Working Holiday Part Twenty-Six: Afternoon Affairs

Read part one here.

When I left Rhiannon at the motorcycle club, I knew she'd be well taken care of, literally and figuratively. Through my friend there, I had met a girl who had experienced the bitch treatment. It was not for every girl, certainly, but I was sure it was something Rhiannon would appreciate.

I was waiting for a call to pick her up so I was not surprised when the phone rang. With some excitement, she told me they asked her to dance at a strip club that evening. Oh, and that she had a great time serving the club members—that was almost an afterthought on her part!

I had planned a reasonably quiet night for her, but so long as she was game for some new adventure, I heartily approved. Stripping was one idea I had not planned for her because I didn't have any reliable contacts at any of the clubs.

I'd planned for her to make a profile on an adult “dating” site and see what transpired. She had done her share of whoring for the week so I figured a bit of flirting would do her good. I thought she might enjoy hooking up with a few married men wanting a no-strings-attached affair. We could have received one in the evening and one or two the next day if we planned it right.

When she called again later to say she would do a private show for a bachelor party, that put the brakes on the flirting idea, but her new adventure was certainly better than my plan. Especially when she admitted that it was a full service affair. I could hear the excitement in her voice as she told me about her experience at the club and what might await her at the party.

I estimated that she wouldn't be back until close to midnight. I had already created a profile for her, including some photos that obscured her face but left little else to the imagination. The images from our garage shoot that week went to good use. Rhiannon had received a number of interesting inquiries within fifteen minutes of posting her ad. The site was very active that evening.

Initially, I left the messages to her unanswered, wanting to involve her in the decision process. I did take the time to examine each man's profile. They were a mixed lot of guys looking for cheap thrills, some were rather pathetic, unfortunately. I made note of the more worthy candidates for her consideration later.

When the phone rang. she had quite the story to tell. She fucked most of the guys at the party, including her former professor. She was thrilled by the experience, but even more thrilled that the man asked her to stay with him that night. Although it threw a wrench into my plans, I had to admit that she would have a much better time with her old teacher—I knew how much she fantasied about such things. I wished her luck and told her to call me in the morning and let me know she was all right.

I went back to the dating site and checked her new messages. If she was going to bed an older guy that night, I thought it opportune to lay some young studs on her next. I reviewed the profiles of her potential suitors and responded to the college boys, judging which might be game for a quickie with Rhiannon the next day. After a couple hours of messaging, I narrowed the field down to six guys.

It was likely that Rhiannon would not make it back until after lunch on Friday, so I gave each guy a specific time to arrive in the afternoon and a specific time to leave. I made it clear that she was cheating on her boyfriend and that she could only give the guy half an hour of her time. As her, I told them that there was no risk her boyfriend coming home, but she only wanted a quick fuck so she could get through the weekend. Every one of them agreed to “her” conditions.

It was strange to go to bed alone that night. I had grown accustomed to fucking Rhiannon before we slept … and then fucking her again in the morning. I liked drifting off to sleep with my hand between her legs or with her cupping my balls. I was also thankful to have the bed to myself again so I could relax. She was a demanding lover; then again, I was equally demanding. I fell asleep while imaging what she was doing with her old professor.

I love sex first thing in the morning. I usually wake up with an erection; waking up with a soft girl beside me gives me someplace to put it. Her hair is messy, she has no make up, but she has a rested look that is a different type of beauty. Every girl hates to kiss before brushing our teeth, so I don't kiss, unless I lick her pussy to warm her up. After that, it's a quick fuck and leisurely cuddle before hitting the shower and sometimes fucking again. No matter how bad the rest of the day might be, you can always think back to how it started and smile.

I lay in my bed for some time and had to resist the temptation to masturbate. I had cum so many times that week but thinking about what she might gotten herself into the night before was painfully stimulating. Holding off would also enable me to enjoy her more when I did see her again.

There were no messages on my phone. I wondered if I should text her, but there was really no point. She was either in trouble and couldn't get my message anyway, or she was in good hands, in which case my message was pointless.

After cleaning up, I checked her messages on the dating site. She had plenty of requests from potential suitors. One of the guys she was scheduled to see that afternoon regretfully canceled and asked if he could see her another day. I checked through the profiles of the new guys and sent a message to the most promising of the bunch. Two hours later I had replaced the canceled date.

Rhiannon messaged me just before lunch that she was on her way back and that she had a most agreeable time with her professor. I had her suck me off as soon as she came through the door. She told me it was the second time that day she gave a guy a blow-job in a doorway. I threw her on the bed and rammed my dick in her and demanded she tell me about her night.

I took it slow so she could fill me in on the details. She began by apologizing that she had a load of cum in her already. She had to keep her legs crossed on the metro so as not to leak too much. I could feel nothing, of course, but I'm glad I hadn't gone down on her!

