The bachelor auction where I first met Roger was at the end of September. Our first date was the beginning of October and our weekend trip to Marta’s Vineyard was mid-October. It is now early January and I haven’t seen him since.
To be fair Roger told me he was heading into a very business period at work. He had back-to-back business trips to New York and Washington and then it was a surprise trip to London that lasted ten days.
We spoke on the phone a few times but all our phone calls were short and direct. He never said he missed me or couldn’t wait to see me again. I was beginning to feel like a jilted school girl. Maybe my apprehension to suck his cock, fuck him or even kiss him has turned him off. I couldn’t get over my hang-ups about gay sex and I was afraid to admit to myself that I might be bisexual or even gay. I was holding on to the idea that I was still a straight man.
Of course, I enjoyed fucking that woman Carolyn when I was in Marta’s Vineyard last October. Then again, Roger was with us and that added to the excitement. It’s one thing to enjoy getting my cock sucked by Roger but another thing entirely to enjoy getting fucked by him. It was getting more and more difficult to reconcile that with my identity. Am I no longer straight? Am I bi or even gay now?
In early December Roger informed me that he was spending Christmas break with his ex-wife and kids on a ski vacation to Vail Colorado. It was something they had been planning for a long time.
I spent Thanksgiving and Christmas with my parents, two sisters and their families while enduring their endless questions about when I would meet a nice girl and settle down. They are under the false impression that I date all the time, a different girl every night and endless sex. If only they knew the truth. I tried going out clubbing with some of my friends but I just wasn’t into it.
It’s not that Roger totally forgot about me. A week before Christmas, a package arrived at my apartment. It was a Christmas gift from Roger. The note read: Dear Kyle, Thinking of you and hoping you have a spectacular holiday. Roger.
The gift was a signed Ted Williams baseball card. It was framed as well. This must have cost a fortune. How did Roger even know that Ted Williams is my all-time favorite player? What a wonderful, thoughtful gift. And to think, I haven’t gotten him anything. But what can I possibly get him, the man has everything?
By mid-January and with no word from Roger in over a month I was beginning to think he had moved on and forgot about me. Was it time for me to move on too?
Then on January 15th I received a call on my cell phone.
“Hello, is this Kyle Ehrhart?
“Yes, it is.”
“This is Kevin, Roger Thatcher’s assistant. Mr. Thatcher asked me to contact you and see if you are available to join him on January 19th for a special Boston Pop’s concert honoring Martin Luther King Day. It takes place the Sunday night before the MLK holiday at Sympathy Hall.”
“Oh, hi Kevin. It’s good to talk with you again. How are you doing?”
“All good”, Then a long pause, “Can I tell Roger, excuse me, Mr. Thatcher you will be able to join him?”
“Yes, you can let Roger know I will be there.”
“Okay, very well then. He will pick you up at your apartment at 6:00.”
I got off the phone feeling great. Roger hadn’t forgotten about me after all. I’ve never seen the Boston Pops before and have never been to Sympathy Hall, so that’s great as well. Also, I have the Monday holiday off from work so I won’t have to get up early the next day. Maybe he’ll invite me to stay overnight.
When Monday came around, Roger showed up at my apartment in his BMW and off we went to dinner then the concert. He made reservations at Ostra. Apparently, it’s one of the best sea food restaurants in Boston, but I’ve never heard of it.
Of course, the food was scrumptious, the service phenomenal and the atmosphere was top notch. I wouldn’t expect anything less from a restaurant Roger suggested. When we were seated, we finally got a chance to talk.
“How are you doing Kyle? You seem a little pensive. Is everything okay?”
“Yes, I’m fine”, I said. “It’s just that I haven’t seen you in three months. I thought you might not be interested in spending time with me anymore.”
Roger’s expression turned serious as he said, “Kyle, that’s not true. I hope you know that I very much enjoy your company. I find you endlessly fascinating and it’s been a pleasure getting to know you. I think very highly of you.” What he said made me feel much better.
“Unfortunately, it’s been an unusually busy time for me at work; with lots of travel. When I’m traveling for work, I tend to focus only on that. With meetings, projects, long hours and time differences I don’t always get a chance to reach out and call. I did manage to call a few times though.”
“You did, I appreciate that,” I replied. “It’s just that I have to wait for you to call me. I don’t have any way to even contact you.”
“Oh, I’m such a dummy sometimes. I didn’t realize.” Roger reached his hand out to me and said, “Give me your phone.” When I did, he typed something and gave it back to me. “There. Now you have my personal cell number. Whenever you want to talk, just call. If I’m in a meeting or busy, leave a message and I’ll call you back as soon as I can.”
“Thank you. I appreciate that.” I paused for a moment before continuing, “Also, when you do want to see me it’s always through your assistant Kevin. It’s kind of weird.”
