other working his nips. I couldn’t help myself; I ask if he would like to be fucked. “Why not?” I tell him that I don’t usually do this especially with a new client, but it is the 4^th of July wknd and he is active duty. I put a condom on and throw his legs up over my shoulders and ease in. He is staring intently over the mask into my eyes, as I am staring at his. This is unusual. Most guys will look at me then away, then roll their heads, back at me, close their eyes etc. He has locked eyes with me and not letting go. OK, I can go with that. I fuck him hard and intense, keeping my eyes locked on his, jacking his big cock (careful of the prince albert). I feel he is close but his eyes are looking at me without flinching. I nod my head. He says “here it comes, I shoot a lot!” He puts a hand up to shield his face as volleys of cum fly over his head, on his hand, shoulders, chest and eventually stomach. I laugh as I clean him up, he is extremely sensitive after. I finish the massage with stretching and some deep tissue on his legs and arms. While I work, his hands find my legs, ass, cock, whatever naked body part is closest to him.

When it is over, he gets dressed and repeatedly tells me how good it all was and that he will definitely see me again. He leaves me a nice tip and I show him to the door. In the pre-covid time, I would have hugged him and possibly kissed, but today it is a nod and a “hope to see you again soon.”

Afterwards, I realize I have broken a few rules, but I still haven’t cum and I am still good for another massage or two. So far, a good day.

My story of Tom AKA Andy

I first saw him in October of 2006. He had found me on Craigslist and then on an online massage exchange group that I helped run and sent me an email and introduced himself as Tom. When he showed up at my door for his first appointment what struck me were his wiry unkept hair, his dark frame glasses and how thin he was. He was incredibly nervous. He told me he had not done a lot of this sort of thing and that he was married to a woman and that he was in his 50’s. He was also a diabetic with an implanted insulin pump. When the appointment was over, I noted in my log: Thin, nervous, married, no prostate massage, sensitive balls. I had remained clothed for our first session. The last time he saw me for a massage was October 1, 2014. He saw me 70 times in those 8 years, 90 minutes almost every time. It took him two years to tell me that Tom was his first name but he went by Andy, his middle name. He only used Tom when trying to hide his identity on line.

I took my clothes off for him on our third session, his request. We would spend some time of each session just talking. I heard about his marriage, his kids and his jobs. We talked about whether he should tell his wife about his sexual and emotional attraction to men. I pointed out that as long as he didn’t, he was not allowing her to deal with it, one way or the other. He eventually did tell her. They eventually split.

One day he asked to explore my body, so I lay on the table and he gave me a massage. He wasn’t very good, no reason why he should have been. He claimed I was the first cock that he put his mouth, I believed him. Eventually he got over his fear of anal and asked for a prostate massage. Over time we worked up to three fingers. He eventually wanted to be fucked, and after much discussion, I agreed to take his ‘virginity.’ It would be something that he would ask for occasionally after that. His favorite activity though was always frottage. He liked sucking cock as well, but he preferred when I climbed on the table and we rubbed our bodies together until he came. He also had an underwear fetish and loved modeling his latest purchases, and occasionally would bring me a pair to keep.

There was a six month break in seeing each other. When he returned, he explained that he had been seeing someone else and didn’t want to cheat on him. I said I understood, though he was still living with his wife at the time so I was confused. After that session we talked about the relationship that he had just finished. Turned out that it was all on line. They would chat, send pics and jack off together on video. However, when Andy wanted to meet, the other guy ghosted him. Andy went through the angst that many older people feel when they start coming out – they are too old to fit into the gay world, they waited too long to come out, they missed the best days of their lives. I offered him many suggestions of where to go to meet men that he may be interested in and may be interested in him. There was another break when he felt that he was becoming too emotionally attached to me, even though we only saw each other once a month at most.

It was a few years between when he told his wife and when he told his kids, and then only because he had decided to move out and get his own place. Their reactions were mixed, somewhat supportive and they loved him, but an over whelming sympathy for their mother for being lied to (as they felt they were lied to as well).

He moved to the far side of the city and he stopped seeing me as a client. He called occasionally and sent an occasional email. I saw him out at the bars a few times. He was more comfortable with himself than I had ever seen him. He was genuinely happy. To the best of my knowledge he never found a full time male lover, but he found friends and he found sex partners. He came out loud and proud. He marched in gay pride parades. He wrote articles of gay men in art and in history! He became a leader.

I heard he passed away in May. He was 66. I don’t know what he passed away from, doesn’t matter. It was a life well lived.   

- Jack