I had a great night’s sleep. Being held by Roger I felt safe and protected. I like the feeling of his arms around me holding me tight against his body. And I have to admit, (at least to myself) I like the feeling of his cock snuggling between my ass crack.
It was about 6:00 in the morning and I had to get up to pee. I slipped out of bed and tried to be as quiet as possible while I made my way to the bathroom. In the bathroom I realized I was only wearing a tee shirt, so I pulled it off and threw it on the floor next to my boxer shorts.
By this point Roger had shifted positions and was lying on his back. I got back into bed and laid on my left side wondering if Roger was going to fuck me. We both had sex a few hours ago so maybe he wasn’t ready. Anyway, I drifted back to sleep.
I began waking up again maybe an hour later. This time Roger was definitely awake. His hard dick was poking against my naked ass. I felt good and after last night with Carolyn, I was glad that Roger was still interested in fucking me.
His cockhead soon located the entrance to my hole and started pushing its way inside. In my half-awake, half-sleep state, I was totally relaxed and his cock found little resistance from my body. Once his cockhead made it past my ass ring, he stopped and rested a while, allowing me to adjust to his invading shaft. Last week when Roger first fucked me, I was fully awake and aware of what he was doing. This time, I was almost in a dream state. I felt like my body was floating above the bed watching Roger’s cock work its way into my hole.
He was all the way inside me now. Roger’s cock was rubbing up against my prostate, almost massaging it. I was in ecstasy and feeling so much pleasure. I was wondering if Carolyn felt this way when I was fucking her pussy last night. If so, then I’m happy I was able to pleasure her the way Roger was pleasuring me.
I was lost in time, so I had no idea how long roger was inside me. When he did eventually come, he let out a load, audible groan as he filled up hole with his cum. Just as his last pelvic thrust hit my prostate, my own cock erupted and shot my hot cum all over the sheets. I couldn’t remember the last time I came without touching my own cock.
Once he deposited his seed inside me, Roger stayed inside me and we both drifted off back to sleep. I woke up for good around 9:00 and discovered I was alone. Roger must have gotten up earlier without me noticing. I reached behind me and felt his dried cum on my ass and on the sheets. I was happy to discover that my ass was not very soar at all.
Getting up, I walked naked to the room across the hall to get my toiletries and fresh clothes before jumping into the shower. After showering, shaving and dressing, I made my way downstairs to find Roger in the kitchen drinking coffee and working on his laptop.
“Good morning, Kyle. I trust you slept well.”
“Um, I did. I’m still trying to process everything that happened last night.”
“Well, I’m here if you want to talk. In the meantime, grab yourself some coffee and have a seat. I’m making pancakes.” I poured my coffee while Roger got up and started prepping our breakfast.
“My only question is, did you have fun?”
“I did,” I relied.
Roger came up behind me and squeezed my shoulders and said “Good.” He didn’t try to kiss me or invade my space. It was as if he was allowing me to determine how close or intimate we should be.
Of course, the pancakes were delicious. Is there anything Roger can’t do well?
Roger continued to type away on his laptop while I checked my email and the basketball scores on my phone. I wasn’t feeling ignored or left out but I was curious so I asked, “What are you working on? Something for work?”
“Oh, I’m just finishing up my speech for this afternoon. I mentioned that I have an event today. I’m the chairman for the HRC fundraiser and they asked me to give a speech. Basically, it’s a plea to give money. This is one of their biggest fundraising events of the year.”
“HRC?” I asked.
“Sorry, HRC is the Human Rights Campaign. They are the largest LGBTQ civil rights organizations in the country. They fight for equality for all queer people. They have a number of fundraisers throughout the country and this is one of their largest. There are a lot of gay people on Martha’s Vineyard. You’re welcome to join me or if you’re not up for it, you can stay here or I can drop you off somewhere.”
“What do you know, I thought HRC was the Hard Rock Café. What kind of event is it?” I asked.
“Basically, it’s a cocktail party with lots of hors d’oeuvres and lots of alcohol. It’s being held at the Vineyard Haven public library. The dress code is business casual.”