I didn't mind fucking Rhiannon while another guy's splooge was sloshing around in her cunt. I'd shared a girl with a couple of guys before and I learned to get over it. On the first occasion, I was at a party and was introduced to a girl with a reputation as a slut. She was decent enough looking and damn friendly. Everyone was drinking and having a good time. I ended up making out with her and was all set to drag her off into the bushes (it was a party at a country cottage), but she dashed off to meet some new guests and I was left with blue balls. There were other girls at the party, some of them were particularly hot and most were attired in beach clothing, revealing a lot of flesh and adding to my horniness. When I next saw my slut, the combination of liquor and hormones had me riled up enough to confront her. I was still in my teens then, you see, and was rather foolish (not that I've improved on that much). “Look,” I said, “I'm horny as a two peckered bull and you're the only one who can help me.” Maybe she was impressed with my bravado or maybe she was as horny and drunk as me, but that line would never work again. I followed her to a bedroom and we made out on the bed. In my eagerness, I practically tore her clothes off. When she told me not to go down on her, I asked why. I hadn't planned to eat her out, but I was curious. She told me she just had sex with another guy. Well, as I say, I was horny as hell and taking “sloppy seconds” was not going to stop me, particularly after being liquored up so. Ten minutes later, my load was deposited inside her and we lay together for a few minutes. I think I dozed off because the next thing I remember, she was getting dressed.

The second time I became an Eskimo brother was when a pal called me with a strange proposition. A friend of his was looking for a few guys to gangbang his girl. The requirements were that they had to be total strangers, be tested clean, and to reasonably fit and well groomed. I had recently moved to Montreal and only just discovered the libertine attitude of many of the inhabitants. I showed up at the hotel room the couple had rented for their play, girded for whatever might happen next. The boyfriend met me at the door to make sure I was acceptable. My pal was not there. The girl was OK looking, but had a dynamite body; firm stomach, soft round breasts and a tightly muscled ass. There were five guys, including her boyfriend. She started by sucking our dicks, one after another. Her boyfriend mounted her, as if to show us how it was done, and then the action began in earnest. She was really vocal. Until that time, I'd never heard a girl demand to be fucked as much as she did. She really spurred us on. When she screamed that she wanted all our cum inside her, I thought it was just for effect, but she really insisted that she wanted a super cream pie. At the end of about an hour of fucking, we each planted our load deep inside her. I was third in line so I my dick was smeared in the semen of two other men when I pulled out. As the next guy in line boarded her, I had her suck my cock good and clean. We men just stood around and waited until she was topped up. She lay on her back and played with her pussy, letting the cum cocktail ooze out, giving us quite a show.

I suppose it might have bothered me to take sloppy seconds with a girl to whom I was emotionally attached, but I didn't feel possessive with Rhiannon (not that I'm possessive to begin with). In a terribly perverted way, I felt fatherly toward her. Of course it didn't help when she would occasionally call call me “Daddy” during our sex play. In fact, that rather turned me on. We talked about the idea of roll playing a father and daughter scenario, but we never got around to it.

I thought of Rhiannon as a flower that attracted many bees. The more she was pollinated, the more happy and lovely she was. That was the point of my setting her up so many times that week. In all the years I'd known her, I never saw her glow as much as she did.

I told her about my plan for her that afternoon and she liked the idea. She was sorry she couldn't help me pick the men, but she was also glad that I took on the responsibility so she could be surprised. Rhiannon liked surprises.

We showered and she carefully flushed out her professor's seed. She also gave herself an enema in case she decided to give the boys some back door action later. I had her wear her schoolgirl skirt and white blouse to meet her dates. She didn't wear underwear, of course. While she made the bed, I straightened up the apartment, putting away the small valuables and anything that might identify either of us.

While we waited, I showed her the men I selected and the messages that I sent on her behalf. She was disappointed they were all young guys, but I said I was trying to give her some variety. I also knew that she would appreciate the experienced men all the more after a few hours with the young bucks.

The first guy arrived exactly on time; he was an eager fellow. I went into my office and tried to get some work done while she ushered him into the bedroom and went right to business. I couldn't really hear anything from where I was, but I could occasionally hear her cry out in passion. Half an hour later, I heard her walk him to the door.

I stepped out of my office and she pranced over. “You wanna fuck me?” she said. A girl doesn't have to ask me that question twice. I have to admit that I had a huge boner the past thirty minutes and it needed seeing to. I'm not much for voyeurism, but knowing she was nailing some guy in the next room really got my blood pumping.

She was still plenty wet from the stranger, so I entered her right away. I gave her a good fuck before asking her about the details of her experience. The guy was only somewhat experienced, being a couple years younger than her. She brought him into the bedroom and he was so excited that she decided to just lay back on the bed with her legs spread and let him take her. He pulled off his pants, applied a condom and mounted her without any foreplay.

