Coupling Coworkers Ch. 16

Since Sara had started her sexual fasting in preparation for her weekend working for Keith, I was looking forward to Kevin and Christy's pool party/orgy on Thursday. Missy and I went together since neither of our spouses were attending, Sara because of her fast and Mark was in New York.

All of our usual coworkers with their spouses, Donna and Rachael, were there and a few of Christy and Kevin's friends and, just as I expected, it took only about thirty minutes before it was an all-out orgy fest. Fourteen bodies were intertwined either in the pool or on the patio in some type of sexual combination.

I had a wonderful session with Christy. After she had brought me to an orgasm, she introduced me to her friend Tonya. However, Tonya was busy with Donna's husband Tom fucking her from behind, which meant I had to settle for a blowjob until her was finished. After he finished, she then took over and rode me as I sat on a lounge chair until I had cum again.

After cumming with Tonya, I needed a break and headed into the kitchen to get a drink of water, which was about the only drink not available on the patio. As I filled a glass of water, I saw Rachael come into the kitchen behind me.

"Great party," I said watching Rachael come to me as naked as a jaybird. It was amazing how wrong I had been about her. I had always pegged her to be a shy, conservative girl, but her work at the football game proved otherwise. However, she had not seemed interested in doing more since then. At least not until that night.

"Yeah," she replied as awkwardly as I had when I started the conversation seconds ago. "I guess you can't go wrong with a party where everyone has sex."

"Good point," I said sensing she seemed nervous talking to me, but I could not figure out why. "Except, this seems more like fucking than sex to me. It might be a semantics issue, but I think it's the fucking like mad animals that makes this so fun."

"That's the same thing Aaron said," she said referring to her boyfriend. "In fact, he says that's why we love to have sex with others. No pressure, just fucking."

"And you agree or not," I said when she paused.

"Oh, I agree, it's just....."

"Just what? Don't be shy. We're standing here naked in Christy's kitchen after I have just fucked her and I saw you fucking Kevin."

"Well...It's just that I have a dilemma."

"Can I help?"

"That's what I was hoping for."

"If I can help, then I'll be more than happy to help you out. What do you need."

"Well, it's just that Kevin has been asking me to do something," she started in a very nervous voice.

"And you don't know if you want to do it?"

"No, that's not it. It's just that I've told him I've already done it before, but I haven't."

"What's 'it'?"

"Anal."

"He wants you to do anal, but you've never done it before, but you've said you have and you don't to look like an idiot to him if it doesn't turn out like you expect it to, right?"

"Yeah, that's pretty much it. The other day we were having a foursome with some friends of ours and he mentioned having the guy fuck me in the ass. I was able to talk my way out of doing at that moment, but I don't know if I'll be able to in the future. Anyway, Missy and Donna told me that you and Sara do anal all the time and that you'd be able to ease me into it so that I can do it with Aaron more comfortably than if it was my first time."

I paused to slow down the conversation. She had delivered the last lines as if she had rehearsed them in her head a million times and just wanted to get it of her mouth as fast as possible.

"I think I can help," I said matter-of-factly. I would be a fool to turn down this request. How often do pretty girls come up to you and ask you to help them do anal for the first time.

"That's wonderful," she said giving me a hug and pressing her naked body against me. "I was so nervous. I don't know why, but...I don't know why. I guess I thought you'd think I was a prude because I've done anal before."

"No, not at all. Sara's working at her new job this weekend...you know her sex job, so why don't you come over Saturday. Is that good?"

"You bet," Rachael said giving my growing cock a little tug. "You'll be a great teacher. Besides, the size of your cock will teach me and make most others easier to handle."

"Well, since we've got Saturday together, let's go back out to the party and find some others to have sex with...I mean fuck."

We headed back outside. I did not see Rachael much more that night, but after several more orgasms I was completely spent. It was around 2:00 in the morning before Missy and I left.

Friday flew by. Mark came into town to spend some time with his wife so they went to a cabin they have in a rural area around here. After Sara left for Keith's I was home alone. I found it relaxing to have the place to myself. However, I was not able to abstain altogether from sex. After some internet searching, I found myself hard and had to relieve myself.

