Trying Out a Role Play

I had just checked into my hotel room in Phoenix after a long day and a flight in from the east coast. When changing planes in Dallas, I had gone to the short-term executive office suite operation in the terminal, logged onto Craigslist and posted an ad in the man for man personals in Phoenix indicating that I'd be there that night and would be interested in some safe play.

Upon arriving in my hotel room, I logged onto my email and found about 20 responses to my post. The great majority didn't appeal as some were one-line statements to the effect of, "Let's do it!", "I want to suck you dry" or some other meaningless statement that made me certain I did not want to even reply to the message. Others were indicating that the guy wanted to do a whole lot more than the safe play I had described. Deleting those as soon as I saw them, I went on to the remaining ones that held some promise and found one from Jim.

Jim described himself as a 31-year-old bi white guy who lived in the Phoenix area and said he was seeking a role play with an older guy. He indicated that he only wanted safe play and that he had a girlfriend who he had good sex with and that she didn't have any idea that he had a desire to experience something sexual with a guy. He said he had wanted to explore some guy-to-guy fun for quite a while so long as it would be all safe and not pose a risk. My cock immediately twitched as I thought it sounded promising.

Jim said he was a guy-next-door type of guy, about 6 feet tall, clean cut, trim build, in good shape from sports, smooth body, no facial hair, with a 6" cut cock and shaved balls. Attached to the message was a naked photo of him standing with his back to the camera that was shot in a bathroom mirror reflection. He was indeed in good shape, smooth, slender and looked very attractive to me. I emailed back to him with a few pictures of myself saying that I was interested and could host in my hotel room.

As the night went on, I did not hear anything further from Jim and I assumed that maybe what he saw in my pictures didn't interest him or that he had just changed his mind. That was a bit disappointing but OK with me because I believe this kind of play needs to be a situation where both guys are into what they see and what each other wants to do. Nothing else appealed in the responses that night so I used the turn on I got from looking through Craigslist at other posts and pictures as something to help me get myself off before I went to bed.

The next day I checked my email and found that Jim had replied to me earlier that morning. He said that his computer had gone down after he replied to my post and he didn't see my email until he was able to log back into his special account. He was very sorry he had not seen my response because he would have definitely wanted to get together and wondered if I might be in town that night. I replied saying I was heading out of town that day and only there the one night but that I thought I'd be back in Phoenix at some point and if he wanted, I'd be glad to let him know. He replied immediately saying that he wanted me to do that and thought we might connect well for some safe play. I responded that I would definitely let him know if would be back and asked if he would feel comfortable sending me a picture of him from the front.

Shortly after sending my reply, I got an email with a great photo of him, shot in the same bathroom mirror as the first one he had sent, showing him from his shoulders down. He sported a really nice shaved, hard cock sticking straight up that was exactly what turns me on. His message said he hoped I liked what I saw and he inquired on whether I had ever done a role play.

I replied, "I really haven't done any role playing but I'd be game to give it a try." I added, "Maybe something like a coach and player scenario could be good."

"That sounds like it would be a lot of fun! I'd be up for that!" was his response.

After a bit more back and forth between us I told Jim that I had to board my plane and needed to sign off. We wrapped up the conversation agreeing to connect when I had my next trip there.

A couple weeks later I found that I needed to go back to Phoenix and I took a chance that Jim might pick up on me approaching an email to him written in role play character. I composed an email from "Coach Turner" to Jim, saying in it that I had received his application to play on the league baseball team I was coaching in his area. I said that I was looking to be in town on a certain day in couple of weeks and, if he wanted to go forward, it would be good for him to meet with me.

I suggested that I come to his house since Jim had said in our previous email exchanges that he worked from his home and that he had the house to himself all day while his girlfriend worked at an office in the downtown area. I added that my interview and screening method was a bit unique and he would need to be very open-minded about it.