I figured, what’s the harm in going? “Okay, I’d like to go and check it out. I’d like to hear your speech. Is it okay if I’m not LGBTQ?”
“It’s perfectly okay. There will be plenty of allies there as well. Don’t worry, no one will be checking your “Gay Card” at the door.”
We enjoyed our breakfast and while Roger finished his speech, I did some reading then took a walk outside. I was surprised to see how close his house was to the beach. I took a walk along the beach and thought a lot about Roger and how weird our situation was. I like spending time with him and I really appreciate how he never pushes me to do more than I’m willing to do. He never tries to kiss me or hold my hand like a lot of my former girlfriends. He also hasn’t tried to get me to suck his cock. I don’t even know if I want to suck his cock anyway. He seems to be happy with how things are right now. So am I.
We left around 3 in the afternoon. The event went from 4:00 – 8:00. As one of the chairpersons, Roger had to show up early. I wandered around the library while he met with the folks in charge. I checked out the auction items and thought back to two weeks ago when I was part of an auction. Fortunately, there were no “bachelors” being auctioned tonight, only art work, restaurants and experiences like white water rafting or hot air balloon rides. Everything was out of my price range. It was fun checking out the items while I drank my “signature cocktail” and ate the delicious hors d’oeuvres.
By 4:00, people were starting to arrive and by 4:30 it was packed. The crowd seemed very fancy to me. I felt a little underdressed in my jeans and sweater, but I didn’t let that affect me. I pride myself in being able to get along in any situation.
It was now 5:30 and the program was starting. I looked around for Roger but couldn’t find him anywhere. Eventually I spotted him standing next to the stage, probably waiting for his turn to speak. However, before I had a chance to walk over to him, a young man, approached Roger and gave him a hug. Roger responded by giving this young man, practically a boy, a kiss on the forehead. Roger was beaming at this guy and was obviously exciting to see him.
Who is this guy and what is he to Roger? The bigger question was, why am I feeling jealous toward him. Roger and I have no commitment or any real relationship. We’ve only known each other for a few weeks. I shouldn’t be feeling this way.
Eventually, Roger noticed me standing in the crowd. He gave me a little wave and taking this young guy by the arm headed toward me.
“I’m going on in a couple of minutes but Kyle, I want you to meet my son Henry. Henry, this is Kyle. He’s staying at the house with us this weekend.”
Henry and I shook hands while we exchanged “nice to meet yous”. Before Roger returned to his position near the stage he said, “Henry, can you keep Kyle company. He doesn’t know anyone here.”
I felt very foolish. Looking closer at Henry, of course he was Roger’s son. He looked so much like him. I should have figured it out. I found out that Henry was 21 years old and a junior at Yale (Roger’s alma mater). He is a history major but plans on going to law school after graduating. He took the ferry from Rhode Island this morning and plans to go back to school on Monday. Also, he’ll be staying at the house with me and Roger. Great, I thought. I hope he doesn’t get in our way.
“So, tell me Kyle, are you and my dad dating?”
“Well, no. We’ve only met a few weeks ago.” I wanted to tell Henry that I am straight, not gay, but I couldn’t find a way to say it.
“No worries, it’s just that we haven’t meet many of the guys dad has dated. Besides, you seem to be his type, younger, good looking and athletic.”
I blushed a little when he said that. He asked about my job and I told him about working construction and being a minor league baseball player.
“That must be it.” Henry said, “Dad loves baseball. My Mom tells me I was named after her Father, but Dad says I was named after Hank Aaron. And my brother Carl was named after Yastrzemski. Only Abigail, or Abby avoided a baseball reference name.
We paused our conversation to listen to Roger’s speech. He was great. He was commanding, eloquent, humorous in some parts and personal. Roger spoke passionately about the work that the HRC is doing for the community and how we all need to continue to support their efforts.
While listening to Roger’s talk I strangely had a feeling of pride toward him. That was weird, why would I be proud of someone I hardly know. When he was done, he received a well-earned round of applause.