Once Saturday arrived, I could not wait for Rachael to get here. Sara's phone call mid-morning only served to get me even more excited. She told me everything that had happened to her on Friday and what could possible happen Saturday night.

The only way that Saturday would go by fast was to lie down for a nap, which ate up most of my afternoon. Finally, at 7:30, I heard a knock at the door. It was Rachael.

As I let her in the door, I took the usual look at how she looked. She looked great in a pink halter and white jogging pants. She did not seem nervous, but I could tell she was entirely comfortable either.

I offered her a drink and she readily accepted. After taking two full pulls on a bottle of scotch, she just simply looked at me and said she was ready.

I led her to the bedroom, where I had set everything up, mostly just making sure there were condoms and lube ready to go.

"So, what's first," she asked as she sat on the edge of the bed.

"Well, I can't say that I'm an expert at teaching this, but Sara and Missy have told me that anal is usually best when it's done as just part of having sex, especially after already having an orgasm or two."

"Since I have no clue, I'll just follow your lead."

I sat on the bed next to her and moved in to kiss her. Her lips met mine and we soon had our tongues dancing together. I slowly moved her onto her back and began to kiss her ear and neck, while my other hand slowly worked up her shirt. I found out she was not wearing a bra when my hand reached her tiny breasts.

As my hand ran over her nipples, which were rock hard, she pulled into me and moan escaped her mouth. I slowly worked her top over her tits and then began to kiss her nipples while my hand moved lower and lower. Before long, my hand found a resting place between her legs and I began to massage her pubic region through her jogging pants and panties.

Slowly, I worked my way down her abdomen to where her pants began. I moved off the bed and knelt in front of her as I slid her pants and panties off. Spreading her legs wide, I moved back in and began to lap away at her tender pussy.

It did not take long before her hips were rotating and moans were escaping her mouth. She used one of her hands to massage her clit as I licked her pussy and her other hand alternated between brushing through my hair and pulling my head into her pelvis.

As I sensed she might be close to orgasm, I pulled away. I stood up and removed my clothes before I lay down on the bed next to her. I pulled a condom off the dresser and had her put it on. Immediately after that, I pulled over me and had her sit back down, impaling herself on my cock.

Starting slowly at first, but soon picking up the pace, Rachael moved me in and out of her as she rotated her hips back and forth. I had brought her close enough to orgasm before, that it took only a few minutes before a huge orgasm ripped through her body. She collapsed onto me after the pleasure had subsided.

"Are you ready," I asked after she had taken a moment to catch her breath.

"Yeah," she purred into me ear. "You want me on my hands and knees?"

"No. It's easier to start with you on your back, so slide over to the edge of the bed."

She obeyed. I saw on her face as I got the lube of the bedside table that she did not seem apprehensive anymore. Of course, a good solid orgasm usually will do that for people.

"Tell me if it hurts to much and I'll adjust, okay," I said as I applied lube to my condom covered cock.

"Okay," she nodded.

I used the extra lube on my hand to lube the opening of her ass. As I did this, an audible moan of pleasure escaped her mouth.

"Let's start first with just a finger," I said as I slowly entered my lubed index finger into her ass. "How does that feel?"

"Fucking awesome," Rachael replied.

"Ahhhhh, that's not so good," she said to me as I slid in a second finger. Her eyes were now open.

"Let me keep my second finger in, your muscles will relax quicker if we just stay with it, okay."

She nodded and it took only another few moments before the look of discomfort faded from her face. It was now time to move on.

I withdrew my fingers and replaced them with my cock at the opening of her ass. Slowly, I pushed the tip of my cock against her asshole. I looked to see her expression and although her eyes were closed, there seemed to be no indication of discomfort. Using this as a gauge, I pushed a little further in, now my helmet entirely in her ass.

"Ahhhhh...FUCK THAT HURTS," Rachael screamed.

"You want me to pull out or keep going," I asked stopping my move into her ass.

