“So, what made you decide to post your ad online tonight?” he asked as we walked down the hall of my apartment building.
“I don’t know,” I replied. “I guess I am just really horny and wanted to try something new.”
I knew, though, why I decided to post the ad that read “28 year old male looking to have sex with a man for the first time. Please, be open to fucking and being fucked.” I have been playing around with anal play since my senior year of high school.
I skipped school one day and decided to check my sister’s room to see if she had any porn. In the back of her closet I found two dildos. Thinking not much of it, I put them back and got on our computer and started searching for porn. I stumbled upon a few sites that featured transsexuals and I felt my cock jump a bit – there was something about these “girls” that had a little something extra. I was enjoying looking at pictures and video clips of the girls getting screwed. But when I came to a video of a guy taking a tranny cock up his ass, my mind wandered back to my sister’s dildos.
I went back to her closet and grabbed them both. She had one long, skinny one and one that was pretty close to the size of my own cock – 6” long and 2” wide. I grabbed some Vaseline from the closet and raced back to the computer. I started the clip again and my cock sprang to life immediately. I grabbed the skinny dildo and coated it with Vaseline. Kneeling in front of the computer, I reached underneath me, spread my ass and put the dildo right at the entrance of my asshole. Slowly, I began to push. Slowly, the long, hard dildo entered my ass.
I loved it! I searched for another video while I rode my first dildo. The longer I went, the easier it slid in and out. I found another clip with a guy with two trannies. One was in his ass and the other in his mouth. I quickly grabbed the other dildo, set it on its wide base on the desk, and started sucking on it like it was the real thing.
The overall sensation was too much. The sound of the guy moaning while he was fucked and sucked; the “girls” telling him to take it like the bitch he was; the skinny dildo sliding in and out of my ass and hitting my prostate; the dildo in my mouth; my hand furiously pumping my cock. I knew I was going to cum. I took my mouth off the dildo, leaned back on the dildo in my ass, and shot the biggest load ever all over my chest. I wiped some of the cum off my chest and tasted it. A bit salty, a different taste than anything else I had tried, but I liked it and swallowed it.
A few weeks later I went to the local porn shop and bought a couple of dildos of varying sizes and occasionally would use them. But was (and still am) primarily attracted to females. Since guys were not really interesting me, I continued to happily date women and, when the mood struck, occasionally use a dildo on myself while masturbating.
When I was 25, I started dating a girl named Cindy. The sex was amazing and we tried many new things. One night we came home from the bar around 2 am and tore each other’s clothes off. We both loved drunk sex. I could last forever and we would try just about anything. On this particular night I was on top of Cindy fucking her hard. She was grabbing my ass, trying to pull my cock in even deeper.
As Cindy adjusted her grip on my ass, I felt her right hand grab my whole cheek and her middle finger touching my hole. Sensing no resistance, Cindy moved her finger tip onto my hole and began rubbing it in circles. Hearing me gasp in pleasure at this sensation she asked, “Do you like that?”
“Uh huh,” was all I muttered.
“How much do you like this?”
“A lot. I love it!”
She then adjusted her grip and began pushing her finger at my hole. Then it went in to the first knuckle. Then she pushed half her finger in me. Then, shifting slightly to her side, she pushed the whole finger in. I was in heaven!
We continued like this for a few minutes. I kept sliding my cock in and out of her, and she kept fingering my ass. “Do you want more?” she asked.
“Oh, God yes! Fuck my ass while I fuck you!”
Cindy reached over to the dresser beside her bed, opened the top drawer and grabbed her vibrator. Cindy’s finger left my ass and was immediately replaced with the vibrator, which she turned on low.
As we continued to fuck each other, Cindy began asking questions.
“How long have you known you like things up your butt?”
“Since I was 18.”
“What have you used up this tight hole before?”
“My fingers. I own a few dildos. Tried the old cucumber once.”
“Since you are so interested in getting me to do a threesome with another girl, would you try one with me and another guy? I would love to watch a guy fuck you like you fuck me. And I would love to be in this position with a guy reaming your asshole instead of my vibrator.”
With that question, she turned up the power on the dildo and pushed the tip right on my prostate. I have never felt better in my life. I started slamming into Cindy with everything I had.
