One benefit of working in construction is I get off work at 3:30. This gave me plenty of time to get home shower and pack before a car arrived in front of my apartment to drive me to the airfield. I was alone in the car, just me and the driver who took me to Norwood Municipal airport for the 53-minute flight to Marta’s Vineyard. I got dropped off in front of a building which served as a main terminal. I was alone. No one was there to meet me.
I was starting to feel uneasy and forgotten about when a black Lincoln Town Car pulled up. The door opened and out came a young, well-dressed man in his twenties, followed by Roger. Finally, there he is.
Roger quickly walked over to me, putting his hands on my shoulders and giving me a little shake said, “I am so glad you were available to join me this weekend. We’re going to have fun Kyle.”
The young man who arrived with Roger stood next to us wheeling a suitcase. “Kyle, let me introduce you to Kevin Cronin. Kevin is my assistant. He is really my right hand man and I couldn’t get by without him. Kevin, this is Kyle Ehrhart.” Suddenly Roger’s phone rang. “I got to take this, it’s my son,” walking away for privacy leaving Kevin and I along.
I put my hand out to Kevin and said, “Yeah, we spoke on the phone, nice to meet you.” In return, Kevin just glared at me and didn’t shake my hand. Okay, that was kind of rude.
His only response to me was, “I hope you’re not going to take advantage of Roger; I mean Mr. Thatcher.”
“What do you mean, take advantage?
“I’ve been Mr. Thatcher’s assistant for a few years and have seen a number of men throw themselves at him. Let’s face it, he’s rich, well connected and very handsome. I don’t want him to get hurt.”
“I think Roger can take care of himself. Besides, I’m not gay.” When I said that, Kevin chortled a little.
What’s this guy’s deal? Who does he think I am, some kind of tramp looking for a sugar daddy? That’s not me. Fortunately, Roger had returned from his phone call.
“Okay, Kyle we should probably get going. Kevin, when those numbers come in, send them to me right away. Sorry, you’re unable to attend the event tomorrow.”
Kevin replied, “That’s fine. There’ll be other events. I’ll see you back in the office on Monday”. That got me wondering. Is there some kind of event that I’m supposed to attend with Roger? I have no idea what’s on the agenda for this weekend. I guess I’ll just play it by ear and see what happens.
Kevin got back into the Town Car and left as Roger and I walked around back to the air strip. There a Cessna jet was parked with the door open and the airstairs down. A guy who looked like the pilot was standing at the bottom waiting to greet us.
“Good evening, Mr. Thatcher. Welcome aboard.”
“Thanks Cal. Are we ready to take off?”
“As soon as you’re settled.” We climbed aboard and took our seats. We were the only two passengers on the plain. In all my life I had never seen such luxury. I’m use to flying coach.
“Whose plane is this?” I asked. “Do you own it?”
Roger just laughed, “I’m not that rich. My bank has a lease agreement with the company. We order one when needed. I do a lot of business travel and we find this a lot more convenient.”
The ride was pretty smooth, and we landed in Martha’s Vineyard in under an hour. Once there, we took an Uber to Roger’s beach house. When I hear beach house, I think of the little two or four room shacks my family would stay when we went to the Cape for vacation. What Roger should have said was mansion. His place was huge, with five bedroom and six bathrooms. There was even an inground swimming pool and hot tub. Why someone needed an inground pool when you were so close to the ocean, I’ll never know. Roger said his three kids and ex-wife spend a lot of time here in the summer and on holidays so they needed a place big enough to accommodate everyone. Plus, the kids often like to invite friends to visit.
“Well, we’re here. I don’t know what your expectations are for this weekend, but…”
Roger quickly responded, “I have no expectations. You were such a good sport on our date last week, I just wanted to treat you to nice weekend. No pressure, we’ll do whatever we want. I have an event tomorrow that I have to attend, but other than that, I’m just here to relax. I thought you would enjoy a nice relaxing weekend was well.”
“Sounds good.” I replied.
“Great, let’s get settled and get something to eat. I don’t know about you, but I’m famished.” We went up the stairs to the second floor and down the hallway. Roger showed me all the bedrooms. “This one is mine, but please feel free to take any of the others. They are all very comfortable.”
I choose the bedroom across from Rogers. “I’ll take this one. I hope you don’t mind.”
“Not at all. As I said, no pressure.”
I got settled into the room. From the décor, I figured it was one of his son’s.
“Hey Kyle, let’s go out and get something to eat. Let me know when you’re ready.” We took an Uber to a great micro-brew in town. Since it was off season, the place wasn’t that crowded.
We enjoyed our burgers and beers at a table near the bar as well as the atmosphere.