Roger chuckled a little, then said, “I suppose you have a valid point there. Kevin is a tremendous asset to me and he helps keep my life on track. Going forward, I will make every effort to make my own phone calls to you.”
That was helpful. But there was something else on my mind. I was practically whispering so neighboring tables couldn’t overhear us. “One other thing. I’m afraid that I’m not enough for you,”
“What do you mean, Kyle.”
“When we’re together, you know, in bed, we do the same thing. You’ll blow me and then. . . “ It was difficult for me to continue and finds the right words. “you know, you come inside me. I’ve never sucked or fucked you.”
Looking very serious, Roger scooted his chair closer to me to give us more privacy and leaned his head close to mine. “Kyle, if this is what you’re worried about, don’t let it concern you. I am totally satisfied with what we do together in bed. I am fully aware that you have never been with a man before. All this is new to you. I suck your cock because I enjoy it and it gives you pleasure. You let me fuck you because I assume you enjoy it and it gives me pleasure.”
“I would never expect you or pressure you to do something that you didn’t want to do or wasn’t ready to do. Believe me, I never thought we would have even one sexual encounter together, so I’m counting ever time we’re together a bonus.”
“I appreciate you saying that. I was nervous that I wasn’t satisfying you.”
“One other thing Kyle. I know you identify as straight, and that’s fine. You have every right to identify your sexuality for yourself. You’re attracted to woman. Well, so am I. When we had that threesome with Carolyn in Martha’s Vineyard, it was one of the hottest, most erotic experiences I ever had. Part of that was seeing how much you were enjoying yourself. I loved seeing you in action. You were much more active and in control than when it’s just the two of us. When it’s just the two of us, you are much more passive. That’s not a criticism, just my observation.”
“Bottomline, I’m perfectly happy to continue doing what we’ve been doing. If you want to explore and try something new, great, let me know. If not, that’s fine too. If you want to invite another women into our bed, I’m up for that as well.”
I took a deep breath to calm myself.
‘One thing I would like to ask you Kyle. In the future if we’re together, and I’m, as you say, “inside you”, would you be willing to change positions? Remember when we were together with Carolyn. You were fucking her from behind, you know, doggy style, she suggested changing positions, and she said, and I quote, Kyle, I want to see your pretty face. That’s all I’m asking. I also want to see your pretty face, not just the back of your head.”
I did my best to explain my feelings. “I’ve been thinking a lot about this and I believe, somehow that if I just lay there passively and not participate and let it happen to me, then I can disassociate and somehow it’s less gay. I know that sounds ridiculous but I have some deep-seated hang-ups about sexuality. I grew up in a very homophobic household”
“Human beings are very complicated. And I’ve sorry you grew up in that kind of environment.”
“Let me think this through some more”, I replied. “Let’s talk after the concert.
We finished our dinner and I prayed to God that no one was overhearing our conversation. Roger paid the bill and we headed over to Symphony Hall. The building was a great example of renaissance architecture. It was beautiful and the acoustics were perfect. When the concert was over, we hurried back to Roger’s car. It was a very cold January evening in Boston.
When we were safely inside his warm car, Roger turned to me and said, “So, Kyle, would you like to come home with me?”
“I would like that, yes. And I’ve been thinking about what we talked about over dinner. I think I’d be willing to change and try other positions.”
“That’s wonderful, Kyle. We will only do what you feel comfortable with.”
Driving back to Roger’s apartment, I pondered what was in store for me and if I’ve crossed over from straight to gay once and for all.
It was about 10:30 when we entered Roger’s place. Since it was understood that we were going to have sex we went straight to his bedroom. Roger began to undress and I soon followed suit. Roger was completely naked in no time while I was still in my boxer shorts and tee shirt. I looked over at Roger’s naked body and really observed it, perhaps for the first time. I admired his lean yet muscular physique, his smooth chest and striking blue eyes. I admit he is a very handsome man.
“Kyle, sit down at the end of the bed”, Roger commanded. I pulled down my shorts and sat. Roger knelt between my legs and took my cock into his mouth. He started sucking me as my cock grew to its full length. As always, his mouth felt amazing on my throbbing cock.
After five or so minutes, Roger stopped and stood up. “Stand up Kyle.” I stood and Roger wrapped his arms around me and pressed me tight against his body. He stared into my eyes the entire time. It was intense and I felt very connected to him. Roger ran his hands up and down my back and over my ass, giving it a squeeze and a playful slap. I did the same, running my hands over his body and holding him close to me.
Roger soon stopped and left the bedroom saying not to move and he’d be right back. When he returned, he was carrying a straight-back wooden kitchen chair and a bottle of lube. He placed the chair a few feet from the bed and sat down. Patting his thighs, he said, “Kyle, come and sit on my lap.” I walked over, straddled his legs and sat down. It felt a little strange for a grown man to be sitting on another grown man’s lap but I went along with it.