Jim replied a couple of hours later saying, "Coach, it's great to hear that you are going to be here and I'd be really glad to meet with you here at my house." Over the next few days, we exchanged emails in which I said things like I wanted to make sure he was comfortable in a locker room setting with guys or that team travel and guys sharing a room would put people in close proximity and I wanted to know if he had a problem with any of that. He came back saying he was really fine with the locker room atmosphere with guys changing and sharing a room on the road would be no problem.

The back-and-forth emailing really raised the excitement level of the situation and when I confirmed my trip, Jim said he was really looking forward to the meeting and he would do anything I wanted in order for him to make the team. He gave me his location and said he would need to come get me from somewhere to escort me through the security point at the community gate so we agreed that I would call him from a shopping center in his area.

The day for my trip arrived and I flew to Phoenix and drove to the location Jim had indicated. Getting there a bit after noon, I emailed to him that I was at the shopping center and about five minutes later a sports car matching what Jim had described pulled up next where I told him I had parked. Jim got out and we shook hands. "It's great to meet you, coach. Thanks for making time for this. I'm really looking forward to doing whatever it takes to make your team."

"A pleasure to meet you, Jim. From the looks of you I think you may be just right for what I'm thinking and I'm looking forward to us getting to know each other."

"Coach, you can follow me to my house and when we get to the security gate, I'll tell them to just let you come through with me."

He was wearing shorts, a t-shirt and tennis shoes and had a youthful and next-door-guy type of look about him which I found to be very attractive. We got in our respective cars and I followed him back to his community, past the security entry point and to his house. He drove into the garage and closed the door behind him and I parked on the street and went up the front walkway. When I rang the doorbell, he opened the door and invited me to come in saying again how glad he was that we could meet.

He suggested that the guest suite off the front foyer area would be a good place to sit as it had a full conversation area with chairs, a couch and coffee table. He led the way and entering it I saw the conversation area and a room off it that was a bedroom area with a large bed. Jim got us some bottled water and then sat down on the couch and I sat in one of the stuffed chairs. We made some initial small talk as we both sat there, a bit nervous as we knew what we were looking to do.

I initiated things by saying, "Jim, I've worked out a unique system of determining if a guy has the right kind of body to play baseball well. It involves me measuring various parts of your body. Would you be OK with that?"

"Absolutely, Coach," came his reply.

I asked him to get up, took a tape measure from the briefcase I had brought and walked over to him. I had him hold his arms out to his side, unrolled the tape and measured them from a few perspectives, then measured his legs and down his back. I told him the waist was an important measurement and reached around him from the back and pulled the tape around him, sliding my hands all around his waist as I did so. I could feel him tense when I first put my hands on his hips and he stood there motionless with his arms stretched to the side as I felt around his waist and also ran my hands down his legs.

"All good, Jim?"

"Yes, coach. Just fine here," he replied.

I continued a bit more checking out his body, telling him that muscles and physique seemed good for what I had in mind. I then went around in front of him and said that to really be sure that his measurement was correct, I'd need to get the tape close against his skin, so the clothes didn't distort anything. I asked if he had a problem with that.

With what seemed like a little play-acting hesitation, Jim replied, "Well, Coach, I... ah...um...I guess that would be OK".

I sat back down in the chair facing him and said he should remove his shoes, socks, shorts and t shirt while I watched and assessed his body and he hesitantly began doing that. I just sat back casually and watched him as he took off each piece of clothing until he ended up standing there in just boxer shorts, nervousness from his excitement apparent to me. Against the front of his shorts pressed what was very clearly a hard cock inside them and I referred back in my mind to the photo he had sent that I liked so much and thought how nice it would be if he looked in person naked just the way it did in the picture.

I said to him, 'Jim, your body seems to have reacted in an interesting way to being undressed in front of me."

He stammered a bit as he explained that he didn't mean anything by it but maybe the unusual setting of being almost naked in front of me caused something to "just happen".