“Kyle, I wanted to check in with you and see how you’re doing. I was pleasantly surprised when you accepted my invitation to go away for the weekend.”
“Well, to be honest, I said yes before I had a chance to think about it too much. First of all, I’ve never been to Marta’s Vineyard and didn’t’ want to miss the opportunity. Also, I had a good time last week and you’re great company. Besides, you said we can just be friends. There is no pressure for us to do anything else.”
My heart was pounding in my chest. I hope that Roger couldn’t tell that I secretly hoped he would fuck me again like he did last week. I couldn’t tell him that I actually enjoyed being fucked by him. I could barely admit it to myself.
“Absolutely, whatever you want Kyle. As much as I enjoyed what we did last week, if that’s all that happens between us, then I’m fine with it. I feel like I can connect with you; as a person, not just a bed mate.”
“I’m glad you said that. I agree, I like spending time with you, and with what happened with us in bed, as you said, a person should be open to new experiences.” I paused for a few moments then continued, “Never in my life did I think I would let a man do that to me.”
Roger picked up his beer glass and held it up as a toast and said, “Well, here’s to new experiences”. We clinked glasses. Then Roger continued, “And don’t forget, you didn’t object to what we did. You never said no.”
That is true. I never tried to stop Roger from fucking me. Maybe deep down I wanted him to. And I did enjoy it. What does that say about me? I can’t think about that now. I tried to change the subject.
“I have to ask, does you assistant Kevin think we’re dating?”
“What? Why would you say that?”
“When we were at the airport, he warned me not to take advantage of you.”
Roger laughed so hard at my statement that some people at the bar turned to look at us.
“That’s hysterical. I don’t think I have to worry about you taking advantage of me. I’m not that naïve. Kevin is just a young kid. I hope you weren’t offended by his remarks.”
“Not at all. But curious, have the two of you ever . . . “
Roger cut me off before I could finish my sentence. “Absolutely not. I’m his boss. It wouldn’t be appropriate. Yes, Kevin is gay, but there has never been anything but a strict business relationship between us.”
“What about that guy Tim? The one we met at the Celtic’s game.”
“Yes, Tim and I had a relationship but we were always co-workers, never boss/employee. I think I mentioned that Tim was my first serious relationship with a man. I really loved him and while he ultimately decided to go back to his wife and family, I have only good feelings about him and our time together. It helped me come to terms with my sexuality. In fact, just to be completely honest with you, Tim and I still get together a couple of time a year to have sex.”
“Really?” I was a little surprised. “You get together for sex even though he’s married?”
“It’s not ideal, but Tim’s wife knows he’s bisexual. She knows we had a relationship in the past and still get together on occasion. Besides, the way we see it; if Tim has an itch that needs scratching, it’s better that I do the scratching then him meeting up for some hookup with a random guy. They know me and they can trust me. I don’t see anything wrong with that and we’re not hurting anyone.”
“I guess”, I responded. “No judgement from me. What two consenting adults do, is no business of mine.”
“Glad to hear that.” After a pause, Roger continued, “I have a question for you Kyle. I hope it’s not too personal but after what happened between the two of us last week, do you still consider yourself straight?”
“Well, yes I do.” I thought about this some more. “What we did was fun and I’m glad we did it. Maybe having sex with you was more of a onetime experiment for me. I’m not saying I would never do it again but I’m definitely attracted to woman.”
“Fair enough.” Roger said, he then looked about the bar. “Tell me this Kyle, is there anyone at the bar that you find attractive?”
I looked around the bar. Since it was off season it wasn’t very crowded. There was a young man and woman sitting together at one end. There was a single woman in the middle and an older guy with a beard and pot belly drinking a beer and watching TV at the other end. Of course, there was also the bartender. He was about mid-thirties, and with a goatee. I admit, he was good looking. I really hope Roger wasn’t trying to steer me toward the bartender.
“The blond woman sitting by herself. She’s the only person I’m attracted to.”
“She’s beautiful”, Roger mentioned, “What is it about her that you like?”
“Well, she looks classy. Very put together, from her hair and makeup to her clothes. It looks like she takes care of herself and her appearance.”
“You don’t think she’s too old for you? She looks closer to my age then yours Kyle.”
“Not at all. Age never mattered to me.”
With that, Roger got up, gave me a slight nod and walked to the bar. He stood next to the woman and started chatting her up. He called the bartender over and ordered more drinks. Roger got the woman laughing and it seemed like she was enjoying his company. It looked like he was trying to charm the pants off her, like he charmed the pants off me.
When the new drinks arrived, Roger and the woman gathered them up and headed toward our table.