“Yes, yes I would love to fuck you and a guy at the same time! I would love to have a guy fuck my ass while I fuck you! Oh fuck yes! So hot! Fuck! I’m cumming!”
And I shot jet after jet into Cindy.
We tried many different things. She used the vibrator on me many times – both while I was fucking her and also just laying on my back while she jerked me off. And she got me to cum on her tits and lick it off several times. But we never did get to the threesome before the relationship ended.
Which brings me to the ad I placed online. I am now 28, single and living alone in DC. Since I am single and do not know man people in this new city, I end up spending a lot of my time home alone, watching porn. Part of my porn “ritual” is looking at the adult personal ads posted online. As I was viewing those and other pictures of sex acts, I began getting a tingling feeling in my asshole. I was going to need to use one of my dildos to get off tonight.
But I also started to get a little curious and decided to click on a few of the “m4m” ads. And the more I viewed, the more interested I became.
“What the hell,” I thought. “I am horny and there is no girl around. I know I enjoy anal play, maybe I should try the real thing. As long as he understands he will be getting fucked, too. I do have my needs!?”
So, I posted my first ever ad. I immediately began receiving responses. And the first few left me nervous about finding the right guy. They were all in their 50s and overweight. If I was going to let a guy screw my ass, he was at least going to be young and attractive!
And then I found a winner! “Hi, I am 22 years old, a student at Georgetown. I am fit, good looking and looking to have some fun tonight. Let me know if you are still searching.” And the picture he attached was of a young, good looking man. I emailed him and after a few exchanges, he was on his way over.
We got to the fifth floor, walked down the hall and entered my apartment.
“Which way to the bedroom?” he asked. Shocked at hid abruptness, I just pointed. He walked in and I followed. By the time I made my way into my own bedroom, his shirt was off and he was unbuckling his belt.
“What is your name?” I asked.
“Do we really need to exchange names? Its not like we are going to be friends after this. Just take off your clothes.”
He had a point, so I just shrugged my shoulders and began stripping.
“Have you ever been with a guy before?” he asked me.
“No.”
“Then why do you want to?”
“I am just horny. And I have used toys on myself before and liked it, so I thought I would try the real thing.”
The answer seemed to be ok with him as he walked over to me and, without saying a word, dropped to his knees and took my cock in his mouth. My eyes closed and my head rolled back. It had been forever since I had received a blow job and it felt amazing.
He was giving me the best blow job of my life. He was swirling his tongue around, bobbing his head up and down and letting it slide down his throat. I felt his hands parting my ass cheeks and I spread my legs to give him better access. He circled the hole a bit and then pushed his finger in. Then he slipped in a second. He finger fucked me and sucked my cock for about 5 minutes. I felt like was going to cum, but right before I did, he stopped.
He stood up and told me to lay down on my back. I did as I was told. I thought to myself, “If he wants to ride my cock right now, he’s not going to get to enjoy it for very long.”
He climbed on top of me, but he had other ideas than to ride my cock right now as he straddled my chest instead of my waste. His dick was right in front of my mouth now. Since he had been pleasing me, I hadn’t paid attention to how big he was. But now I could see his cock was a little thicker than mine and abut 9” long!
“Open up!” he said. “Its time for you to have your first taste of cock.”
He pushed forward and my mouth opened, accepting the head of his dick. It was softer than I expected as it slid along my tongue. He pushed forward a few inches and then pulled back. I reached up, grabbed his thighs for leverage, and began pulling my head up and down on his cock.
“Oh, fuck yeah,” he moaned. “Suck my cock. That feels so good!”
I kept him in my mouth, drooling all over his cock as I sucked it greedily. I was loving my first taste of cock. I reached one hand up and took his shaft in my hand. I slid my lips off the head, stuck my tongue out and pushed the tip into his pee slit. His cock jumped, but he moaned, obviously enjoying it. I toyed around his slit and he leaned back, reached between my legs, and began fingering my ass again. He then pushed forward and half his cock reentered my mouth.
“You love sucking my cock and having my finger in your ass, don’t you?”
