A gay story: The Ride of a Lifetime It was the day after my 21st birthday, I was finally old enough to drink! It was early in the evening, so I decided to walk down a few blocks to a neighborhood bar. It was pretty quiet inside as I sat and ordered a beer. An older man was sitting just down from me, and I noticed he was eyeing me. He wasn’t in bad shape, probably in his late 40’s with a goatee, brown eyes and a sturdy figure. After a few minutes, he came down started talking to me. He was friendly enough I found him quite interesting. At some point we were discussing hobbies and he mentioned robots- specifically how he liked to make them. He was an engineer and seemed to specialize in all kinds of advanced machines.
By now I had had 4 beers (he insisted on buying the last 2) and was feeling kind of drunk. Suddenly, he asked if I would like to come over to his house and see some of his work. Normally I would have been more cautious but the alcohol has loosened my inhibitions. I agreed to go, stopping only to pee before we left.
His home was a relatively short walk from the bar, and it seemed quite big. He led me into his workshop at the back of the house before handing me another beer. I began to examine some of his handiwork and was quite impressed! He hadn’t been bragging about his skills.
Out of the blue, he asked me about my sex life. That sort of jolted me and I slowly answered “Sure, but…”
He laughed. “I’m not asking you if you wanted to have sex with me, I’m a lot older than you are.”
I felt relieved. Truth be told, I had never been approached about sex (neither had I had much experience), so I didn’t know what to say.
He then astonished me by asking “Would you like to go for a ride on a machine?”
“Ride? What kind of machine?”
“A sex machine.”
I couldn’t believe it. I knew about vibrators and small toys, but an actual machine?
“Come, I’ll show you,” he said. My curiosity, mingled with my slight arousal at the mention of sex, got the better of me. I followed him into a smaller room at the back that I hadn’t noticed before. It was very dimly lit, with light background music playing. In the center of the room was what resembled a large massage table with a small bed on it.
He said, “Take off your clothes and put them on the chair over there.”
I hesitated. Sure, I’d had a good time with this man so far, but could I trust him?
“I don’t know about this…”
“Nonsense, you’ll enjoy this and it will feel real good. It’ll be like nothing you’ve tried before.” I knew I had had too much to drink as I found my self-undressing. I walked back to the table and he demanded, “The underwear too!”
“But I-”
“Don’t be shy, it’s just us.” So I slid my underwear off and found myself completely naked. I felt embarrassed standing in front of him, but luckily the lights were dim. Nobody else had seen me naked except the family doctor and the high school football team when we took our showers. I was wondering what he would say if he saw my hard cock, since it was over 7 inches long. Although I was nervous, I was also getting aroused.
He told me to get up onto the bed and lie with my head on the pillow. I don’t know why I felt compelled to do what he said, but I obeyed. The bed was designed so that my upper body lay comfortably on it while the lower part sort of dangled off. I assumed he would remedy that. The part I was resting on was soft and comfortable, making me feel drowsy and comfortable. My cock grew harder.
Then told me to spread my arms and legs out a bit more so that I was at a spread-eagle. I did so, unassuming, as he came near the head of the table. I didn’t know what he was doing until he pulled out some soft, padded Velcro cuffs that I hadn’t seen before. They were attached to the bed and before I knew it, both my wrists were bound securely.
“Hey!” I half-heartedly protested.
He shushed me, telling me it was just part of the machine. I didn’t want to admit it, but this twist was beginning to turn me on even more.
He came down to where my legs were and pulled out two padded leg rests for my lower body. Putting my legs on each, he secured me to them with two more of the same Velcro cuffs around my ankles. Now I was completely helpless and starting to feel scared.
He reached under the table to adjust some knobs and the next thing I knew, my legs were raised up in the air, bound and spread. I got even more scared.
“You’re not going to…”
“What? Fuck you? No, I won’t be doing the fucking.” He chuckled and went to behind my head where I heard him fiddling with some equipment.
I was completely under his control, trapped and unable to move.
He flipped a switch on the wall and a small spot light came on, shinning down from the ceiling on my cock, balls and my ass. Oh God! It was like almost like a small stage light which illuminated my privates and my ass!
Then he reached down between my spread legs and brought some kind of mechanical arm up from under the table. I tried to raise my head to see what he was doing. The arm looked like it had been modeled after a human elbow joint, able to go back and forth in a thrusting motion. Attached to its end was a medium-size, thick dildo. He spent some time adjusting it and coating it with what I assumed was lube, until I could feel him pushing right against my asshole. I started to make a noise to object, when he suddenly came up to the head of the table and popped a rubber ball gag in my mouth! He lifted by head as he tied it and then let it drop back on the pillow.