“Kyle, I’d like you to meet Carolyn. Carolyn, this is Kyle. Please take a seat. Carolyn is here by herself and I thought we could use some company.”
It turns out that Carolyn was a 44-year-old, single mother of two. She lives in Newton Mass. and works as a development director for a small non-profit in Boston. Her divorce was just finalized this week and she was feeling down. On a whim, she decided to leave her kids with her parents for a week and rent an Airbnb in Marta’s Vineyard. While Roger was doing a lot to keep the conversation going and was his usual charming self, Carolyn was focusing most of her attention toward me. She complemented me on my curly hair, on my biceps and loved the fact that I was a baseball player. Even someone as naïve and clueless as I am, I could tell she was coming on to me.
What am I going to do now? I was staying with Roger and I was secretly hoping he might fuck me again. Is Carolyn going to mess everything up? Is Roger going to be mad if I hook up with this woman?
After a half hour and another drink, Carolyn got up and excused herself to go to the lady’s room. This gave Roger and me a chance to talk about what was happening. As soon as Carolyn was safely out of earshot, Roger began laughing. “Well, my boy. It looks like you’re going to get lucky tonight.”
“Don’t laugh!” I pleaded. “What are we going to do? I think she definitely wants to sleep with me, or us.”
“Maybe we should let her. My motto has always been not to let an opportunity pass by. And you’re a straight man and I’m a bisexual man and we’re both attracted to her. She’s a lovely, sexy woman who is going through a rough time. We’ll make her day.”
When Carolyn came back from the restroom, she sat even closer to me, put her hand on my knee and looked me right in the eye. Once again, I let Roger take the lead. “Carolyn, it’s been such a pleasure getting to know you but It’s getting kind of late. Since I live so close, Kyle and I were wondering if you would like to join us back at my house and continue getting to know each other.”
“Both?” was Carolyn’s response.
“Yes, both.” Roger said that with such confidence and directness. From my own experience, I know when he gets like that, he is hard to resist. Roger stood up and extended his hand to Carolyn, “Shall we?”
“Why not. I’m on holiday and it could be fun.”
We gathered our belongings, and we headed out. Carolyn had her own car so she drove us to Roger’s. When we got there Carolyn, and I just stood in the entranceway. Both of us were uncertain of what to do next. Roger took care of that.
With a big grin on his face, Roger took hold of Carolyn’s hand with his right hand and my hand with his left. He then walked backwards, leading us toward the staircase. We climbed the stairs, walked down the hall and entered Roger’s bedroom. Once there, Roger embraced Carolyn and gave her a kiss on the mouth. He did the same to me, embracing me and giving me a kiss on the mouth. He then pushed me and Carolyn together encouraging us to kiss.
Once we had our first kiss, we were off and running. We made out passionately and our hands roamed each other’s bodies. Carolyn felt my arms and groped my ass. I also grabbed her ass and cupped her breasts. Soon Carolyn turned her back and asked me to “unzip” her. I pulled down the zipper to her dress which she quickly wiggled out of as it dropped to the ground. She kicked off her heels as she stepped out of her dress. There she was, just standing there in her black lacey bra and panties.
She started to unbutton my shirt while I kicked off my shoes. When I started unbuckling my belt, she stopped me and said she wanted to do that herself. Once my belt was open and my pants unbuttoned, they fell to the floor.
I was just wearing my boxer shorts and socks while Carolyn was still in her bra and panties. We embraced and made out again while I slowly backed her up to the bed. She laid down on the bed and I laid on top of her. I was grinding my crotch into her and I was fully erect and leaking precum like crazy. Just then, I thought, Where’s Roger? Where has he been and what is he doing?
I looked around, then saw him over my shoulder standing at the foot of the bed. He was fully naked. He soon joined us in the bed while exploring both our bodies with his hands. He then reached under Carolyn and unfastened her bra. Seeing this I moved things along by pulling Carolyn’s panties off and doing the same with my boxers. Now, the three of us were completely naked.
I got back on the bed and the three of us laid there, side by side by side. We kissed and explored, and it was very exciting. Carolyn’s hand was on my dick, Roger’s hand was on my dick. My hand was on Carolyn’s boob and Roger’s hand was on Carolyn’s boob. I have never experienced such a trilling supercharged sexual experience before. I was on fire. I was a tiger ready to conquer whatever is in my path.
I moved down Carolyn’s body and found my way to her pussy. I stuck two fingers into her and discovered she was plenty wet and ready for whatever I would give her. It had been a while since I ate out a pussy so I wanted to make sure I took that opportunity. As my tongue entered her, she started bucking like a wild woman. I looked up to see what Roger was up to only to see Carolyn sucking Roger’s cock. I wondered if she was as good a cock sucker as Roger was.
