Then Ch. 01

Story Info
He's experimenting in bisexuality.
1.9k words
4.18
37.6k
7

Part 1 of the 4 part series

Updated 10/23/2022
Created 07/10/2008
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I have held a secret for the past twenty or so years that no one that knows me would ever suspect. The reason I am writing them now is because I am having these urges again. You see back then I experimented in gay sex and now I am working hard to get my body back in shape to possibly do it again.

Even though it was over twenty years ago, I can remember it like yesterday. I was just out of School and working as an entry level draftsman at a small company in Dayton, Ohio. The shop was union, and the shop restroom always seemed to have at least a couple of porn magazines in it. I was glad to see the reading material myself. Mostly Playboys or Penthouses, occasionally there would be something like a Hustler or Club or something along that line. Then one Tuesday there was a swinger magazine, Ohio Swingers, in there. I was immediately drawn to it. Here I was, at 20 years of age, looking over ad after ad of women who had placed ads looking to "meet for fun and more." At the time, I wasn't dating regularly, still nursing a broken heart. I wasn't a virgin, but I didn't have a whole lot of experience either. I always seemed to have problems closing the deal. This magazine seemed to be a way to end that. So I took it home to see how to answer a couple of the ads.

In my bedroom, at the time I still lived with my parents, I looked the ads over and over. Masturbating regularly for the rest of the week. Then over the weekend, I decided to answer two ads, one from a 40 year old divorced woman and a 24 year old black woman. I decided that the older woman could give me the experience I was seeking and I choose the other simply because I thought it sounded erotic to me. So I sent replies as instructed and waited.

Two weeks later and many jack off sessions later, I was now looking over the latest version I had bought. I saw the same two ads I had responded to, feeling bad about not hearing anything. Then as I was looking through it again, I happened to look in the men seeking men section. Now I didn't really consider myself bi at that time, even though I had twice sixtynined with a buddy, always very drunk. Still my horniness was getting the better of me. Then I saw the ad. It was the typical black and white picture with a description of what this guy was looking for. The picture, taken in a mirror, showed a naked man holding a ping pong paddle. Even in the picture you could see that he was well endowed. The ad read as following. "Well hung (10") man seeking men (preferred) or women to spank until your ass is red then fuck in the ass. Serious replies only, if you don't like it rough this is not for you."

Try as I might, I couldn't shake that ad. I kept looking at the picture, seeing the paddle and the semi erect penis in it. Never had I seen such a large one outside of a porno. I had never even considered anal sex before, not even me screwing someone else in the ass. Still here I was masturbating daily thinking about it. Finally, my curiosity got the better of me, and I answered it along with one to another woman. Five days later, I got a phone call. He introduced himself a Jim and that I had replied to an ad he had placed. Nervous, I said yeah that was me and we made plans to meet half way between us, at a mall, that weekend.

We met near the food court, I asked him if he wanted anything, his reply stunned me. "My ad told you what I want." My cock was immediately hard. Then he asked me about my experience, how many men had I been with. When I told him he only smiled. "Oh this is going to be good. You sure you want to go through with this? Because I will drive us to my house and once there, your ass is mine, got it." His forcefulness was really turning me on. I told him I wanted to. "Tell me want you want." Looking around, seeing a lot of people around I hesitated. He leaned back in his chair. "Either tell me want you want, or I walk."

Embarrassed, I spoke softly, my voice cracking, "I want to be spanked and to have sex with you."

"Louder!", he insisted.

So I said it again, twice, and he smiled. The he got up and nodded to me come along.

When we were in his car he drove towards the exit of the parking lot, then when we were away to most of the cars he stopped and looked around. "Okay it's a ten minute drive. Here is your last chance to back out." With that he slipped his shorts off. "Other wise I expect to you to get me hard by the time I pull in my garage."

I could only stare at his manhood. Not even erect and it was bigger than mine. I remember licking my lips and reaching over to touch it. As I began to feel him up, he drove on. "Your mouth will work much better." And he reached over to pull my head down. Submissively I allowed him to do it, feeling completely horny. I opened my mouth to take him in. His head was massive and barely fit in. "So I take it your friend wasn't this big." I raised slightly to say no, then I went back to work on him. Then he placed his hand on the back of my head, with his cock head just behind my teeth. He pushed my head down on his manhood, trapping me with the steering wheel. Suddenly it moved, sliding deeper into my mouth. I tried to raise up feeling a sort of panic as he continued to swell in my mouth stretching it. Soon his head was in the back of my throat, and I still didn't have it all in. The he relaxed his grip and I was able moved up, then he pushed me back down. This went on for what seemed like forever, my eyes teared as he continued to gag me with his manhood, and my head banging the steering wheel.