“That’s my dad for you”, Henry said. “He always shines in these public settings. He’s both a great role model and a hard act to follow. You know, he’s always been there or me and my brother and sister. Even after he came out as bisexual. He makes sure we know we’re his top priority. Now that us kids are getting a little older and more independent, with lives of our own, I wish he would find someone and settle down.”
Was that comment addresses toward me, I wondered.
“He’s a great catch.”
“Yes, that he is.” I replied hoping he wasn’t trying to play match maker.
While chatting some more, I learned that Henry came out as gay during his freshmen year of college. I don’t know why I was surprised by that, but I was. He was at a fundraiser event for an LGBTQ organization, but then again so was I. Henry mentioned how difficult it was to come out as gay, even with having a bisexual father. He then asked me if I had a difficult time coming out. Why are people always assuming I’m gay?
Fortunately, Roger joined us before I had a chance to answer. We congratulated him on his speech. I’m sure he is experienced speaking in front of much larger and less friendly crowds.
Henry took off to see some friends and announced he would be home late. Roger and I wondered around, talking with different folks and having a few more signature cocktails. Of course, Roger knew most of the people at the event and he made sure to introduce me to everyone he spoke to. I made a point of paying attention to how Roger introduced me. He never called me his “friend” or “date”. It was always, “This is Kyle Ehrhart”, or “Let me introduce you to Kyle Ehrhart”. No one asked questions and everyone, especially Roger made me feel welcomed.
We left the event a little after 8:00 and I was feeling kind of tipsy. I’m glad I decided to attend the event. It was nice meeting his son Henry and I enjoyed spending time with Roger and seeing him give his speech. He was in his element.
Back at the house, we tried to relax and unwind by watch some TV. The Bruin’s game was on but it was difficult to concentrate. It was a long week at work, not to mention our sexual escapades with Carolyn on Friday night not to mention today’s event. We were both pretty wiped out. By 10:00 I couldn’t keep my eyes open any longer. Roger announced he was heading up to bed but I should stay up and watch the rest of the hockey game if I wanted.
All I wanted was to sleep so I followed Roger upstairs. Remembering that Henry was coming back to the house tonight and realized that my clothes and toiletries were still in his room, I went into his room to retrieve them. Forgetting that there were three other bedrooms to select, I subconsciously brought my stuff to Roger’s room.
He crawled into bed while I was still brushing my teeth. He didn’t say anything about me being in his room and while he didn’t invite me to share his bed tonight, I knew he wouldn’t mind. After brushing, I stood by Roger’s bed and observed him for a moment. He looked so handsome and peaceful with his eyes closed. I walked around to the other side of the bed, pulled off my tee shirt, dropped my boxer shorts and slipped into bed next to him. We were both sound asleep within minutes.
Sunday morning, I woke up and once again I was alone in bed. I got up, peed, washed my face, brushed my teeth, threw on some clothes and headed downstairs.
Roger and Henry were already in the kitchen and as I approached heard part of their conversation.
“So dad, tell me,” Henry said, “Is Kyle your boyfriend? Are you two dating?”
“We’ve only known each other for a few weeks. He’s a nice guy and we are just getting to know each other.”
“Well, you are sleeping together. Right?”
“I’m not going to discuss my sex life with my son.”
“Fair enough. He’s very handsome and masculine. I find him very sexy.” Henry responded. “If you’re not dating him, maybe I should ask him out.”
“Careful Henry. Don’t cross a line.”
Henry chuckles, “Dad, I am joking. I would never. Besides, how old is Kyle anyway.”
“He’s 31.”
“There you go. I only date guys in their 20’s. Actually, I’m half-joking. But seriously, Kyle is a great guy, and I want to see you happy.”
“Thanks, I appreciate that. But things are complicated, Kyle identifies as straight.”
“Oh, I didn’t realize.”
“You know as well as I do how complicated sexuality is. Kyle is on his own path. If he identifies as straight, I respect that.”
By that point, I had heard enough and coughed a few times, so Roger and Henry knew I was about to join them in the kitchen.
