Failed Connections

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

And then, gripping my buttocks in his hands and spreading them wide to give him maximum access while his fingers still spread across my narrow hips, he started stroking me in long, hard-fought thrusts, fucking me hard and fast as I cried out in passion and begging for mercy that didn't come and that I didn't really want. When he came, after I'd done so, bringing myself off again with my own clutching hand, he jerked out of me, tore the condom off, and arced his cum on my belly and chest.

Without a word, he gathered up his trousers and briefs and went through to my bedroom and into the bathroom. He closed the door and I heard the lock engage and then the shower start. He didn't want me to join him in the shower. Dragging myself up from the sofa, I staggered into the bath off the second bedroom and cleaned myself off with a wet washcloth.

It had been brutal and cruel, and it had finished much too soon. It was everything I could have dreamed from a thuggish James Bond. I wanted more. I went back into the master bedroom. I stripped the bedspread down to the footboard, climbed on and stretched out on the bed, shoving a pillow under the small of my back to lift my pelvis up.

When Buddy came out of the bathroom, he was fully clothed. He looked at me and said, "I hope the beer is still cold." Then he sauntered back out to the living area.

I waited for ten minutes or so and then rolled out of the bed and padded out to the living room. He was gone and the beer glass had been drained.

I wanted him to do me again—properly, in the bed. I needed him to do me again. I wasn't proud. I'd call him at his hotel. I'd offer him money to come back and stuff me again and to ride me hard. I wracked my brain to try to remember what hotel he was staying at. He'd said it was near here, but I don't think he told me which one it was. He'd told me so little. He'd answered nearly none of my questions about himself, and those he'd answered, he hadn't done so fully. When I was asking him about Baltimore, he didn't take the hint that I was angling for an invitation to come see him there.

All I could remember of what he had said was about his fetish with slim hips and tight fits. I'd met his expectations there and he'd played out his fetish. So, why wasn't he clambering for a repeat?

The next day I called the offices of the Denver Dynamites soccer team, but they wouldn't give me any information on any of the players. I called Baltimore, and the offices of the Baltimore Blast weren't any more helpful. I could send fan mail and he'd answer if he wanted to. I sent fan mail but he didn't answer. I went on the computer but he wasn't listed on the dating site anymore.

I even went to Baltimore, to a Blasts game, but that was months later, and he'd moved on. I found he'd gone to the Atlanta Silverbacks. By then, I'd hooked up with Owen through the dating service. He was big cocked too, like Buddy. And he did me well. Not as cruelly and magnificently as Buddy had done me that one time, but well enough. And Owen stuck around. So, slowly, ever so slowly, I became accepting that my one encounter with the thuggish James Bond, as exciting as it had been, was just a failed connection. We had wanted something different from each other.

* * * *

I knew that he'd claimed the ticket and come to the rodeo because each of the riders had his or her own four-seat box for each performance at the Colorado Springs Rodeo, and he was sitting in my box. Even though I couldn't see him clearly from where I was perched on the chute fence, ready to take my turn on the bull, I knew it was him. I knew he'd still have that interesting scar running from his left ear to the corner of his mouth. I knew that, where it should have marred his looks, which looked like he'd been a few too many fist fights already, it didn't. It didn't hide that he was handsome in his own rough way, just as his clothes couldn't hide what I'd seen in the photos he'd sent me.

He, Buddy Wright, was the only one in the box because I usually invited students of mine from the previous year—my first one as a high school music teacher in the Denver suburb of Littleton—but I couldn't risk them sitting with a man I'd hooked up with on the Internet, a man I hoped was going to fuck me that day—a man who had seemed obsessed with how narrow-hipped I was, possibly the first time that I thought that been slim-waisted and -hipped was seen as arousing by a man.

I'd gone to an Internet dating service because I was lonely and felt under a microscope in my first year out of college, teaching. I couldn't hook up with anyone anywhere near Littleton—not as a high school teacher—not hook up with another man. I needed someone at long distance. Not necessarily a one-night-stand. I did want a relationship, but someone who wasn't living here.