Damn! What was I to do? I could only make small groans now, no matter what I tried. He leered at me and said he’d remove the gag after I’d tried the machine for a while. I needn’t have worried about having my asshole torn though. He turned the machine on and the dildo began to tap slowly against me. It didn’t actually go inside, but just kept bumping against the entrance, like it wanted in. I had never thought of my ass as an erotic spot, but this was making me reconsider. He adjusted the speed, making it go a bit faster. Tap. Tap. Tap. Oh, it made my ass feel funny.
The man approached the side of the table and reached up toward the ceiling, bringing down another mechanical arm. This one he positioned near my cock. It had a sort of cylinder, unlike the one with the dildo. He opened the cylinder and I could see it had some kind of foam lining inside it. He put some kind of massage oil all over my cock. It was soft because I was still kind of scared. Next he placed the cylinder around my cock and closed it so my cock was trapped inside. I noticed the cylinder was open at both ends. He made some more adjustments to it.
Then he took a small leather pouch and forced my balls inside of the pouch. He then tightened the strings on the pouch so my balls could not escape. A small string from the bottom of the pouch was attached to the arm. He made a final adjustment to the arm from the ceiling and turned it on. It pushed down to the bottom until it was touching my crotch, then it slowly went up until my cock head disappeared inside. Then it started down again.
Every time the arm pulled up, the pouch with my balls inside went up as well, pulling my balls with it. It was not painful but very erotic. He’d tied them in the spot that could get maximum stimulation. Ohhhhhhh. Then it went back down. Ahhhhhhh.
He adjusted the speed until it was going faster and faster. My cock swelled and grew as hard as it could get. It was so tight inside the cylinder, in fact it felt like it was tightening and releasing each time my cock was inside. I was moaning uncontrollably now. With each stroke my cock head would disappear inside the cylinder and then on the down stroke my cock head would fully appear outside again. My cock head is especially sensitive and this kind of stimulation was driving me crazy as it kept me just on the edge. It was feeling so good; I had never felt anything like this while masturbating.
He slowed the cock machine considerably and then went between my legs, adjusted the dildo so it was entering my asshole just a little. I felt myself squirming against my restraints. When he restarted it he made it very slow. In, out, in, out, in, out. The machine was starting to slowly fuck me. Ohhhhhhh. My asshole had become looser because of the constant tapping from earlier and all I felt was unbelievable pleasure as it opened me up.
The man came to the side of the table and poured the same massage oil on my chest and tummy; then he started to rub me. His hands were strong and skilled; whenever he reached my nipples he would pinch them. He was pinching and squeezing them as the machine was milking me slowly, tugging on my balls and fucking me. Ohhhhh damn. All I could do was moan uncontrollably as I felt unbelievable pleasure coursing through me.
He went back between my legs. Oh no!!! He adjusted the dildo so it was going to go all the way inside. The dildo was curved slightly upward so when it thrust in I could feel it hit my prostate. I was told once that if someone massaged your prostate you had no choice but to cum, but there was no time to think about that. He started the machine up and the dildo was going in and out, in and out, each time hitting that sensitive spot inside of me. He sped up the machine milking my cock as well. Ohhhhhhhhhh, this was too much! I needed to cum so bad!
He chuckled as he heard my continuous moans, pausing to pull the ball gag out. I think he knew I wouldn’t tell him to stop at this point!
I discovered that he had some kind of foot pedal on the floor so he could adjust the speed with his foot, while he massaged my stomach and chest and pinched my nipples. I moaned even louder when he pinched my nipples.
“Oh, you like that?”
Then he left and returned with two clothespins. He snapped one clothespin on my right nipple and one on my left. I squealed as he did so, my wrists tugging ineffectually against their restraints. They were very comfortable and didn’t cause me any discomfort despite my chafing. It was so erotic, especially since I was completely helpless. Now my nipples were feeling so sensitive, as though there was a mild current passing through them. I had to close my eyes and let my head fall back, panting so that the rush through my head could pass.
When I opened them, it was like rediscovering my whole situation again. Here I was, helpless, with my legs wishboned up and out and being stimulated all over my body. This was an unexpected birthday present to top all others!
Suddenly I felt myself building up, my cock getting even harder and I knew I was going to lose it and shoot. The older man was playing with the clothespins on my nipples, flicking them back and forth. He sped up the milking machine even more. Oh, my balls were bouncing back and forth hard now.