"Relax, Jim. This isn't the first time I've seen this kind of reaction." I then stood and went to him and began doing tape measurements, making sure to run my hands all over his smooth body as I did so. I went behind him and reached around in front with the tape circling his flat, smooth stomach and then moved my hands downward with the tape, purposely placing it too low for his waist so the tape and one of my hands fell right on the area of his shorts where his hard cock was pressing. As I did that, I pressed against him from the back so he would feel the hard dick I had pressing against the inside of my slacks. Jim reacted to the feeling of me pressing from behind into him with a slight flinch.

"You still OK with all this, Jim? We can stop if you'd like."

"Oh, no, coach. I'm fine, just do whatever you have to do," he said as I felt him push back somewhat into me. After some more measuring and running my hands over his skin I sat back down in the chair and he began to move to sit on the couch. "Oh, don't sit down, Jim. Just stand right there. I like that view," I said, looking him firmly in his eyes and then trailing my gaze down to his tented shorts. He showed nervous excitement as he stood before me and I just let him linger there, which seemed to increase the tension he was clearly feeling. After a long pause I said, "Jim, by the look of your boxers I am thinking maybe I am having some kind of effect on you here."

"Coach...um...I... well, what I'm trying to say..." he stammered out as he looked at me. I completed his sentence for him.

"I think you are turned on by me being here, you being almost naked and thinking about this turning into more than just an interview."

He hemmed and hawed a bit more, averting his eyes from me to other parts of the room and finally said, 'You're right, that's what I'd like."

"Then take off your shorts," I said firmly.

At that he put his thumbs in the waistband and slowly moved his boxer shorts down, first revealing a nice mushroom head, then a smooth hard shaft emerged into view with a nice set of totally shaved and smooth balls. He looked exactly like the picture and I was horny as hell to have this great looking guy naked in front of me. I got up, closed the distance between us and walked around him, examining his body and commenting on how each part looked. I took the tape measure and pulled it taught along the length of his dick and confirmed that he was indeed six inches long and I told him that I thought he had a very nice cock, one of the best I had seen. He thanked me and asked what I wanted him to do next.

"I want to watch you take a shower," I replied, pointing to the open door of the adjoining bathroom. "You'll be doing a lot of showering with the other players on the team and I'll evaluate how you look doing that."

Jim made his way into the bathroom with me trailing behind him. There was a walk-in shower with clear glass doors, perfect for viewing him, and I told him to start it up and get in and soap up while I watched. He did that and I watched, just leaning back on the vanity with my arms crossed in front of me. I could see the water running down over him and it was totally hot to see this slim guy soaping up and having the foam run over his chest, around his cock and down his legs.

I walked over to the glass door, opened it a bit and said, 'Your cock is rock hard and standing straight up so I'm thinking you might want some company in there with you. Is that right?"

"I'd really like that, coach."

"Then you stand in there facing me and watch."

He did that and looked through the glass at me while I stepped back a bit and slowly undressed. He ran his hands all over his wet body and began stroking his cock as he watched me remove my clothes. I was down to just boxer shorts and I stood there looking at him.

"You want to see my cock, don't you?"

"Oh, yes, Coach. I really do."

I hooked my thumbs in the waistband of my shorts and, keeping my eyes on him, I slid them down, my hard dick springing up. I let him take in the sight of me, my stiff six-inch shaved cock, with a patch of hair neatly trimmed above, and smooth, shaved balls in very open view for his enjoyment. Jim just stood there stroking his cock and looking at my hard cock in return.

"Oh, you look so good, Coach. I'd love to feel you against me!"

I walked over and opened the shower door and got in with him. I stood behind him, pressing my hard cock against his lower back and reaching around with my hands to play with his dick. He leaned back into me.

"Coach, from the first sight of you in your pictures I hoped I would get to be naked with you. This is great."

I continued to press tight against him as I played with his cock and ran my hands all over the front of his body.

"Do whatever you want with me, Coach," he sighed as he wiggled himself against my erect cock that I was rubbing on his back.

