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Wally and his assistant Annie were having lunch on a Friday afternoon before a long weekend. Since they had Monday off, he had given the rest of the staff permission to leave early. It was not only being generous and considerate but it allowed he and Annie to be alone in the office later that day. The two of them loved to have sex in the office and they always took advantage of being alone.

The lunch conversation had turned toward sex which was not unusual for them. However, Annie surprised him by asking about his anal experiences. Wally agreed to tell her if she would also share her story with him. They agreed and ordered another glass of wine. They were in no hurry to get through lunch as they had all afternoon with each other. Wally began his story.

WALLY'S STORY

It was when I was in Catholic School at a small private college. We all wore uniforms to class. I was dating this very cute blonde, Jane, who had gorgeous legs and a killer ass. She was small breasted but as you know that is not important to me. In fact, you could say she was flat chested. The girl's uniforms turned me on as the pleated skirts were short and every so often I would get a glimpse of a girl's panties. 

The uniform for the girls was a pleated plaid skirt, light blue blouse with a string tie, navy blue blazer, white socks that came up to the knees and saddle shoes. For the guys we wore gray slacks, white shirt, a blue striped tie and a blue blazer. It was difficult to get through the day without getting a boner at school. Jane was not a virgin when we began dating but so far it had only been vaginal sex with her.

My favorite position was with her on all fours, her skirt tossed over her back and her panties pulled down to her knees. I would kneel behind her with my pants and underwear pushed down to my knees. I would fuck her from behind and as I did I always admired her ass. It was perfect, round, firm, plump and not a blemish on it. Neither of us had ever tried anal sex but we both got turned on with me fondling her bottom and touching her anus. 

I always made sure she orgamsed first before I had her get on all fours. Her ass was haunting me and I wanted to do more. I read up on anal sex and anal foreplay. Soon, I was kissing her buttocks and tickling her anus with my tongue. Jane thought that was somewhat dirty, so I asked her to douche her ass before we were to have sex. I knew that she always douched her pussy.

So, the next time we had sex, she told me she was clean and I sensed some excitement in her voice. After I fucked her and she orgamsed, it was time for anal foreplay. She loved it when I licked her anus and when I went back and forth between her pussy and nether hole, she went wild. I put a moistened finger in her bottom but it was still tight and I didn't want to cause any pain.

I did some more research and learned about lube, anal beads and butt plugs. Those were the things I would use to train her ass and get it ready for my cock. I was on a mission now and I just had to have that ass. The next time we were into anal foreplay, I broke out the lube and greased her bottom. She liked my finger in her bum as I rubbed her clit. From there we progressed to the anal beads and she adjusted to those in time.

One night I had all five beds in her ass and I was eating her pussy. When she began to climax, I pulled the beads out slowly. Her body jerked as each one cleared her anus and she drenched my face. She held my head to her womb so tightly, I thought she would smother me. It was her most intense orgasms ever and she was hooked on the beads. 

Next after another session with the beads, I pushed the anal plug into her and fucked her. Again, she went wild with the sensation of her ass being full. Finally, it was time for anal penetration and I was so anxious that I hoped that I didn't cum too soon. After she had had multiple orgasms and seemed totally relaxed, I put her on all fours again and this time eased my well-lubed cock into her well-lubed ass. The fit was snug and she felt the pressure.

We were both determined to make it work and not cause any pain. It seemed to take hours before I was able to put half of my cock in her ass. I rocked back and forth but I was so turned on that I came quickly and flooded her rectum. As it turned out she loved the feeling of cum shooting into her bottom. That was our first time but it wasn't our last. I still remember her on all fours in that school uniform with my cock in her bottom. It was the most erotic sight ever.

"So, did you become regular anal lovers after that first time?"

"Oh yeah and over time she was able to take my entire cock in her ass and she always wanted me to cum in her."

"Where did you get the beads and butt plug?"

"There was an adult novelty and book store in town." 

"Wow, were you always dressed when you had sex?"

"Most of the time because of logistics. A few times we went to a motel and we liked being naked together. Jane was a cheerleader and I played on the team. A few times I fucked her in her cheerleader uniform."

"That sounds wild."

"It was once. We did it on the team bus after everyone had left. We were seated together in the back and I was playing with her pussy on the ride back to school. She was rubbing my cock through my pants. We got off the bus and then back on after the coach had done his check up and down the aisle. Jane spread out on the back seat and I pulled her panty to the side and slipped my cock in her pussy. She orgamsed quickly so I moved her to all fours. Using sport cream from my bag, lubed her bottom and my cock. Then I slipped my dick in her ass and fucked her until I came in her. It was totally erotic to see her with her cheerleading skirt flipped up over her back with me butt fucking her."

