Dorm Room Dilemma

Off To Denver

The alarm came way too early Friday morning for Ryder and me. Our bodies intertwined in sixty-nine position, hearts hammering out rapid beats, throbbing cocks engorged with blood as we thrashed around on my bed sweating, while blowing the fuck out of each other. We couldn’t get enough of each other’s cocks. I wanted Ryder to fuck me but we didn’t have time; so instead, we sucked each other to fruition devouring a breakfast of cum.

After mind-blowing oral sex, what a fricking awesome way to start the day, we untangled our bodies before showering and dressing. By four-thirty a.m. the Uber driver called to confirm pick up. Needless to say, our asses were dragging when the driver picked the two of us up, and then the driver drove to Dan’s Bar and Grill where he picked up Tyler to drive the three of us to Easterwood Airport.

During the ride to the airport Ryder and I dozed intermittently, but I noticed Tyler kept nervously bumping and rubbing his leg against mine in what I considered might be a flirtatious manner. Once we arrived at the charter service Ryder whipped out his credit card attempting to pay for the three of us. The charter operator waved Ryder off saying, “The flight’s paid for, a round trip gift to the Staff Sergeant for his service as well as two guests.” We all thanked the pilot and others before putting our bags on the plane and then boarding.

Before takeoff the pilot gave his customary safety briefing and then he announced the distance, travel time and cursing altitude as well as the temp on the ground at Centennial Airport. By the time we reached cruising altitude and speed the three of us, sitting in the back, began talking and drinking complimentary drinks, discussing the next two weeks. Tyler asked, “So, where bouts is your house?”

“The family compound that’s been in the family for years is located on a little over 60 acres that backs up to the mountain in the small town of Breeze Spring. Town population around 300, just a four way stop, southwest of Denver, off the 470, in the Indian Hills area,” Ryder said. “Pretty rural, but we’ve got Internet, cell service and indoor plumbing.”

“Sounds cool,” Tyler said laughing at Ryder last part of the description. “You know I got to be back at the bar to work on New Year’s Eve Day and New Year’s Day. Big 24-hour biker blowout, but if I can get rides I’d like to return as soon as possible after New Year’s Day to spend the rest of winter break with you guys.”

“Let me speak to my dad regarding flights,” Ryder said.

For some reason, I’d been getting what I perceived as strange flirtatious vibes from Tyler since seeing him naked in his room behind the bar. Whenever together he kept looking at me with what I considered come-hither looks. Ryder and I discussed Tyler the evening before and both of us wondered whether he might be gay or at least bisexual, but what if he wasn’t? We decided sometime before Ryder’s friends arrived we’d subtly broach the subject with Tyler about his sexual orientation before letting him in on things.

Ryder asked, “So, what type recreation y’all into?”

Ty and I replied with little laughs, “Anything and everything.”

“There’s a lot to do when we get there. However, from what dad tells me, winter sports such as skiing and snowboarding as well as snowmobiling might be limited, depending on snow, but we can always load up and head to high country to the west to find snow,” Ryder said.

“Improved my skiing while in the Army…I attended the Army’s BMC up in Vermont,” Tyler said.

“BMC?” Ryder questioned.

“AMWS, Army Mountain Warfare School, BMC, Basic Mountaineering Course,” Tyler replied. “I been snowboarding and snowmobiling in upstate New York since a teenager.”

“Cool,” Ryder and I replied in unison.

Tyler asked. “So, how many people gonna be at this shindig?”

“Christmas Eve and day probably just my family members; however, after they depart on Tuesday my gang will begin arriving for the rest of the week and into the first week of January…Three of my high school buddies already confirmed, maybe three more, all depends,” Ryder said.

“Any chicks?”

“Nope, an all guy thing.” Ryder said.

“So, no sex?” Tyler asked.

“Maybe, maybe not…All depends,” Ryder replied glancing at Rob.

“Depends?” Tyler asked.

“Depends on what you’re into,” Rob said, “could be some sex if you don’t mind a little spice in life.”

“What’s that supposed to mean?” Tyler asked.

“Look dude, I’m probably gay. Don’t know for sure, but the way things been goin in my life looks like it,” Ryder confessed. “Night before last I discovered Robby enjoys sex with guys too, so if you want to join in you’re more than welcome…To be blunt, this vacation is all about blowjobs and butt fucking among guys.”