Roger said he was waiting for me to come down before starting breakfast. We drank our coffee and talked about how we planned to spend our Sunday while Roger cooked us omelets. Henry planned to meet up with some friends and Roger hoped to spend a quiet day at home. He said it was rare not to have something scheduled. A quiet day at the house sounded good to me.
Henry hung out with us for a while then left around 1:00. Henry was a good, level-headed kid with a plan for the future. It was nice to see him have such a good relationship with this father. They actually talk and listen to each other and Henry seems to really respect Roger’s opinions on things. It’s a very different dynamic to what my dad and I have. We never talk about anything important.
Sunday afternoon turned out to be a relaxing, stress free, day with Roger. We took a long walk on the beach, we played backgammon, we read a little and when it came up that I had never seen the movie Casablanca, Roger insisted on stopping what we were doing and watch it right away. I was reluctant to watch some old, black and white, hundred-year-old movie, but I have to admit, it was pretty cool. I liked it and glad Roger suggested we watch it.
When the movie was over, it was about 6:30 and getting pretty dark outside.
“The weekend seems to be winding down”, Roger started. “I’m glad you were available to join me. Hope you had a good time too.”
“Yeah, it was a blast. You have a beautiful home here and I enjoyed meeting your son Henry too.”
“A highlight for me was Friday night with Carolyn.”
“Same for me.” I replied. “As I said, I had never been in a threesome before. It was hot.”
“It was, and it was incredible to be part of a threesome with you. I loved watching you fuck her, I have to say, it was such a turn on. Just thinking about it now, it’s getting me a little excited.”
I looked over to Roger and saw a noticeable raise in his pants. Thinking of fucking Carolyn and how much Roger enjoyed watching us got my cock to stir as well.
Roger must have noticed my cock getting bigger. He moved closer to me on the couch and put his hand on my crotch. “Would you mind a little afternoon attention?”
“Not at all, be my guest.” I was happy to receive another one of Roger’s blowjobs.
Roger slid down to the floor in front of me and spread my legs apart. He then unbuttoned my jeans and pulled down my zipper. Reaching in under my boxer shorts, Roger pulled out my semi-hard cock.
“Your cock is so beautiful.” Roger stroked my cock a few times as it grew to it’s full 7 inches. He lowered his head and kissed my cockhead. He then continued down my shaft kissing it along the way. When he got to my balls, he attempted to stuff them in his mouth but they were a bit too big to fit. Instead, he kissed and licked all over and under my balls. It felt so good.
Returning to my cock shaft, and with a combination of kissing, licking, sucking and tongue swirling, was really getting me off. Roger was proving to me once again what a great cocksucker he truly was.
After about fifteen minutes of worshiping my cock, I knew I was about to explode. My legs were propped over Roger’s shoulders as my cock was buried in Roger’s mouth. I couldn’t believe he was deepthroating my entire 7 inches.
As my orgasm built and built to its explosive finale, I grabbed Roger’s head and kept it in place over my cock. I erupted, sending shot after shot of my cum down Roger’s throat. Like the world class cocksucker he was, Roger swallowed every drop.
As my cock started deflating, Roger lifted his hear. He then proceeded to lick my cock clean.
“How was that? Did you enjoy it”?
“Yes, very much. That was amazing. Maybe the best blowjob I’ve ever had.”
“Good, I’m glad.” Roger stated, “Now it’s my turn.”
Oh no, I thought. Does Roger expect me to suck his cock now. I’m not sure if I’m ready for that. What do I do? Maybe I should try.
Roger, gently guided me face down on the couch. Ok, he doesn’t want a blowjob, he just wants to fuck me. He then pulled my pants and underwear down below my butt, exposing my hole.
“Such a beautiful sight. Your ass is just as gorgeous as your dick. I can’t get enough of it. It’s irresistible.” Roger started by kissing each of my butt cheeks. I was overcome with anticipation, knowing what was going to happen next.
Soon, he spread my cheeks and ran his tongue from the top of my crack to the bottom. He repeated that a few times while I moaned and whimpered. Next, he targeted my butt hole and started probing it with his tongue. Man, that felt amazing. I never knew how awesome it felt to have your butt rimmed before but it’s quite addictive.
