Category: Anal Stories

A First Time for Anal Play Ch. 5

by BigMan©

The days went by slowly till finally it was the day for Julie's party. I was so ready. I had only seen her once, she didn't hang out at the pool very often it seemed. I would have noticed her long before if she had. I finished work, and went home to masturbate as I had a few hours till I had to leave. I booted up the computer when I got home, did a search, and downloaded some movies. Dick in hand, I was happy spanking the monkey till there was a knock on the door.

Pulling on some boxers, I went to answer it. I asked who it was, and Brad hollered back through the door for me to let him in. My dick tingled. I had an ass ready for fucking right outside my door.

Ever since I had let a man fuck my tender asshole, I had had a few nagging worries about being gay. Brad had sucked me off once and I had then fucked him, but that was just for relief. Even though Brad and I had repeated several times, I never had any doubts about my sexuality. Having another mans cock up my rectum had changed all that. I had enjoyed it. Twice!! And now here was Brad, and I was horny and I knew I would be shoving my pipe up his back passage in short order. Was I BI??? Shit, I decided to let him in.

We talked a bit and explained what had happened a few weeks ago with Ethyl and Mark. I explained my confusion, and Brad was quick to help me out. He pointed out that I really didn't like men, and if given a choice there would never even be a real choice, I was a straight man who occasionally let my need send me down an alternative place. I had no reason to worry.

I told him about Julie and the fact that I was in love with someone who I had only met for 10 minutes. Me, who never really wanted any commitment, just fun, and I was nuts over a woman old enough to be my mom. We laughed about it, and I told him about how she looked and smelled, and how one touch had made me weak. As I talked, my prick rose. Pretty soon it was obvious, and I looked at Brad and asked him if he wanted to do me a favor. He laughed, and jerked out his dick and began pumping it. I followed suit and soon he was on his knees between my legs.

Before too long, I stopped him and asked him to fuck me. He just looked up at me, his mouth open. I told him I had really liked the feeling, and felt safe with him, and damn it I wanted something up my ass as I came... I just sat there waiting, and finally he blinked his eyes and asked if I was sure, and I said yes. Somehow, I didn't want to do it in the bedroom, or even the couch. It seemed to intimate. I stood up, jerked my boxers down around my feet, stepped out of them and went and leaned against the wall, my butt out. Brad seemed to understand, reached in his pockets, got a condom, dropped his pants, and started toward me. My dick was straining upward ready for action, but it was my butt that would receive it.

Condom on, he turned and went toward the bedroom, I hollered out where the lube was and he returned. Lubed, he got behind me, and I had to bend my knees a bit to give him access to getting his short fat wang totally up inside my ass. Quickly he was inside me, pushing apart my sphincter in an effort to get his dick to impale me fully. In short order he did. As he reamed my ass, he reached around for my dick and gave me a pretty good hand job. I came pretty quickly. He continued pumping my ass, and fondling my balls and prick. I was soon ready for round two. He pounded his meat into me, and I was able to concentrate more on the feel of his tube sliding up and inside of me. I still liked it. It felt so dirty, but was so hot at the same time. I loved the feeling of the movement inside my ass.

Suddenly he stopped, grabbed his pants, got another condom and asked me to put it on. He re-entered my butt and was now slowly sliding his meat in and out of my rectum as I tried to put the skin on. When I had gotten it on, he pushed his entire pole hard inside me, his balls up against me, and he leaned over and asked if I would fuck him so he could cum. No problem. He slowly pulled his dick out of my stretched open butthole, and I pushed him against the wall, and got behind him and lined up my dick with his ass ring. Without much ado, I was inside and pumping my penis through the walls of his ass. He had one hand supporting him on the wall, and the other was fisting his cock I guess, cause all of a sudden, he reached around, pulled me close, and then started to cum. I pulled out a bit, and then slammed into him hard, lodged all the way up his butt as he finished cumming.

We cleaned up, and I had to move a rolling book cart over the wall to cover the stains our cum had made. Oh well. He left shortly, and I thanked him and told him not to expect that again. He said he understood and left. I showered, put on my swim trunks, and a tight white shirt, and headed for Julie's.