“Mmhmm” was all I could respond with, I couldn’t even take my mouth off of his dick to just say “yes.”
“Good, because you are now going to be my bitch, understood? You will do anything I want, ok?”
“Mmhmm” was again my only response.
He pulled his cock out of my mouth, spun around, and put his ass in my face. When he told me to eat his ass like it was a pussy sitting on my face, I grabbed his ass cheeks, spread them open, and started licking without hesitation. I had licked Cindy’s asshole before and loved it. His was a litter stronger smelling and tasting, but I still loved it.
“You like that taste? I took a shit right before I came over here. I wiped, but didn’t do a very good job of cleaning it up. I wanted to leave that for you. Now clean it real good,” he commanded.
I kept eating his ass and couldn’t get enough of it. I started pushing my tongue inside the hole as it began to open up for me and started rimming the inside of his ring. It was like I was trying to get my tongue up to taste his actual shit, not just the lingering taste of it. I needn’t have worried; I would get to taste the real stuff in due time.
He finally got off of my face. He moved down the bed in between my legs. “Are you finally ready to try a real cock instead of your dildos?”
Oh, God, was I! I was dying to get fucked! He reached down to the floor and grabbed a small packet of lube from his pants pockets. He grabbed my legs and lifted them. I caught on and pulled them to my chest. He spread the lubricant on the length of his cock and placed the head right at my entrance.
“Just to let you know, this is the only time you get lube,” he barked. “After this you will have to do with spit and your body’s natural oils.”
Suddenly, panic set in. I wanted to be fucked – couldn’t wait! – but, “Wait!” I shouted. “We need a condom!”
He just looked me in the eye, smiled, and pushed the head in. As he sat there letting my ass get used to the first cock to penetrate it, he explained that he hated condoms and certainly wouldn’t use one on a bitch like me. Besides, he said, I would love the feeling of his cum hitting the walls of my anal cavity!
After a minute he began working his cock inside of me. Inch by inch I felt my ass being filled. I had never been stretched open this much. I was watching the entire thing, from the moment of penetration to the slow disappearing of his large cock. He would push in, then pull out, and then push back in. Each new thrust pushed his dick another inch farther inside of me. When he was just half way in I thought he couldn’t go any further. But he kept pushing until he had all 9 inches inside of me!
I felt like I was being split in two, and I loved it! He started thrusting the full length of the pole in me now. He would pull out till just the head was in me and then thrust forward. With each passing minute he was moving faster, just as I had done to my previous girlfriends. I was playing with my cock a little, but it felt so good even without that stimulation.
He pulled out of me. I started to protest and tell him I wanted more when he laid down next to me.
“Get on top now” he demanded. “I know you are really my bitch when you do the work yourself!”
I quickly straddled him and reached behind myself for his dick and guided it to my hole. I pushed myself down on it and the whole 9 inches went inside of me. I was possessed now. I wanted him in me as deep as possible. I kept bouncing on his cock for another 10 minutes and I loved every second of it. God, why hadn’t I done this before?
“Fuck me! Fuck my ass! Harder! Deeper! Fuck me deeper!”
He was just smiling, enjoying the fucking. Not as much as I was, but he was enjoying fucking my virgin ass with his 9 inch pole.
“Oh, fuck, I’m going to cum!” he yelled. And I felt jet after jet shoot into my bowels. His cumming made me cum and I shot on his face and chest. I sat their, enjoying his semi-hard cock still in my ass.
“Keep my dick inside you and lean down and lick your cum off of me,” he ordered. I did, just as I used to do to Cindy.
“Good! Now slide off my dick, but hold my cum inside of you, straddle my stomach and drop it there.”
I did as I was told, clenched my ass as soon as his cock had left it, and pushed it out onto his stomach. A big glob landed first and then the rest trickled out. It felt so dirty, so good!
“That’s it, I told you that you would prefer not to have a condom. Now lick it up!”
And I did, sucking up every bit of his cum, his cum that had just been in my ass. And I swallowed it hungrily.
When I finished, I said, “Thanks. That was amazing. Let’s get together again sometime.”
“Bitch!” he snapped back. “We’re not done here yet! Now I want you to…”
To be continued

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