Baltimore, Maryland, was a longer way away than I had been looking for, and I hadn't shown much interest in Buddy when he first contacted me via the dating site. We'd hooked up mostly because we were both into sports. Our hookup on the Web had deepened because he'd found that I was unusually narrow-hipped. He was a pro soccer player with a Baltimore indoor soccer league, and I'd been riding the bulls since high school. So, that's where we started. He wanted to talk about bow hunting as well as soccer but he lost me there, and then the discussion moved on to where we both were headed when we signed up for this hook-up site—to sex.

He asked for a photo and I, being self-conscious of my size and my equipment, had sent one from the waist up. I'd been bold enough to send one of me bare-chested, but only from the belly up. He'd remarked on my size, asking me if I was sure I was of age. I answered that I was twenty-one and just small for my age. He responded with a photo of him completely naked. His body was beautiful. He wasn't tall or bulked up, in keeping with what a soccer player needed—to be trimmed for speed on his legs—but he was hung like a bull.

Along with that photo, he asked me for one of me that showed my lower body as well. I wouldn't have sent one, but he also spoke of his fetish, which was for small men, especially ones with an androgynes look, boyish equipment and very narrow hips. He said that my photo indicated I was "pretty" and might at least be narrow in the hips. How narrow was I? He made it sound that what he was looking for was exactly what was making me reticent to try to hook up with a guy—what I saw as a turnoff for an athletic guy who I would find arousing. I didn't think athletic guys who were into guys would be into "girlish" guys like me. There was no question that I found Buddy Wright arousing from his photos and from his e-mail discussions. His was a Mediterranean-type, curly dark-haired god from his photos. A perfect body for a soccer player. The size of his cock was intimidating, but I'd dreamed of taking something like that. The few times I'd had sex with a man, I wanted to be stuffed and stretched to the limit. At his prompting, I revealed this fetish of mine.

In turn, he reiterated and focused in on his fetish for narrow hips and tight fit. When I revealed that I was thirty-one inches at the hips, his e-mails came more often and more intimately. He wanted to meet. He would be in my area. He wanted to fuck me.

I just wanted to be fucked by an athletic stud so bad. I, Toby McLean, the new music teacher at Littleton High and semipro bull rider in rodeos around Colorado, wanted to have someone fucking me periodically. I just didn't want that want to get connected with being a high school teacher in the Denver suburbs. I was happy that his interests were focusing in on my narrow hips and tight channel.

He had to ask again, assuring me that he had this fetish about narrow hips, boyish genitals, and tight holes. "You say you haven't done it often, that your partners have always remarked about how tight you are, how narrow your hips and tight your buttocks are. Don't be shy about that, if it's true. Send me photos of your pelvis. Also, can you let your hair down in the photo?"

So, I did. There didn't seem to be any reason not to bring it to a head at this point. Either what I had was what he wanted or it wasn't. I didn't hold back. I sent full frontal photos, side photos, photos from the rear, pelvis photos, and even, because he specifically asked, a photo of me bending over, spreading my cheeks, and showing my tight hole. I usually kept my hair in a tight bun at the back of my head, especially when I was in the classroom, but, for these photos, I let it down to reach down to my shoulders. I measured my hips again. Yes, thirty-one inches, I let him know, having checked to find that that, indeed, was a very narrow measurement. It normally should be the same as my chest, which was thirty-five inches and had been, when I thought I wanted to transcend, been augment a bit into something more womanly.

I was afraid he'd think I was a freak and call it all off, but his response claimed he was thrilled. "Can't wait to hold you steady there between my hands, in the hollow of your hips, and be inside you, and to hold and squeeze your breasts as I move inside you" he'd answered. I masturbated to the image of that.

He messaged back that he would be in Denver, playing a soccer game with the Denver Dynamite indoor soccer team at their arena in Castle Rock, in July and he wanted to meet me—not just meet me; he wanted to fuck me. I told him that the Colorado Springs Rodeo would be going on in July and I'd be riding the bulls nearly every day. Castle Rock was between Denver and Colorado Springs. If he gave me a day he could be at the rodeo, I'd make sure he had a ticket and we could go from there.

"I'm a bull too," he wrote back. "Confirm you want to ride me."