I got there, and the house seemed empty. If it weren't for all the cars in the huge curved driveway, and off to the side, I wouldn't have known there was a party. It was just getting dark, and I was led around to the pool area. There was no one back there. The girl who had let me in explained that they were all watching a movie. She asked if I wanted anything to drink, and I opted for some iced tea. After all I was working. I roamed the pool area and checked out the equipment. There was a path leading down from the pool through some hedges, and there were three tents, the kind with no sides, just a top. Beside each tent was a small dresser, and under the tents were couches, huge chairs, and pillows everywhere on the huge furry rugs that covered the grass.

Oh man, looked like some funky stuff was gonna happen here. Annette, the girl who had let me in came down the path with my tea. She explained that the husband was a porn film mogul, and they were in watching his newest release. A lot of the visitors were money guys, who they wanted to invest in the next movie, so this was a way to sway and impress them.

Whatever. We trudged back up the hill to the pool, and I could see people milling around inside. I headed for the platform chair at the deep end. It took awhile for people to filter out. Mostly they stood around and talked. I still hadn't seen Julie. Thankfully with no on in the pool, I could look inside and focus on finding her. Finally I saw her. God she looked Incredible. She had on white pants that were tight and ended around her calves. She had on a pale pink sleeveless shirt that tied above the waist showing a little skin. She was talking to one of the servers. She disappeared through the door again for awhile, and then was back. I followed her with my eyes as she moved around talking to different people.

Finally the pool was getting customers, and I had to quit watching her. Pretty soon, there was some hanky-panky happening. One old fat guy was obviously porking a tall young girl over the edge of the pool. He was sending tidal waves with his thrusting movements. One young girl was bobbing under the water for a few, and then coming up for air and then heading back down. Several of the younger girls were now walking and swimming nude. There was lots of groping and rubbing, and eventually there was a girl on her knees blowing one of the middle-aged guys. Shortly thereafter some of the loungers were used as fucking racks.

A lot of people were filing out down the path. The pool stayed busy even though most everyone had left for the fuck tents. Finally Julie came out. She headed my way, and had a glass of tea with her. She thanked me for coming, and was glad I could do my job without being taken aback at the goings on. We chatted a bit and she told me about her husband and his job, and it was clear to see she hated it. We chatted a few more minutes, and there was an announcement for all guests to please come to the reception area. Julie excused herself, and headed down the path. One of the young naked girls stayed, and headed to me. I got a great blowjob, and she left. Afterwards, I wandered down the path and looked out over the tents to see what was happening. Julies husband was talking to the people who were lying sitting and fucking and sucking in the tents. I watched the action awhile and headed back to the pool. Shortly, another girl arrived, and I got to impale her wet pussy with my big stick. Whatever was happening in the tents finally broke up, and some guests headed back up. There was lots more drinking and fucking and sucking, and then it was over with no incidents. Julie came back out after all the guests were gone and wrote me a check for a lot more than we had discussed.

She sat there for a while and we talked for about an hour. I got her background and that this was an unhappy marriage. She had been recovering from her first divorce when they met; he was rich and handsome and paid her lots of attention. She married him as soon as the divorce came through. Eventually they saw little of each other; she was nothing more than a glorified hostess. He had sex with everyone who came in the house it seemed except her. She actually said that she didn't care about that, but hated feeling as if she were essentially worthless.

I asked her if she had ever strayed and she said no. She had considered divorcing him, but didn't want to go through all that again, plus she had no idea what she would have and how she would live if they split. He was a pretty ruthless guy evidently. I told her that she should really get away from him and get back into living. I told her how beautiful she was and even though I respected it, I was sorry to hear that she didn't cheat. I explained to her that I found her sexier than any other woman I had met and was extremely attracted to her. She laughed, but it was soft. She said she was sorry too. Now I was really in love. All the way home I could smell her and hear her voice and feel the touch of her hand on my arm.

Evidently the girls I had fucked had talked to Kit, the husband, and several days later he showed at the club. We talked and he offered me a gig in one of his movies. The girls had liked the equipment I had and how I used it, and he said I was filmable. I wanted to think about it, and we met later. I agreed to do it. Partly it was in the hope that I could somehow see Julie. I did once at their house, but it was just to nod hello. Now I felt like a heel. I was doing what she hated. But the money was pretty good and I liked the idea.