"Good job, kid, were here." I looked up to see his garage door rising. Taking a quick look around I saw that he live well out in the country.

"Okay, take everything off, except maybe your shoes and leave them in here.", he said as he got out of the car. Quickly I stripped my shirt and jeans and we entered his house.

Once inside he gave me a once over. Touching my cock he added, "Not bad, what about 7 inches?" Nodded yes. "Okay then, lets get to work"

He led me into an extra bedroom with no furniture, just some boxes stacked along one wall. I remember the curtains being open and asking if we should close them, only to be asked why. Then I was instructed to bend over and grab my ankles. When I did he began to spank my right cheek with his hand, then he would rub it. This went on several minutes, then he switched sides. My cheeks were already warm and he told me they were getting nice and red. Then he had me move over to a wall and place my hands on it. With that he kicked my legs back and spread them out. I thought this is it, I'm about to get fucked. But no, Jim grabbed that paddle from the ad and began to work my ass over. He was an expert, he would paddle me, then console me. All the while telling how he was going to fuck me like a little bitch. Unbelievably I was getting more and more turned on. Soon my checks were on fire and tears ran down my face. Then he began to finger my ass and paddle me. Later I realized he was lubing me up. As he fingers felt cool and after he first worked on in, soon he was sliding three in. Then he stopped fingering me and began to paddle me hard, asking me to beg for it. My cock was still hard, my face wet with tears, and my ass felt like it was literally on fire.

"Please, stop, please."

Whack "thats not what I want to hear" Whack, Whack, Whack.

"Please" Whack, Whack. "Please, fuck me." Whack.

"Thats better", Whack, Whack.

Soon I was screaming it, "Fuck me, Fuck me." Then He split my reddened ass as I stood there. Grabbing my left hip, he slid his head into my anus, causing new pain.

"Your choice, this", as he slid it slightly in further, "or more spanking" Then he slid a little farther in. I screamed. Then he smacked my ass. "Which is it?" as he continued to smack my ass and slid in deeper.

"Please, fuck me." I felt tremendous pain as he entered me. Soon the horrible pain eased as he stopped spanking me and had most of his penis in my ass. He held in there for a minute. Then he withdrew almost completely, before driving completely into me. Soon pain turned to pleasure as he stroked in and out of me. With each long stroke, my hurting cheeks smacked his hips and I could feel his balls slapping mine. Like everything else about him, him fucked me forcefully. Each time the was a loud smack as he bottomed out. Then he reached around to stroke me. I came almost immediately, shooting my load on the wall, as he continued to drive into me. Then with a loud grunt, He exploded inside my ass. He still gave my asshole a few more strokes before withdrawing. When he did, I fell to my knees, my face against my load on the wall completely spent. My legs felt like rubber and I noticed the wall was stained with the cum of others.

Afterwards, we showered. In the bath room I looked at my ass, it was cherry red and I had to walk like I had been horse back riding. Which, in a way I guess I was. He took me again in the shower, then he blew me. I can still remember how great that felt.Then he drove me back to the mall and we said our goodbyes. As I was about to leave, I ran into a woman I had dated previously. We decided to go out the next night, and I ended my drought with women that night. Still, I kept thinking about Jim. I ended up seeing him and Michelle, the woman, regularly over the summer. Each time with Jim was similar to the first. Over the summer we met about 5 or 6 times, roughly every two weeks. By the end he taught me how the deep throat him and swallow his load before our usual session. But by the end of the summer, it ended as Michelle and I became more serious. However I never stopped thinking about what I called my other side.

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5 Comments
AnonymousAnonymous7 months ago

"He took me again in the shower,"

I have read this story several times, and that line always makes me hard. I loved this story the first time I read it and it make me so hard.

t1m1d1t1m1d1almost 11 years ago
dreamy

loved this story , oh to be spanked and then dominated by that huge cock! i was hard through most of this story

AnonymousAnonymousalmost 13 years ago
Hot, hot

This is the hottest story!

When I first read it, I was so fucking hard! I have never done spanking before, but being put up against a wall and spanked and then fucked got me hard.

AnonymousAnonymousabout 13 years ago
barebacking

Iloved your story. Especially when the dom fucked your ass and exploded inside you. I really enjoy the feel of hot sperm leaking out of me after i have been royaly fucked in the ass mmm

AnonymousAnonymousover 15 years ago
Why I can not vote?

Was Ok

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