I held my hands over the keyboard for a few minutes before I responded. But wasn't this why I'd gone to the expense and effort to sign up with this dating service—more of a hook-up service? I confirmed that that was exactly what I wanted.

I checked when his team, the Baltimore Blast, would be in Denver in July to play the Denver Dynamite, and, without letting him know, I got tickets to their game in Castle Rock. During the game, I picked him out on the field and followed him. I was looking for evidence that he wasn't all that he had messaged he was, but everything I could see—although I had to imagine I could see the facial scar—panned out. At the end of the game I found where the visiting players would come out of their locker room and stationed myself there. Maybe I'd catch him there and we could hook up before he came to the rodeo.

But when he came out of the locker room, he was with an older guy, a slim, good-looking blond guy who probably was in his late thirties and who looked like money. What I noticed most was how slim and androgynous, almost plastic, the guy looked—and how narrow his hips were.

So, I wasn't the only hookup Buddy Wright had arranged in Denver. I felt deflated, but I'd gone this far already. I couldn't back out now or I'd probably never be brave enough to ever do it again. The guy Buddy left with looked like money, but he looked old. I was confident that I could deal with that. I bet the rich guy wasn't going to take Buddy to a sports bar where local sportsmen hung out. I'd done some thinking and I found a sports bar in Denver where both soccer players and bow hunters gathered. I bet that would put Buddy into the mood.

Not that I got the chance.

I came out of the chute early in the competition I'd sent Wright a ticket for and stayed on the bull for seven of the eight seconds I had to cling to its back to qualify to go on to the next round. I managed to roll out and away without sustaining any hurt other than to my dignity. I hadn't gone out in the first round since I'd gone on the circuit. I marked that up to Buddy Wright being in the stands and what I was thinking about what we'd be doing later that night, if the hookup went as planned. So, I was running a good bit ahead of myself there.

At halftime, when the second round of rides by cowboys you had held on for eight seconds or more in the first round would reappear in a second round, I went up to introduce myself to Buddy Wright and tell him what I had in mind for us to do after the rodeo was over. I admitted that I'd gone out early because I was thinking of him and he had the kindness to say he gathered that from looking at my stats in the program. I still had to be there for the finale, I told him. He didn't give me a chance to tell him about the sports bar I'd found.

"Is there someplace we can go now. I want it now," Wright said. "You say you don't have to be back here until the end. We've got time. Is there someplace?"

"Well, yes, we have trailer where we can go if we need to rest or take care of an injury that doesn't require a hospital and ambulance." I wanted to get across that bull riding was a macho sport.

"Does the door lock from the inside?"

"Yes, and there's a safety latch so even a key wouldn't work from the outside."

"Let's go there now."

The trailers were small, more or less one compartment with a kitchenette and john at one end of it. But they did have locks on the door. He pushed me to my knees as soon as we entered the trailer I led him to and locked it, and I was sucking a cock that was every inch as big and thick as the photographs he'd sent indicated it was. While I did that, he was bent over me, undoing the bun at the back of my head and letting my hair cascade down to my shoulders, running fingers under the waistband of my jeans and checking out how tight I was. He made sounds of approval. And then, when he was hard and throbbing, he pushed me back into a chair, and stripped off my shirt, jeans, and jock, leaving me naked.

I wasn't naked for long, though. He had a briefcase with him, and he opened that now and took out a silky red slip and a pair of red spike heels. He put those on me and, for a few minutes, he ran us hands up under the hem of the slip and felt me up. Then he put my ankles on his shoulders, with my high-heeled feet on either side of his cheeks, bunched the slip up around my waist, bent me almost in two, and attacked my small cock and balls and my hole with his fingers and mouth, having brought his own lube.

I wanted so much to tell him we had time and I had a surprise planned for him that would maybe bring us closer together in the start of some sort of relationship, but he was having none of it. Before I knew it, he had a red silk scarf stuffed in my mouth and he was bent over me, pushing that big cock inside of me, declaring his appreciation for how tight I was and how difficult it was to bottom in me. He was squeezing my hips between his hands, spreading his fingers out, trying to make the fingertips meet. He held me like this the whole time he was pumping me.