Kit was getting a decked out RV and we were going to shoot as we traveled. Hopefully we could pick up some new flesh as we went. I had a porn film that had some of the same type of action and it was hot. I liked the thought of fucking a girl in the big front window for horny truckers and pretty women to see. I liked the idea of my dick immortalized on film.

I quit my job at the club and had great coupla weeks getting all the ass I could from my lovely ladies. They were sorry to see me go, and I was sorry to lose the income. We set out with me another guy, two ladies and two camera guys and Kit. It was a huge, plush RV. We went over the shooting for the next day, as we rolled down the road. We headed down from LA to San Diego. We arrived in San Diego and got a decent hotel. The other guy, Mack and the two girls Wendy and Pam and I were to stay together in a suite and get to know each other. Wendy was the one I had fucked at the party, and she opted to stay in my room.

We got to business pretty quick. As I lay back, she was between my legs coaxing my monster to life. She was really good. She could deep throat and I shot off in no time. Soon I was on top, entering her willing pussy. We got off pretty good, and slept for a while. When I woke up a little later, I heard sounds from the bathroom. I went in to check it out. She was in the oversized tub, a line in her hand that led to a bag hung off the shower curtain. I sat on the toilet and got the low down. She was giving herself an enema. She knew there would be anal sex, and she preferred to be clean, so that she could suck dick afterwards without being revolted.

I watched as she lay on her side and she asked if I would put the nozzle in her butt. Mr. Happy woke up, and I was getting a hardon as I slid this thing into her ass hole. She thumbed something on the line, and I could see liquid going down and into her butt. She lay there awhile, and the bag was now pretty empty. She closed the line and asked me to leave. I asked why, and she said it could get pretty gross, that later I could watch. I left, but left the door open so I could see her in the mirror pretty much. She was right it was gross. I left. Awhile later she said to come back in, and I helped again insert the nozzle in her ass. This time I climbed in with her and sat near her head. She lifted it, and I slid my thigh under her head. I took my dick and waved it at her and she started sucking me off as the enema flowed into her.

When it was done, I was rock hard and nearing cum point. She let go of my dick and asked me to fuck her. With all the stuff in her I asked???? And what happens if she leaks??? She told me to go slow and easy, and that the water was clean, a lot cleaner than my dick coming out of an ass was, and it would be warm and different. I was game, so I knelt in the tub and lifted a leg. I guided my hardon into her pussy and gently shoved my rod in. Her stomach wobbled around as I easily slid in and out of her. I really couldn't tell too much difference. Then she said, "here it comes" and I could feel the water coursing through her rectum and then I was bathed in warm water. She came. I began to poke at her harder and in no time, I was coming in her as little jets of water squirted out with the last of my thrusts. Wow.

We showered and dried off somewhat and hit the bed. My prick was following the route of that nozzle, and soon I was fucking her cleaned out bowels, her ass gripping me as I fucked us both to another orgasm. It was so hot. It didn't take much time for me to get ready again, and I was back in her sweet ass, now dirty and coated inside with my cum. I lasted a long time, and she didn't seem to have a problem with that. Her hand was on her clit constantly, and one time she asked me to get a vibrator out of her back, and she fucked her cunt with it while I plundered her ass. Man, I love watching my dick swallowed by an asshole.

We woke around noon and got something to eat. Mack, Pam, Kit and the 2 camera guys (Dan and Bill) drifted in here and there. We shoved off in the RV around 3:00 and listened to Kit describe some of the things he wanted as we rode down the highway. The passenger seat up front was big and swiveled and the dash in front of it was deep. Deep enough to sit on, so there could be lots of eating and sucking of various genitals. The girls would be able to lean over and stick out their butts with their faces only moderately crammed against the glass.