When my 7-inch cock started entering Carolyn’s pussy she stopped sucking Roger’s cock and began to moan. Roger looked over at me and nodded his approval. Her hole was tight and wet and warm.
We were in a bit of an awkward position with me at the foot of the bed fucking Carolyn’s pussy and Roger at the head of the bed getting his cock sucked, so he suggested a position change. He had Carolyn get in the doggy position with me fucking her from behind and Roger kneeling in front of her getting his cock suck. What an improvement, it is more comfortable for all of us.
Roger looked at me and gave me a big smile, then winked at me. I returned the wink and a smile. Soon we locked eyes and I was only focused on Roger. I concentrated on his face, his handsome face. Even though I was fucking Carolyn, it was if she wasn’t even there. To me, it was like I was pumping my cock into Roger. That thought scared me and thrilled me at the same time.
“Carolyn, I’m about to cum”, Roger announced.
Briefly pausing, Carolyn proclaimed, “Give it to me!” And from the contortions on Roger’s face, I knew he was filling her mouth with his seed. Just the sight of that almost put me over the edge. I had to slow my pace in order not to cum immediately.
After depositing his cum in Carolyn’s mouth, Roger retreated to the bathroom to clean up. Carolyn then suggested another change of position. “Kyle, I want to see your pretty face.” She then rolled over onto her back again and I reentered her. She looked very beautiful staring up at me.
Roger returned from the bathroom and stood behind me. I could sense his presence, and I could feel his breath on the back of my neck. When I bent down to kiss Carolyn, I could taste remnants of Roger’s cum on her lips and tongue. I then noticed some of his sperm had dribbled down on to her chin. I reached down and scooped it up with my tongue. I had never tasted another man’s cum before. I found it oddly appealing. Just then as I was licking Roger’s cum from Carolyn’s chin, Roger stuck a finger into my exposed butthole, causing my cock to explode inside Carolyn.
I yelled out as my cock filled her pussy with my cream. From her guttural groans and short, gasping breath, I knew Carolyn was reaching climax. With her arms wrapped around by neck and legs wrapped around my lower back, it kept us interlocked and in place. My cock was firmly planted inside her. I could feel the muscles of vagina spasm as we rode out wave after wave of her orgasm.
When her orgasm subsided, I rolled over next to her. Roger joined us in bed as the three of us shared our intimate moment. Not many words were shared as we stroked and fondled each other. Eventually Carolyn announced she needed to be going. The three of us got up went to different bathrooms to clean up agreeing to meet downstairs in the living room when we’re ready.
Roger and I finished up first and waited for Carolyn. He was wearing a beautiful silk bathrobe, and I had on boxer shorts and a tee shirt.
“Man, that was intense,” I said.
“It certainly was.” Roger responded.
“Believe or not, that was my first threesome.”
“I’m glad I was able to help facilitate it. And be part of it. You looked magnificent making love to that woman Kyle. It was so hot. As I said before, it’s always good to experience new things.” I could feel myself blushing.
Carolyn appeared with a big smile on her face, slowly descending the staircase. She came over to where we were standing and gave each of us a kiss on the lips.
“Roger, Kyle, you have no idea how much I needed this tonight. I was feeling very depressed and now I feel like I have a new lease on life.”
We talked a little more before Carolyn eventually left. Since it was after midnight Roger and I decided it was time for bed. He locked the door and turned out the lights as we climbed the stairs to the bedrooms. Roger entered his room, and I went to the one across the hall.
I tried to sleep but just tossed and turned. I couldn’t settle down. After about twenty minutes, I got up and crossed the hall. I entered Roger’s bedroom and stood at the foot of his bed. Here is the bed I just had a threesome in and here is the man who fucked me last week. What am I doing here? What do I want from him? I had so many mixed emotions and feelings I didn’t know what to do.
I thought Roger was sleeping but apparently, he wasn’t. He turned slightly and lifted the blanket, inviting me to join him in bed. I slipped in and snuggled up against his body. He wrapped his arm around me and held me close. His hand slid down to my hip and lifted the waistband of my boxer shorts.
“Lose these,” was all he said. I shimmied down my boxer shorts and tossed them to the floor. When I returned to our snuggle position, I could feel Roger’s semi-hard cock nestled in the crack of my ass. It felt so good. I felt comfortable and safe and cared for. As I started to drift off to sleep, I thought about the events of the day. I then thought about Carolyn and the sex we had. I had no idea at the time that she would be the last woman I ever slept with.
To be continued