"That does sound hot. Is it erotic when I am bent over your desk with my skirt flipped up and my panties down around my knees?"

"More than you know. I love that look."

"How long did you and Jane have anal sex?"

"Just through college, about two years."

"That's good to know. You have been fucking my ass for nearly three years now. Getting tired of it yet?"

"Never, now I want to hear your story."

ANNIE'S STORY

When I first graduated from college, I took a job with one of two big firms in the town. I soon learned that most of the women were into power fucking. They like fucking guys with important jobs. It was ridiculous. If a guy had a high position in the company, he had his choice of women. There were more divorces than you could imagine. If an executive had a hot babe, there were five others trying to take her place.

I didn't get caught up in that bullshit and a few girls and I would go clubbing and avoid the company waterholes. One night my good friend Deidre and I were clubbing and the three good looking guys came on to us. We danced and drank with them and then suddenly, I realized that Deidre and one of the guys had left. I was left with the other two named Vern and Nick. We danced and drank some more and I clearly had too much to drink.

The next thing I knew was that I was in their apartment and we were all naked in one bed. I was horny and the guys were hot so I was up for them fucking me. After they took care of my pussy, I was placed on all fours and Nick shoved his cock in my mouth. Vern knelt behind me and put his dick back in my pussy. He was playing with my ass and I realized that he was lubricating it and fingering it. Suddenly he moved his cock from my pussy to my ass and eased it in my bottom. Nick held my head in place and fucked my face.

Probably, if I wasn't drunk, I might have protested the anal sex. However, Vern had a slender cock and it didn't feel too bad. The longer he fucked my ass the more I became accustomed to it. When he came in my ass, I actually like the sensation of the warm seed shooting into me. I thought that Nick was going to cum in my mouth but he wanted my ass too. He was longer and thicker than Vern and I was a bit worried. Again, if I was sober, I probably would have resisted.

He was gentle in spite of his urgency to fuck my ass. I could feel him working his cock and feeding it to me gradually. He kept squirting some kind of lube on it and soon I was able to take it. I had never felt so full there in my life, even when I was constipated. Vern put his cock back in my mouth and fondled my tits while Nick fucked me. When he came in my ass, it felt soothing and erotic.

Then Vern was back in my ass and he fucked me until he came again. I had a steady stream of semen oozing out of my anus and running down over my pussy and inner thighs. Nick was back in my ass a second time and it went in a lot easier. He came in me adding to the three loads in my rectum. They were so enamored with my they both fucked me a third time. I felt bloated and constipated.

I crashed at their place and in the morning, they both fucked my pussy until I couldn't cum any more. Then they were at my ass again and filled my rectum with two loads. I was allowed to shower and cleanup. They encouraged me to douche my ass and later I learned why. These guys were big into anal and they loved rimming a hot ass. After breakfast they worked me into a frenzy as they took turns licking and probing my anus.

They also worked themselves into a state of desire and they both fucked my ass again. I was hot so they ate my pussy and sucked my tits until I orgasmed. I thought that I would leave after lunch but no, they showered with me and douched my ass again. After lunch, there was more anal foreplay and lots of rimming. After dinner they fucked my ass for a third time. 

I ended up staying at their place Saturday night and on Sunday it was a repeat performance. Finally, after lunch, I was able to dress and they took me home. It took days for the sensation in my bottom to subside. However, I was glad that I had the experience because I ended up liking it. After that anal sex was something I enjoyed but I was very select with whom I let in my ass.

"Jesus Annie, that is some fucking story. I got a boner listening to you."

"Well save it for later, let's order some lunch."

"Right, one question, was Nick as big as me?"

"God no, I would have never survived you that night. Not for the first time. You're still the biggest to ever go there."

LUNCH AND THE OFFICE

They had a leisurely lunch and another glass of wine. As anxious as they were to get back to the office for sexual fulfillment, they did not rush it. It was about 3:00 PM when they arrived at the office and everyone was gone. They had the outside office and Wally's office to themselves. They locked the main door and then the door to Wally's office as well. They were assured complete privacy. Wally took the lubricant and paper towels from his desk door as Annie leaned over and awaited the next move. He lifted her dress up and draped it over her back baring her panty covered derriere. Annie was wearing thigh high hose with elastic tops and she looked incredibly sexy.

He pulled her panties down to her knees and fondled her shapely bottom for several minutes. His cock was throbbing, so he dropped his pants which fell to his ankles and pushed his underwear to his knees. Taking the lube, he applied it liberally to her anus and his cock. Stepping in closer, he eased his cock into her ass and fed it to her ever so slowly. He loved to watch the slow penetration as his cock disappeared between her curvy buttocks.