“Well Hell’s Bells guys, why didn’t you all say so in the first place,” Tyler said with a big grin.

Tyler revealed that although he identified as straight while in the Army he’d experimented sexually with boys as a teen. “I prefer sex with guys more so than chicks…I found other guys in the Army that enjoyed sex together too.”

As the conversation continued we were surprised to discover Ty had been thinking about us individually all semester during classes we attended with him, but we never picked up on any of his covert signals. I thought to myself, what is it about me? Did I have an invisible gay magnet somewhere on my body?

Once we discovered Tyler might be amenable for a ménage a trios or more we filled him in on what lay ahead for the next two weeks. We told him that when not engaged in winter sports there’d be a lot of time for sex.

“Ty let me take the lead making introductions to family members and others once we all arrive,” Ryder said. “I told my mom you’re coming with, but no details.

“Sure, no problem.”

For the next few minutes Ty began filling Ryder and me in on his background. Then Ryder asked, “So, Ty, are you into sharing, group sex or just monogamy? Let me know what you’re into, so I can put things together. You know, make arrangements.”

“Okay,” Tyler said, “I’m game for just about anything and everything…It’s been a long dry spell for me. I just want to cram all the sex possible into this vacation…I want my nuts drained by the time spring semester starts.”

“Cool,” We replied in unison.

“One important question…Are you two lovers or anything like that? Cause I don’t want to be the bad guy interloper breaking up a relationship. I just want to enjoy blowjobs for the next few days,” Tyler said.

Laughing Ryan finally said, “Hell, the two of us,” pointing to each other, “didn’t even know the other to be into guys until the other night.”

“So, for lack of a better word, you guys are just sixty-nine buddies…You know, kinda like jack off buddies back when we were kids,” Tyler said.

“Exactly,” Ryder replied. “So, what transpires between all of us during winter break is a secret and stays between us on the mountain here in Breeze Spring.”

“Cool,” Tyler said, “surely there’ll be a lot of first time experiences for all of us?”

The pilot came on the intercom to make the announcement that he was on final approach, to make sure our seat belts were fastened. He said, “Temp on the ground a little chilly, 42 degrees, sky’s clear and no snow at Centennial.”

Once our aircraft landed and stopped in the designated parking area we donned our winter jackets before deplaning and then got our bags. Of course, we again thanked the responsible party who’d paid for our flight, and then called to see who might be available to pick us up. Ryder’s mom answered saying that she’d pick us up at the airport in about an hour. Ryder informed his mother we were going to try to get a ride to the McDonald’s, just outside the airport. “I’ll text where we’re at.”

After eating we waited for Ryder’s mom to show up. She arrived about 45 minutes later in a black Lincoln Navigator 4X4. With introductions made we threw our gear in the back. Tyler and I sat in the back seat while Ryder rode shotgun next to his mom. First question Ryder asked, “Who all’s at home?”

“James and Sarah,” Ryder’s mom replied. James and Sarah are a live-in married couple who take care of everything including housekeeping and cooking at the compound. “Your dad and grandpa are in Denver and they’ll be home this evening.”

“So, anyone call for me mom?”

“Couple your friends wanting to know when you’ll be in, and what the plan for after Christmas.”

Ryder didn’t expect the sex marathoners to arrive until the day or next after Christmas. His mom asked or more like informed us that we’d have to be patient, because she needed make some stops to do some last-minute shopping in Littleton. “Cool,” Everyone responded, because Tyler and I needed to do some shopping too.

Mrs. Pleasance pulled off the southern beltway and drove to Littleton for last minute gifts, food, drinks. She admonished Tyler and me not to eat a lot of candy or junk food because Alaskan Sockeye Salmon and sides was the bill of fare for the evening dinner. Ryder accompanied his mom shopping, so he might explain to her who the last-minute guest, Tyler was, and why he was with us and more about me. Before we split up Ryder’s mom asked our dress shirt sizes.

In the meantime, after giving Mrs. Pleasance our dress shirt sizes, Tyler and I took off together looking for some last-minute gifts and other items. I hadn’t gotten anything for Ryder or Tyler not to mention Ryder’s parents. I didn’t have much money to spend. Mom had sent me $300.00 dollars for Christmas, so I decided on boxes of candy and other small acceptable gifts.