As I panted hard, cried out through the muffling gag in my mouth, and dug my nails into his shoulders, trying to push him away at first but then holding him to me when he was in and stroking me and taking me to heaven, he fucked me hard and fast. He turned me, facing into the chair, got behind me, grabbed my hips in his hands again, laughing by being able to nearly touch his fingers while encasing my narrow hips, and penetrated me again. He ran his hands up under the hem of red silk slip and cupped and squeezed my breasts, thumbing my nipples, while he pounded away at me in a doggie fuck.

It was both painful and glorious. He was huge and I was taking him, stretched to the limit, but taking him. It was all about him, but there was pleasure left for me aplenty, and if he'd wanted to take me again in the same way after that first time, I would have loved it. I would have begged for it. But there was just that once.

He'd brought his own condom too. Long after I'd come, he pulled out of me, jerked the condom off, turned me and pushed me down in the chair, tore the bodice of the silk slip open, and came on my chest, rubbing his cockhead on the cum he'd spouted on my breasts. He leaned over and cleaned his cum off my chest with his tongue, squeezing what breasts I had with his hands and sucking on my nipples.

When he'd calmed back down, he pulled his jeans back on, grabbed the red high heels off my feet, unlocked the door, and was gone. That was it. He didn't come back. and when I tried to find him on the dating service Web site, he was gone from there too. I could have maybe tried to contact him through the Baltimore Blast organization, but I decided "why bother?" All he'd wanted was a quick fetish fuck in a tight hole and a little play with a gender bender. I had hoped for more and now I'd continue looking for more. I'd just chalk that one up to a connection that failed.

* * * *

"There's a seat free on the exit row, Mr. Wright, if you'd like to have some extra leg room."

"That would be great," Buddy Wright answered. The doors were about to close on the afternoon flight from Denver to Detroit, where Buddy would connect to an evening flight back to Baltimore.

"You called me by name. Terry, is it?" Buddy was squinting at the name tag on the cute Delta steward's chest. He'd already honed in on the young man's extremely narrow waist and hips.

"I know who you are," Terry Harden answered. "You're Buddy Wright, a forward for the Baltimore Blast soccer team. I once played for the Atlanta Silverbacks and I was on the team at the University of Maryland a couple of years after you were a legend there. And not just for your soccer playing."

"Well, fancy that," Buddy said, looking at the trim, young steward with appreciation. "By all means, show me where this seat is that's got more leg room."

The dance between the two hadn't started there, in the plane, as the doors were being closed. Buddy had seen the steward approach the departure gate area in Denver along with other members of the flight crew and he had been struck by the young man's build—a good, firm chest, but his torso tapering down to a very narrow waist and hips. It was enough to make Buddy start to go hard. He'd stared, with lust in his eyes, at the young man, and Terry, sensing the gaze, had looked back and smiled a knowing smile.

The steward told his colleagues he'd be with them in a moment, that he had to go to the men's room. As he turned in that direction, he looked at Buddy and smiled again. Buddy got the message and followed him into the men's room. He saddled up to a urinal beside Terry and looked down—and did a double-take. Terry had unzipped and flared his trousers and pulled his cock out. That's not what caught Buddy's attention, though. Terry was wearing lacy red women's panties. He looked at Buddy, winked, folded his dick back into his pants, and turned and left the men's room.

Buddy had no idea why the other man had shown that he was wearing women's panties, but he went hard.

As they got into the nearly three-hour flight, Terry kept reappearing to give Buddy, now upgraded to the Comfort zone in the plane, the same service those in first class were getting. There was little question he was coming on to Buddy.

When he delivered a beer to Buddy, turning down, in a whisper only heard by Buddy, the passenger's offer to pay for it, Buddy, apparently fully aware he wasn't the celebrity he was getting the celebrity treatment for, asked, "Do you still keep up with all of the soccer arena team players? I'm not exactly at the top of the league in any category." Before Terry answered, though, it hit Buddy that the steward had said he was a legend at the university for more than his soccer ability. He'd had his fetish for narrow-hipped crossdressers even there. It was becoming clear why the steward had shown off that he was wearing women's panties. And it couldn't have been because he knew Buddy would be on the flight, so it must be something Terry already was into. He didn't know what to say next, but Terry had already moved on with why he knew Buddy.