“I’m not too heavy, am I?”
“Not at all, Kyle.” He was holding me tight, keeping me in place. Both our erected cocks were pushed up against each other. It felt weird but kind of okay.
Reaching down, Roger picked up the lube and squirted a generous dollop on both our cocks. Grabbing both our cocks with one hand he stroked us both which spread the lube along our shafts. That felt incredible as well. Roger reached up and took my right hand and moved it over to our cocks. He soon replaced his hand with mine and I was now the one stroking our cocks together. I’ve never jerked off a guy off before, this was another new experience for me.
With his hand no longer jerking our cocks, it was free to reach behind me and he began fingering my hole. His lube coated fingers took no time breaking through my ass ring and soon two and then three fingers were inside me. With the stimulation of my cock by my hand and my ass by Roger’s fingers, I was starting to get turned on and breathing heavily.
“Okay Kyle, I would like you to stand up and turn around.” I did as he suggested. “Now sit down on my dick.” Roger guided his slick cock into my ass, as I began sitting down again onto his lap. Roger rubbed my back as I slowly impaled myself onto his firm, hard cock. When he was about half way inside me, Roger wrapped his arms around my chest and pulled me close, forcing his entire cock into my hole.
The jolt of his cock hitting the bottom of my hole, forced a whimper and a groan from my throat. Roger kissed my neck and soothed me by saying, “You’re doing great Kyle. I am so proud of you. Once you’re ready move around. You’re in charge.”
While I got use to his invading cock inside my hole, Roger rubbed his hands over my hairy chest and tweaked my nipples. That sent an electric charge through my body. No one’s ever tweaked my nipples before. Wow.
“You have such a manly chest Kyle. I love running my hands over it.” When I was accustomed to Roger’s cock in my ass and any discomfort subsided, I began rocking back and forth and moving my hips up and down. “I’d like to try another position. Can you move so we are facing each other?”
I got up and turned around, once again straddling Roger’s lap, I slowly lowered myself onto his cock. We were now face to face, staring into each other’s eyes. My hard cock was pressed against Roger’s stomach and his hands were on my back holding me close against him. Being in this position I believe that Roger was able to get further inside me then he ever had before. I’m certain his cockhead was poking against my prostate sending pleasure waves throughout my body.
Never breaking eye contact, Roger put his hand on the back of my head and slowing brought our lips together. We kissed passionately while Roger’s tongue probed my mouth. I was moving up and down and all around, practically bouncing on his cock. Things were building up fast and I was afraid I was going to blow my load.
Roger slowed his kissing and with his hands on my hips kept me from moving too much. “Kyle, I’d like to try something. You’re a bigger guy than me so I’m going to need your cooperation.”
“Okay, what should I do?” I asked
“I’m going to stand up, along with you. You need to keep your arms around my neck and when I stand, you need to wrap your legs around my waist as tight as you can.”
“Are you sure?” I asked.
“Just trust me.” I nodded my head in agreement.
When Roger stood up, I quickly wrapped my legs around his waist. He had one arm under my ass and the other around my shoulder blades. Also, his cock was still firmly inserted inside my ass. He stood there for a moment to ensure he had his balance, then walked the three steps toward the bed. He gently lowed me on my back with him on top of me. Somehow, his cock never dislodged. It was as if we were one being, no longer two.
Being lifted and carried by Roger was the most intimate, erotic and freeing experiences I ever had. I simply let go of all my inhibitions and fears and just lived in the moment.
Once on the bed, on my back, Roger lifted my legs and draped them over his shoulders and started pumping furiously in and out of my ass. My arms were around his neck and I kept kissing Roger over and over again. I think he was getting close to cumming and so was I.
“Let’s switch positions. I want you on top of me.” Roger rolled to his right and we turned so he was now on his back and I was on top, sitting on his cock.
I started moving up and down, riding Roger’s cock. It was a nice to be in charge instead of just lying there.
“That’s it.” Roger stated, “Ride me. Take my cock. Make it feel good. That’s my man.”
Hearing Roger call me “my man”, sent me over the top and I started squirting shot after shot of cum all over Roger’s chest. Simultaneously, Roger grabbed my hips and filled my hole up with his cum.
I collapsed on top of Roger as his slowly shrinking cock finally exited my ass. He put his arms around my neck and gave me a kiss on the lips.
“That was beautiful”, he said. “There is nothing as wonderful as one man giving another man the ultimate pleasure. And Kyle, you give me so much pleasure.
After a quick clean up, we returned to bed. This time we fell asleep, not front to back, but face to face. Our semi-hard cocks pressed against each other. It was a night to remember.
To be continued.