He came too quickly, unfortunately. He made it up to her by giving her pussy a good licking. Rhiannon returned the favor by sucking his cock hard and blew him until he came in her mouth. I told her I thought she had semen breath and she tried to kiss me. I pushed her back and laughed, then fucked her some more.

We didn't have much time before the next guy would arrive. I donned my robe and she straightened the bed and got dressed. The next guy arrived right on time.

I sat in my office and got no work done at all. I ended up browsing porn, careful to keep the volume off. When the door closed, I opened my office to see her smiling and looking at the fabric tenting out from my crotch. She asked me if I wanted to fuck her again and I gave her the same reply … and the same treatment.

The second guy was a nervous wreck. He couldn't even get hard until she sucked him for almost ten minutes. He was in such danger of cuming that he put on a condom and got straight to business. The business quickly went bankrupt, however. I thought she was going to tell me he prematurely ejaculated, but it was worse; he lost his erection. This guy was only twenty years old! She ended up blowing him until he shot his load down her throat. “He did have a lot of cum, though!” she told me (I heard her gag and cough as I listened at my office door). I accused her of being a cum slut and she grinned at the compliment. She's such a cum slut that way.

The ringing of the doorbell alerted us to the fact that the next gentleman caller was rather early. Rhiannon threw her clothes on and I beat a hasty retreat to my office, remembering to grab my robe from the bedroom floor. I went back to my computer to see who was visiting and who was still to arrive. I could hear the two of them talking as I listened near the door, but could not make out what they were saying. It was very quiet and she was not moaning. Not a good sign.

It was nearly forty-five minutes before she let him leave. She was naked and laughing when I came out from my room. I gave her a “What the hell happened?” look and she laughed again. She told me she had just initiated a sixteen year old virgin. “No shit, seriously?” I gave her a high-five. The guy's profile said he was a nineteen year old university student. She said he confessed to the deception right away. She made him show his ID to confirm his age. He pulled out his high-school ID card and confessed he had never been with a woman. The kid wasn't bad looking; he probably didn't have a lot of confidence.

She appreciated his candor and agreed to walk with him into the temple of manhood. They got undressed and she lay on her back with her legs open. His eyes were riveted on her shaven pussy. She told him not to bother with the condom, she wanted his first experience to be natural. He maneuvered between her thighs and pushed his penis into the first vagina he had ever touched. Rhiannon was already wet, of course. Once he was inside her, he had no idea what to do next. She had to explain to him how to rock his hips. He followed her instructions and came in only a couple of minutes.

I smiled when she told me how she resisted the urge to pat him on the head and call him a good boy. Instead, she said something along the lines of “You're a man, now,” and kissed him long and hard while his cock throbbed inside her. That was very considerate of her, and quite poetic.

She put him on his back to give him his first ever blow job. To punish him for his deception, she intended to give him such an epic cock sucking that he would think of Rhiannon whenever a girl went down on him.

Ever the naughty girl, she dipped two fingers into her pussy and pulled out some of the young man's spunk. He watched in fascination as she licked her fingers clean. "I love fresh cum," she said. The kid got hard right away, but he blew his second load in only five minutes. The guy was thrilled, of course, she was slightly annoyed because she was only getting warmed up. Rhiannon loved to suck and fuck and this guy let her down. He sensed this and asked what he could do for her. She had him suck her nipples and play with her clit. He had no idea where her clit was, of course, and she was too impatient to teach him. So, she played with herself as he made like a baby on her small breasts.

After she managed to bring herself off, she was surprised to see that he was hard again. Inspired, she got on all fours and had him take her from behind. He did a much better job, plowing her like an old hand instead of a boy. It was then she decided to give him the ultimate hat-trick. It didn't occur to her until I pointed it out, but this was an equally effective punishment for him. Who would ever believe that his first sexual experience included not only vaginal sex, but oral and anal sex, and with an older woman who just happened to be cheating on her boyfriend? She laughed in agreement. 

She didn't trust the guy enough to let him put his fingers in her ass, so she initiated the play by inserting, first one, then two fingers. He said nothing, just happy to be fucking a real girl. Without uncoupling, she took some lube from the night-table and applied it to her asshole. She then had him pull out and lube on his cock. The next part was tricky. She made him hold still and press his cock against her ass. She then backed into him, easing his cock into her ass. When she had him up to his balls, she squeezed and released her sphincter, gripping the base of his cock rhythmically. She could feel him pulsing in response. She told him to go slow and he obliged, sliding in and out of her ass.