Behind the seat was the salon area, a big huge window that had a low round table and two swivel seats on either side. Perfect for fucking and sucking and giving a great view to the driving public. We got naked and Joe (the driver) stayed in the right hand lane as we tried out various positions and Kit got the camera angles he wanted. It was a bit nerve racking having a one of the girls suck you and then have to knock it off when he got the right angle. Then we would get set up and switch so that there was some fucking going on. Our butts towards the window, then on the table our genitals facing the opening, then in the chairs, fucking and then pulling out and standing around, it was maddening.

Finally we were ready to start filming. It was dark now, and there was a rig behind us. Joe pulled over into the left lane and slowed down a bit so the rig would begin to pass us. I was sitting up front on the dash pulling my meat, and Wendy was sitting in the chair her tits facing the window as the guy in the rig pulled even. He got a good look at Wendy and matched speed with us to gawk at her. I don't think he even saw me. Wendy pulled on her nipples and lifted her tits up to lick at them. The guy was honking and Dan was filming. There was a monitor positioned that I could see, and it showed Wendy's tits as she worked them and the front of the rig. Then Wendy turned and went down on my totally hard member. We speeded up a bit and so did the trucker. We slowed and so did he. After a bit, Wendy got up and she headed for the back. I was left there my dick waving in the air, and finally followed her back. The trucker finally pulled away.

Pam and Mack were in the back bedroom area getting some 69. They headed up front and did their thing and caught another trucker to watch. I had a serious case of blue balls and headed for Wendy and dragged her back to the bedroom area. I pushed her on the bed and opened her thighs and shoved my stick in. I fucked her hard and came pretty quickly. Relief...

We spent the night fucking on the table in front of gawking drivers, it was great. I finally got inside Wendy's ass; we were sideways to the window, my pole visible to the driver as I slid it in and out. That was my last cum for the night. We pulled over eventually and hit the sheets. Wendy slept curled into me and I was too exhausted to even care. Next morning, we hit a beach, I have no idea where we were, and pulled the RV onto the sand.

More fucking and sucking to gawkers who wandered the beach. Joe was outside kinda screening the people who came up. It was a turn on to fuck to an audience. There was a mother daughter pair who spent some time talking to Joe and then he got Kit and he talked to them. They wanted to join in. Kit did some paperwork stuff and they came on board. I got the daughter. She was around 20 and in pretty good shape. Long brown hair, green eyes and decent sized tits. We talked a moment and then Kit was there to set up the shot. She got on all fours on the table, sidewise, and I put one knee on the table, and rubbed my engorged member up and down her slit. I slid into a tight and wet pussy. She was a serious moaner. It was pretty exciting. There were 4 guys outside the window all rubbing their crotches as I fucked in and out of her. The girl came and I was still holding out for more.

After a few minutes, she asked if I would fuck her ass. She said she had never done it, but it had turned her on when she saw my pole working in Wendy's ass. Kit had me lie on the table, my wang sticking up, Pam came by and began to give me head as they got the girl ready for her first anal intrusion. The girl knelt ass out in a chair as Wendy took a tube of lube and worked her fingers in and out of the girls butt. Then she took a medium sized butt plug and began to go to work on the girls virgin ass. By now the guys on the beach had their dicks out and were all jerking off. Finally Wendy decided she was ready, and Pam left her job of keeping me ready. The girl stood in front of the window and straddled my knees. Finally she started to squat. I held my dick poised and ready for a virgin ass.

She slid down and engulfed my prick with her pussy. After a minute, she slid back up and this time lowered her little rosebud of an asshole till it was touching my cockhead. I gripped my dick hard behind the head as she pushed down and tried to get her asshole to open. I watched part of my head disappear, and then it slipped up. We tried again. I heard her mom cum on Mack's dick, and I was desperate to get inside this girls butt. We lined up again and she began pushing down as finally the head of my dick slid in.

Oh my God she was so fucking tight. She sat there going no lower, just rotating on my knob. My god she was so tight that I though my head was gonna pop off in her butt. Finally I couldn't stand it and shoved up and got about and inch in. She screamed. Later, I saw the shots of that, and one of the guys on the beach emptied his load on the sand when she screamed. The girl tried to stand up, but Wendy kept her pushed down, and I grabbed her hips so she couldn't get away. She was moaning, and I pulled back and pushed back in softly a few times.

Category: Anal Stories