Between his tongue, saliva and now his fingers, my hole was pretty ready for what was coming next. Roger stood up and said he’d be right back, leaving me and my butt exposed on the couch.
Upon his return, Roger squirting some lube into my hole and began pushing it in with his fingers. Eventually he removed his fingers from my hole and replaced them with something else, something firm and hard.
“What is that?” I asked trying to turn my head.
“Just relax Kyle’, Roger said in a soft voice. “I’m using a dildo on you. Have you even used a dildo before?”
“No, I haven’t”, I replied, “I’ve never even seen one before.”
“Well, it’s obvious you enjoy anal stimulation. It’s another version of ass-play.” As Roger continued to insert the dildo into my ass, he continued, “Consider it another opportunity to expand your horizons, trying new things.”
When the dildo was fully inserted, I was feeling pretty stuffed, Roger once again got up and said he’d be right back. I felt a little foolish, lying on the couch, fully dressed with my pants pulled down below my ass and a dildo pushed inside me.
When Roger returned, he was naked from the waist down and his cock fully erect. He stroked his hardon a few times while applying lube to it.
“How does the dildo feel inside you?” He began pushing it in and out of me.
“It feels okay. It makes me feel full, if that makes sense.”
“I wanted to open you up as much as possible and I figured you’ve never used a dildo before. I wanted you to have that experience.”
The dildo finally come out of my hole with a “pop”. Roger straddled me, then lined up his cockhead with my hole. Between the rimming, his fingers and the dildo, I was so turned on, I was pushing my hips up to meet his cockhead. I was encouraging it to enter me, to pleasure me. It was more than just wanting his cock, I needed it.
The dildo did its job, Roger was fully inside me in no time, and he was resting on my back.
“Oh my god. Your ass feels amazing Kyle. I love how you make my cock feel.”
He began thrusting slowly in and out of my hole.
“Do you like how that feels Kyle?” I didn’t respond to Roger’s question. He continued fucking me, picking up the pace while I laid there in a state of bliss and ecstasy.
After a number of minutes, Roger asked again, “Kyle, do you like me inside of you?”
I couldn’t deny it to Roger or myself any longer. “I do, I love how you feel inside of me.”
“I’m glad Kyle. I want to make you feel good and this is the ultimate way two men can give each other pleasure.” With a load grunt, Roger filled my hole up with his hot cum.
“Don’t move”. For a third time, Roger got up and left me on the couch, this time, bare assed with his cum beginning to leak out of my hole. I don’t know where he thought I’d be going.
He came back a moment later with a wet washcloth and began cleaning my ass of all the cum and lube. With a second washcloth he dried it. I remained laying on the couch recovering from our fuck session.
Just then, we heard a car door close. Oh shit, Henry is home. Roger grabbed the lube, the dildo, the washcloths and ran upstairs while I pulled my pants back up and buttoned my jeans just before Henry come in the front door.
We ordered take-out for dinner and the three of us enjoyed the rest of the evening. Since I needed to be at work at 7:30 am the next day, I needed to get up at 5 to begin my return trip to Boston. I headed up to bed at 10, leaving Roger and Henry alone in the living room.
“Since I won’t be up when you leave in the morning, let me say my goodbyes now.” Henry stood up and gave me a warm hug. “It was a pleasure meeting you, Kyle. I hope to see you again soon.”
I went up to Roger’s room and quickly fell asleep. At some point he joined me in bed but I never heard him come in. Roger got up to see me off and make me coffee. When the car showed up at 5:30 to drive me to the airport, he gave me a hug goodbye and said what a great time he had this weekend.
It’s crazy, I was somehow back at my construction site by 7:30. I was back to my ordinary life as a construction worker and semi-professional ball player. My life is so far removed from the lifestyle I experienced with Roger this weekend.
And speaking of Roger, I left without us making any plans to get together again in the future. I hope he contacts me because I don’t even have a way to contact him.
To be continued.