At this news, I rolled her over and ass fucked her. I knew she was lubed and ready, so I just slowly pushed open her sphincter with my cock and basked in the forbidden pleasure of her asshole. She admitted that he dropped a load there, too, but I didn't care. She admitted that his first load was huge because the cum was dripping out when she blew him. I noted the large wet spot on the sheets. I wanted to pump my cum into her ass as well, but I also wanted to save myself for that evening. We had a lot more fun still ahead, so I fucked her ass hard and pulled out with an audible “pop.” We changed the sheets and she ran back to the bathroom to clean up and flush out. Her next caller should arrive at any moment.

He was late.

He was more than fifteen minutes late by the time the doorbell rang. I listened as she met him at the bottom of the stairs. He said got off the bus at the wrong stop and got turned around. Rhiannon hurried him to the bedroom and they were at it in moments. This guy knew what he was doing because she was moaning in pleasure. I love to her her moan, whether I'm the cause or not. Just the sounds of her moaning got me hard and I stroked myself as I listened in.

My erection deflated when the doorbell rang. The moaning from the bedroom ceased. I heard Rhiannon's voice. She told her lover that it could not be her boyfriend, but possibly a friend coming for a visit. They quickly dressed and Rhiannon shouted “Just a minute!” through the bedroom window. The problem was to get lover number four out of the apartment while lover number five was on his way in.

She told Four to wait in the bedroom and to straighten the bed. She would lead her “friend” to the kitchen. At that point, the guy could sneak quietly down the stairs. When she opened the door, I could hear her greet her next lover like an old friend. At the top of the stair she said, “Hey, I really need a drink. Do you want to join me?” She told me later that she was not joking; she really did need a drink. The new guy followed her into the kitchen where she picked glasses and choose a bottle from the collection in the pantry.

I knew the fourth guy had left when I heard the front door softly close. I don't doubt the guy was disappointed, but at least he had a few minutes of fun. It would still make a great story for him to regale with his pals back at the college.

Rhiannon took her new man to the bedroom and they were humping like bunnies in no time. She finished with him and sent him on his way. She came for me and I fucked her as she told me how she got rid of lover number four. I was surprised she recovered quickly enough to come up with that strategy. I've seen her half drunk from sex, unable to answer the simplest of questions. We cleaned up once again and waited for her final date to arrive.

Number six did a reasonably good job fucking her, she told me after. She was not in as much a hurry to get rid of him since he was the last. So she let him take his time and cum twice for her. She liked that the young guys came a lot, and that they had a lot of semen for her, but she preferred older guys with more experience. Having a young woman tell you this as you're fucking her with authority is a tremendous aphrodisiac, let me tell you.

“I like having all these men fucking me in a row like that,” she said. She explained how it was different from being fucked as a whore. The men she saw that day were there for her pleasure as well as their own. They were also thrilled to help her cheat on her boyfriend ... in contrast to the men who fucked her that week, who were interested in their own pleasure and mostly cheating on their girlfriends and wives.

She had been “the other woman” on a few occasions and she was always turned on by the idea. Playing the cheater appealed to her because she couldn't picture herself cheating on a serious boyfriend. She enjoyed the role playing.

“What if a boyfriend wanted you to fool around?” I asked. She rightly pointed out that it wouldn't be cheating and she had a good point.

The first time I ever cheated, I justified it to myself very easily. My girlfriend went home for the holidays and I was visiting my mother at her home. My former girlfriend showed up and we both knew that we would be having sex that night; there really was no way around it. While my mother was out with friends, my ex and I retired to my old bedroom and spent two hours reacquainting ourselves. She was a virgin when we met, but had been busy gaining experience. I dismissed our play as “cheating” because Shelly was an old friend and I had no intention of reigniting the flame with her, just comparing notes on our lives in the two years since we last saw each other.

The only other time I cheated was during a long business trip. We had worked hard to complete a project for a very demanding client. There were tense workdays and long evenings to get it all done in time. Upon delivery, the bosses were thrilled and we had a bit of a party at the bar in the hotel where most of us were staying. People from the client's team joined us and there was plenty of drinking and partying. Everyone was excited at the conclusion of the project. I let it get the best of me and ended up in my room with one of the local team members. There had been sexual tension between us from the start, but I was true to my girl and focused on my work. The excitement at the end of the project, our success, and the fact that I knew I'd never see this girl again, caused me to put ethics aside and we were soon making out in my room. Minutes later, we were naked on the bed, rutting like a couple of dogs. I felt horrible the next day and kept my infidelity a secret. Imagine my surprise when my girlfriend eventually confessed that she had cheated on me while I was away. I was hurt—hypocrite that I was—but it was a sign that our relationship was not strong and we split up some time later. I have since found greater pleasure through women who did not want a single partner.

Rhiannon and I napped for almost an hour, then got up and made supper. We still had some time before our next activity, and I delighted in keeping it secret from her. “Your last night will a good one, trust me,” I said.