"Keep going, but slowly," she said, biting her bottom lip.

I pushed in another few inches, her face gripped with pain, but with a sense of pleasure in it also.

"I'll stay here for a little bit, until you get used to it. Believe it or not, but it won't be long until her sphincter relaxes."

I stayed completely still while she adjusted to her asshole being penetrated. After a minute or two, she told me to continue. Again, I moved only about another inch into her, but this time she did not scream out in pain.

"Does this hurt still," I asked.

"Yeah, but it hurts in a good way. I don't know if it's more painful or more pleasurable, or both."

"Sara has told me the same thing," I said pushing another into her ass another inch or so.

I now had half of my cock in her ass, but I was not making any other movements other than the small, incremental movements into her ass. We continued this way for another five minutes or so, until I had three-quarters of my cock in her.

"How do you feel," I asked, knowing that I was not going to go further into her in this position.

"Good," she replied. "I really thought this was going to be a lot more painful. It hurts, but it's okay."

"Outstanding," I said happy with my instruction skills. "Now, it's time to fuck, but you need to control it at first. Sara claims that girl on top, reverse style, is the best way. I have no idea, but I guess we should try that first."

"Whatever you say, master teacher of my ass," Rachael said with a big sarcastic smile on her face.

We rearranged on the bed. Rachael lowered her ass onto my cock. At first, she took only half of me into her before she started moving along the length of the cock that was in her ass. However, three-quarters of my cock soon replaced that half, which was then replaced by the fact she was now bouncing her ass up and down on the entire length of my cock.

I did not need to ask if she was okay, because she was soon moving quickly and experiencing her first-ever anal orgasm.

"Fuck my ass like they do in porn movies," Rachael said to me after she had recovered from her orgasm. "As hard as you can. I can't fucking believe that I've never done this before. It's so fucking awesome. The pain and pleasure together...fuck it's awesome."

As she talked, she had moved onto her hands and knees and I had moved behind her. I stood on the bed and crouched down lowering myself and my cock to her ass, which was now gaping open. Without the tenderness of before, I plunged my cock entirely into her wide asshole.

Rachael led out a small yelp as I began to fuck her asshole. After a minute, I picked up the pace even more and I slammed into her, my pelvic bone hitting her tail bone.

"FFUUUUUCKKCKKKKK....YYYYYYEYEEEYAAAAAAHHHHHHHH....FUUUFFUUUUUUUCKKKKKKKK MMMMYYYYYY ASSSSSSSSS," she screamed in pain and pleasure at the same time, experiencing a couple of back-to-back orgasms.

Because of the tightness, I did not take long before I was ready to cum myself. Since I had a condom on, I came as I continued to fuck her ass. The spasms of my orgasming cock brought her to another orgasm as I slowed.

After my orgasm subsided, I collapsed next to her, and she next to me. We laid next to each other in silence for a few minutes, each catching our respective breath.

"So how was her first time in the ass," I asked, breaking the silence.

"Not bad. I think my asshole might burn right off my body right now, but I thought anal was much more painful. I never imagined ever having an orgasm doing it, let alone three or four."

"I'm glad I could be of some help."

"You were, but I've got to go now. I'm meeting some friends"

With that she was off the bed and putting her clothes back on. After she had dressed, she climbed back onto the bed and crawled over to where I was still lying. "Thank you," she said giving me a deep kiss.

"Any time. I don't think I've ever turned down an opportunity to have sex, let alone anal sex."

"That's good to know," Rachael said getting back off the bed. "I'll let myself out, but I might need your services again. Aaron might want to have me do a double penetration."

"Aaron might want it, or you want it," I asked.

"Okay, I might talk Aaron into a dp. I'll let you know."

She blew me another kiss and walked out of the bedroom. Feeling completely satisfied from not only a sexual standpoint, but from an ego standpoint as well, I drifted off to sleep. Not a bad night for me, even with my wife busy getting her brain fucked out at some party.

At least this time I will have something to report to her about the weekend when she fills me in on the details of her weekend.