Suddenly he slowed both machines down again, having built me up to an agonizing peak. He said, “No, you can’t cum yet!”
I think he knew I was about to beg him to let me cum, so he simply picked the ball gag up again and shoved it back into my mouth.
Now all I could do was moan and let him have his way with me. This went on for a long time, faster then slower, somehow he knew exactly when I was getting ready to cum and then he would stop it. It’s a good thing he’d gagged me or I’d have screamed myself hoarse, begging him to let me cum. I felt like I was on the brink of insanity with the feelings that were coursing through my body. My body was dripping with sweat and I was wound up beyond belief! I had moaned enough for a lifetime too!
He looked me in the eye and asked if I really was ready to cum. I nodded as best I could with the gag and he pulled it out, telling me not to beg or it would go back in. The machine fucking my ass sped up first, soon going very fast. Then he sped the machine milking my cock as well. Oh my God, ohhhhhhhhhh, Oh my God! He finished by going between my spread legs where the machines were doing their work. Once there, took two oily fingers and pressed them up against the sides of my perineum (this is the line between a guys ass and balls, it is incredibly sensitive). With both fingers, he began a firm massage, coinciding with the moment the milking machine gave my cock an extra tight squeeze and my prostate got stroked yet again by the dildo.
I exploded with a yell, my body shaking with the force of the orgasm, pulling inward, and straining against the straps that spread me wide. If I hadn’t been restrained, I think I might have fallen off the table. I shot volley after volley of cum out of my cock, high into the air. It came splashing down on my chest and tummy. The machines were still working me hard and without warning I exploded a second time, this time barely able to groan. All this time he continued with the his perineum massage until I was completely drained.
I closed my eyes and lay my head back down on the pillow, my mind seeing distorted, blurry shapes and colors. I knew I had had a full body orgasm, the most intense sexual experience of my life. I was so tired; all I could think of was sleep, even tough I was completely covered in my own cum and soaked with sweat.
The man slowed the milking machine down to very slow speed, and turned off the machine fucking me, but he left the dildo all the way inside me. My cock was hypersensitive and even the tiny bit of stimulation caused me to try and buck away- useless since I couldn’t move. He got a warm, wet towel and wiped off my chest and tummy. He also took off the clothespins, which made me groan and wince as the blood rushed back into my nipples. He said, “Good boy, you sure had a lot of cum saved up.” I kept my eyes closed and did not answer him. I just wanted to go home and sleep.
Instead, he started walking out the door, saying, “I will be back in a little while.”
“No, stop! Turn this machine off and let me out of this!”
But, he was gone and didn’t hear me. The machine kept rubbing my cock very slowly up and down. My cockhead was so sensitive that when it disappeared inside the cylinder I would moan loudly. After a while it got so sensitive I started yelling, “Stop this thing!”
He didn’t come back, so I had no choice but to get used to it.
I fell asleep for a few minutes, but awoke when I heard him walk back. He laughed and slapped my bare ass, causing me to jerk erratically in the restraints. “You forgot to turn the machine off!” I complained.
He smiled and said, “No, I didn’t, I wanted to keep your cock hard. And I can see it’s still as hard as a rock.”
Then, moving down between my legs again, he asked “Well, are you ready to do that again?”
I figured he must be joking, let out a weak laugh and asked “I think I’m pretty much done for tonight, I should go.”
Now he laughed and said, “Oh, no, we just got started.”
“What?!”
I think I knew where this was going and I couldn’t imagine going through all of that again!
But before I could say more I found the ball gag back in my mouth. This time he also put a blindfold on so I couldn’t tell what he was doing- which just made it more erotic!
Then he sped the milking machine up faster and went and turned the dildo machine back on so it was fucking me again. My aching cock started to feel really good again. My balls were being tugged on again.
Laughing, I heard him say “We’re going to drain ALL of the cum out of you before you leave.”
All I could do was moan and let it happen.
“All of my boys cum several times before they leave.”
Huh? His boys?
As if sensing what I wondering (for the short time I could still think coherently), he said, “Yes I have 12 boys in my stable, you are number 13. When you leave here, you are going to swear to yourself that you will never come back. Then in about 2 weeks, you will call me on the phone and ask if you can come and see me again. All the boys do that.”
The old man was chuckling to himself as he used his hands, covered with massage oil, to pinch my nipples again.
Damn, deep down inside, I knew he was probably right. I probably would be back.
And then he sped the milking machine up faster.
Moannnn…