After Ty Googled where he could buy Alaskan Amber we were off to the store. He bought a couple six packs, and I bought him a couple as Christmas gifts. After shopping Ty and I stopped at the local coffee shop for large coffees and decided, even though a little chilly, we’d drink outside, so we might talk, more privately. Outside Tyler spoke up asking, “So, you and the big guy just started having sex?”

“So far, just making out, frotting and a few blowjobs …Nothin serious…No butt fucking,” I replied. “In fact, we exchanged mind blowing blow jobs before we picked you up this morning.”

“No wonder you two were sleeping on the ride to the airport.”

I explained how I got hooked on sex with boys when I was younger and how things began with Ryder parading around our dorm room naked all semester. “I’d been admiring his junk all semester, and then the other night we got into conversation and in no time, we were in bed. The rest is history.”

“So, you guys kiss?”

“First time kissing a guy for me, but turned out to be kind of enjoyable along with the nipple play and frotting…That’s far out.”

“You’ve seen me naked how do I measure up between you guys?” Tyler asked.

“You and me, probably bout the same size, but Ryder, he’s got a monster mother fucking porn star cock hangin on him…At least seven and half maybe eight inches long and at least six inches in girth. But his fuckin cockhead is frickin huge with a big purplish corona.”

“Wow! That is porn star pecker material.”

“I can only get maybe couple inches of that motherfucker in my mouth and ain’t no way I can deep throat it,” I said, “kinda squeamish about him tryin to fuck me in the ass with that big frickin log.”

“Damn! Never been butt fuck yet,” Tyler said. “Heard about it and seen it a couple times on porn videos…You have to tell me more about it.”

“Same here,” I explained. Hell, I wanted to show my new friend all about anal sex not just tell him about it. “I’ve been watchin a lot of porn videos the past months trying to learn more about anal sex. I also ordered a dildo to attempt to get my asshole prepped.”

I continued explaining about my ongoing fantasizes regarding anal sex and the dildos I’d purchased online and been using to prepare my ass for penetration. I confided in him that I wanted Ryder to fuck me, but hesitant because of his size. Of course, Ty was curious. He wanted to learn more and see my little friends.

“I think I’d rather exchange blowjobs with you before trying to take Ryder’s big porn star meat from what you tell me…So, never kissed a guy what’s it like to kiss another guy,” Tyler asked.

“Kinda cool…I’ll show you when we get someplace private, hopefully we’ll get paired in the same room tonight.”

“Cool,” Tyler replied. “Hell, I ain’t kissed that many chicks.”

“So, you’re a little bit of a novice like me?”

“Just jack off and a few blowjobs, that’s about it for me,” Tyler said. “Now that I’m out of the Army I think it’s time to get me a jack off or sixty-nine buddy.”

“I’ve been secretly droolin over you since I saw your cock back in your room…Dude when I saw your cock when you stepped outta the shower I wanted it. If I’d known, I’d been all over that thing for sure.”

“I tried to present it hopin you might take a hint, because I was ready to sixty-nine with you.”

We sat sipping our coffee thinking about what each other had said; probably, each of us thinking what we wanted to do to the other when we got some privacy. Suddenly, Tyler said, “You know, Ryder’s mom is one hot ass lady,”

“Yeah, wonder how old she is?”

“Probably in her 40s, if I use simple math,” Tyler said. “I wonder what my mom would’ve looked like if she hadn’t been killed.”

I didn’t feel like responding to that: maybe another time, another place. My phone sounded the familiar Ryder ringtone interrupting my thoughts. “Yeah, okay, see you in a few at the car…We’re at the coffee shop down the street,” I said and disconnected the call.

The two of us finished our coffee, picked up our bags and began walking back toward the car. Of course, we talked more along the way. The more time I spent around Ty the more at ease I felt. I decided that the leg rubbing maybe a nervous twitch from his time in the Army.

A horn sounded behind us and the Navigator stopped. We got in and Mrs. Pleasance asked, “What kinds of doughnuts or pastries do you boys like for breakfast? There’s a great pastry shop further down the street and you know how your dad and grandpa enjoy pastry with coffee son.”

From the back seat, we chimed in about our favorite doughnuts. A stop at the pastry shop and then off to get on the southern beltway to take us to the Pleasance’s compound. I thought about Tyler and me exchanging blowjobs that night on the drive to Ryder’s house—maybe more—maybe a threesome.