I bent my knees a bit which caused my hard dick to slide down from his lower back and between the cheeks of his smooth ass to let him feel my shaft between his cheeks, and then I moved slowly up and down to massage my cock in that nice place. Jim let out a moan and said that felt amazing. At this I turned him around and pulled him close against me so that our erect cocks were against each other and we began a slow gyration on each other as we hugged tightly and pressed our bodies together.

It felt so good with the warm water running over us and we spent a nice amount of time with our hands running all around and over each other and gyrating our hips so we could feel the great sensations of cock-to-cock grinding. We soaped each other up and enjoyed the slippery feel of our hands massaging each other's body.

"Let's take this to your bed," I said as I stroked his hard cock with one hand and held him close against me with the other.

"Yeah, that sounds good, Coach"

As we dried off, we didn't say much, he like I probably thinking about the coming time in bed together, but I commented that having the shower first was perfect as I want myself and who I am going to play with to be fresh and clean. Jim said he liked the same and we headed for the bed.

We walked out into the bedroom area and Jim laid down on his back on the bed and I followed and laid on my side snugged up next to him. We reached for each other's cocks and took our time playing with them and running our hands all over each other. I rolled over to place myself on top of Jim and with my cock right on his and he put his arms around me and pulled tightly as we rubbed our dicks together. We did this for quite some time with me occasionally pinning Jim's arms out to the side or holding his shoulders down as I arched up and rubbed my cock onto his. We both took in the sight below as we looked down and watched our cocks, enjoying the erotic feeling of each other. I then rolled over and onto my back and without breaking the connection, pulled Jim onto me so that he could be on top of me and enjoy moving himself against me as he wished. I enjoyed the feel of my hands wrapped around and rubbing his back and down his legs and pulling him against me as he rubbed away with his cock on me.

Jim then pushed himself up a bit and said, "I want to suck your Coach's cock. Can I do that?"

I told him I'd like that so he moved himself downward until his face was right above my cock, then lowered it to place his tongue onto my shaft. Jim began licking up and down my hard rod and then moved his attention to my balls and spent time licking all around and under them.

"Mmmmm," he said as he used his tongue on me, the enthusiasm of his swirling and licking indicating to me that he was really enjoying what he was doing to me. I told him that I was super sensitive in my balls and to not suck them. He continued to have a good time with his tongue, gently exploring the head and shaft of my dick and lightly licking all around my balls. It felt great to have this hot guy working me over with his mouth and I reached down and lightly stroked his hair as he worked my dick with his mouth.

Jim stopped his licking and looked up at me with an intense look in his eyes. He held my cock upright with his hand, moved his mouth to the top of it and, continuing to lock his eyes with mine, he opened his mouth and began to slowly lower his lips over the head of my very hard cock. He closed his lips around me securely as he continued lowering his mouth down my cock and as he got as much into him as he could, he stopped and held still while he swirled his tongue all around my shaft. It felt great, the warmth surrounding me and his soft tongue massaging my cock so nicely. He then drew his face upward and, when my cock popped out of his mouth, he looked me straight in the eyes again.

"Can I fuck your cock with my mouth, Coach?"

"Oh, yes, Jim, go ahead."

Jim then opened his mouth and taking me far into him he began downward and upward sucking, bobbing his head in a nice rhythm as he pleasured me wonderfully. With one hand, he lightly held my balls and, when he extended his fingers to tickle the sensitive area below them between my legs, the intense pleasurable sensation caused me to jerks my legs straight apart. It felt fantastic and he stopped to tell me how excited it made him, then returned to sucking my very erect shaft and playing his fingers all around my highly sensitized balls.

"That is so good, Jim. I love you fucking my cock with your mouth," I said, reaching down, placing my hands on each side of his head and then starting a gentle thrusting of my hips to move my hard dick in and out of his mouth. Jim's lips tightened around me as he and I moved in unison with each other and the feeling was great and I was incredibly turned on.

"Jim, would you like Coach to lick your dick?"