Holding onto the magnificent hillocks, he began to fuck her ass and savored every moment. As many times as they had had anal sex over the past three years, he never tired of moments like these. It was the most erotic sight for him to witness his cock in her scrumptious derriere. He was good for two ejaculations and often three depending on the time span. So, it didn't concern him when he felt the first one approach.

Feeling that he would shoot at any second, he pulled his cock from her rectum and aimed it at her cheeks and anus. Several forceful streams covered her bottom and gobs of semen gathered around the rubbery ring. Wally pushed his cock back in and fucked her with a few strokes. He then pulled back out, gathered up some of his seed and re-entered her ass. He did this several times and then backed away. Using the paper towels, he cleaned off her buttocks and wiped his cock. Annie turned around and smiled.

"That got me really hot, here eat my pussy."

She stretched back on the desk and spread her legs lifting her knees to her chest. Wasting no time, Wally knelt down and buried his face in her quim. Annie loved to be eaten and he was the best she ever had. She too was turned on quickly and announced that she was going to cum. He stayed glued to her vagina and felt the surge of her climax. He continued to lick her and tease her clit until she pushed him away.

"There is no one else here, let's get naked," she whispered.

They both stripped and Annie got on the carpeted floor on all fours. Wally went back to his desk and retrieved two vibrating dildos. He turned one of them on and lubed it thoroughly. He eased into her ass and she gasped at the sensation. He moved it in and out as if it were another cock fucking her ass. Then he got the second one, turned it on and put in her pussy. Keeling off to the side he used both dildos to fuck her ass and pussy simultaneously.

Annie was going wild with the vibrating action and she rotated her ass signaling her pleasure. Wally then began an alternating pattern with the dildos. He pushed one in her ass and pulled back on the one in her pussy. Then he pulled the one in her ass back and plunged the other one into her womb. He got a good pace going and neither dildo ever left her body.

His cock was stiff and he was ready for more action. He removed the dildo from her anus and stood over her straddling her fantastic ass. Leaving the dildo in her pussy, he eased his cock back into her bottom, squatted over her and fucked her ass a second time. He could feel the vibrations from the dildo through the thin membrane. They were both incredibly turned on. Annie loved the sensations and she experienced and intense orgasm when she climaxed. 

Wally was not far behind her and this time he left his cock in her rectum. He shot a large load into her chamber filling it with the warm syrupy discharge. She used her sphincter to squeeze his shaft. He loved it when she milked his cock like that. He stayed in her until he felt his pecker soften and then he eased it out. Some of his seed bubbled up in her anus and he blotted it with a paper towel. 

Checking the time, he saw it was nearly 5:00 PM. It had been another glorious anal encounter between them lasting nearly two hours. They would clean up in the restrooms, dress and then head to their homes for the weekend. Wally was straightening up his desk and putting the sex items away when Annie returned.

"Any big plans this weekend?"

"No, Donni is flying in late tonight, her flight gets in around midnight. We will probably go to the fireworks over the weekend. One of the neighbors invited us over for a cookout. What about you and Jerry?"

"Kind of the same thing. We'll go to his parents for a cookout and watch the fireworks from their yard."

"Well, have a good weekend. I'll see you Tuesday."

"Yeah thanks, you too."

Annie left the office before Wally. He finished straightening up and then locked up before he left. His live-in girlfriend Donni, a flight attendant, was usually gone two or three nights a week which made it easy for Wally to hook up with Annie. Her steady, Jerry, traveled often and provided her with the opportunity to be with Wally. When both were out of town at the same time, Wally and Annie spent the evening at a romantic interlude. They loved the room with a Jacuzzi and spent hours of anal love making. 

TEN DAYS LATER

Annie and Wally had the evening to each other as their significant others were out of town. The romantic interlude was booked solid but Wally was able to find a hotel room with a Jacuzzi tub. It was a bit of a drive from the office so Annie drove to her place and Wally picked her up. An hour later they were in the hotel room naked with the Jacuzzi tub filling with water. Annie loved to soak in the bath oil and she added plenty of beads as the tub filled. They showered first and she douched her bottom as she looked forward to the anal foreplay.

There weren't many things that Annie liked more than being rimmed. She loved to be in the oily bath water, leaning over the side of the tub with Wally's tongue in her anus. He had a way of licking her and probing her that drove her mad with desire. His tongue worked its magic from her pussy to her anus and back again. She always orgasmed with the dual stimulation and then she was ready for anything.

With the water being so oily, it was easy for her to take his cock in her bum. Wally pulled her back onto his lap and guided his cock into her ass. Annie gasped as the entire length filled her slowly. Using his strength, he lifted her up and down on his rigid shaft. She aided him by placing her feet on the surface and lifting her hips. They had a smooth rhythm going and he knew he was close.

Feeling the buildup, he held her tightly in his lap and released his load into her rectum. It was a massive ejaculation and it flooded her chamber. Annie remained seated in his lap until his cock stopped pulsating. With his help, she eased her body off of him and felt the semen rush out into the bath water. She moved to the side and found a forceful jet to help douche her anus. Annie had done that many times before and she loved the soothing feel of the jet caressing her bottom.

They cuddled for a while in the bath. He wrapped his arms around her and fondled her smallish tits. They always felt good in the oily water. The water started to cool down so it was time to get out. They dried off and moved to the bed. Annie lay face down on the bed and awaited her massage which always followed the Jacuzzi session. Wally would briefly massage her shoulders, back and legs but move very quickly to her super fine ass.

He would spend nearly thirty minutes massaging her lovely buttocks and fingering her anus. They both savored the attention to her fantastic ass. It seemed that he could play with her cheeks all night. However, they both got turned on and Wally was ready to dip his dick back in that sweet bottom. She was well lubed so he lifted her by her hips and moved in behind. Her face was on the bed turned to one side and she had that dreamy look of total submission. Wally eased his cock into her shapely bottom yet again and as he looked at her, he knew that he would never get tired of fucking her ass.

"Annie, I can't begin to describe how sensuous you look with my cock in your beautiful ass."

"I love your cock in there. It feels so wicked, naughty but erotic at the same time."

Wally caressed her buns as he always did when he fucked her slowly. The sight of his cock sliding in and out between the buttocks was fantastic. Annie had the perfect bottom for anal sex and he loved being in it. If it were possible, he would have stayed in it all night. However, the sensuality of the moment caught up with him and he felt that all too familiar twinge in his loins. He pressed forward against her globes and released another load in her rectum. 

As she always did, she used her talented sphincter to grip and release the thick shaft. That act in itself was a marvelous feeling. The ejaculation wasn't as voluminous as his first but still substantial. As he eased his dick out of her bottom, semen oozed out of her anus and trickled down over her vagina and dripping on the bed sheets. Annie used her sphincter to force most of it out and it was another erotic gesture. 

Annie was turned on and her pussy needed attention. She rolled over, parted her legs and patted her pussy inviting him to eat her. Wally wasted no time and got between her legs. Using the bed sheet, he wiped his seed from her vagina and then went to work on her. She loved to be eaten and he loved pleasing her. As she got close to her climax, she wrapped her legs around his neck and lifted her hips off the bed. Normally when in the office she covered her mouth with her arm to muffle her cries of ecstasy but in the hotel room she let it all out.

Her body went rigid, her legs tightened around his neck and she drenched his face with her love juice. As she climaxed, she groaned and bellowed loudly. Wally laughed to himself as he had forgotten how expressive she could be when she orgasmed. He wondered if the guests on either side of their room could hear her. He was certain they did if they were in their room. After her outcry, her body went limp, her legs released his neck and she collapsed on the bed.

"Oh, was that ever something, that was so good. I love to cum like that."

"You definitely got off, that's for sure!"

"Do me a favor and run the Jacuzzi tub again."

"Sure, the water is cold so I'll refill it."

"Add plenty of bath oil. I want to feel slick all over and I want your cock in my ass again." 

Wally smiled as he eased his muscular frame off the bed. He drained the tub and refilled it with hot water, adding the bath oil beads. Annie was in a euphoric state and she lay in bed caressing her body. She loved arousing her nipples and fondling her breasts. When the tub was ready, he picked her up and carried her to it. He deposited her in the water and then joined her. 

She sat in front of him again and he fondled her cute titties. Without saying anything she moved to the side to the tub and leaned over it presenting her ass to him. It looked delicious covered with oily water. He planted kisses on her buttocks and then pried them apart to get to her nether hole. He ran his tongue up and down in the crevice and let it dart into her anus. His cock was throbbing and he was ready to take her ass for a third time.

He got behind her and slipped his oily dick into her rectum. Once all the way in, he began the slow fucking rhythm that they both loved. The best thing about cumming a third time was that it took much longer and he loved the time spent in her ass. It seemed like they fucked for hours before he finally ejaculated a third time. Annie loved it as much as he did. They stayed coupled together for several minutes before they separated and relaxed in the bubbly water.

It had been a fantastic evening and they were both sexually sated. They showered dressed and he drove Annie home. They could have stayed in the hotel overnight but they didn't want to wear the same clothes to work the next day. On his drive back to his place, he reflected on the three-year affair. They had never gotten bored with each other and always managed to keep their sex exciting. He didn't know how much longer it would last but at the moment, there was no end in sight. He was already looking forward to their next anal encounter.