It Was Awkward When Her Son’s Friend Found Out About Her New Job

Thanks to the recession, my husband lost his high-paying job. He landed a new job, but it involved a big pay cut and way more hours—and we’d just bought a house and our youngest had just started college. There was no choice but for me to go back to work for the first time in twenty years. And since I’d only held menial jobs like waitressing, even with my income things looked grim.

One afternoon I was bemoaning my situation to my friend Rita. When I finished, she looked me over carefully, then said she knew what I meant about needing extra cash and in fact had taken a part-time job herself, one that was quite lucrative. She said there might be openings if I was interested.

I asked what the job was. She stunned me by saying she worked as an escort! I couldn’t believe it, especially since Rita was married, like me. I stammered that I couldn’t be some kind of prostitute. She said the business was very professional, with none of the girls doing anything they didn’t want to. If all I wanted was to be eye candy on the arm of an out-of-town businessman at a charity event, that was fine. Then she told me the going rate for one night, and I was shocked. It was a lot more than I’d make as a waitress at some bar.

I came down to earth and pointed out there was no way anyone would want a forty-four-year-old escort. Rita said there was actually a great demand for “cougars”; her employer had told his girls to be on the lookout for any. She said that considering my looks and the shape I was in, he’d probably hire me on the spot.

Before I knew it, I had agreed to hear her boss’s pitch, and Rita insisted we do it now, before I lost my nerve (or regained my senses?). So she called him and arranged a meeting for that very day. I expected to meet the guy in some dive in a seedy part of town. Instead we pulled into the driveway of a nice house in an upscale neighborhood.

We were greeted by a handsome, charming gentleman. Grayson led us inside and offered us a drink. After some polite conversation, he explained things just the way Rita had, adding that as attractive as I was, I would be requested a great deal. He offered even more money than Rita had spoken about!

I knew I shouldn’t accept, but we needed the money, and I could make so much. And where was the harm in going on a date? It was like acting, which I’d done in school; it was just an unusual role.

I accepted the offer, making sure that Grayson contracted me only through my cell phone, since I knew my husband wouldn’t approve, despite our financial woes. He said he understood and would of course be discreet. He promised to contact me with specifics later.

As Rita and I left, I was still in disbelief. Then she pointed out that while the standard rate was nice, if I agreed to provide “full services,” I could really rake in some cash, and she quoted me a figure that made my jaw drop. I asked her if she did such things. She played with her diamond earrings and asked where I thought they came from.

I said that sort of thing wasn’t for me, though not as forcefully as I should have. My thoughts had turned to what I could buy with that kind of money. Rita said that if I did reconsider, to let Grayson know so he could plan for the higher rate.

Rita dropped me off at home, and I worked on a cover story for my husband. I decided to say I’d found a job across town waitressing in a biker bar. Since he disliked bikers and bars, it was unthinkable that he’d ever “drop by.” I thought he might object to me working in such a place, but he just grumbled about how it was about time I pitched in! I wasn’t thrilled with his attitude and decided that if he was okay with my being felt up by bikers, he shouldn’t have any problem with my “dates” doing the same.

I was a little tense for my first few dates, but soon I was relaxing and actually starting to enjoy myself. It was nice being given the attention I hadn’t gotten from my husband in years. What really surprised me, though, were the clients. While some were my age or older, most were younger, some considerably so. In several cases I was practically old enough to be the guy’s mother! The younger fellows tended to come on to me a lot more, and to my surprise I enjoyed them the most. I knew that I should be feeling guilty, but I didn’t manage it. I was enjoying myself too much.

After a month on the job I got an offer slightly different from the norm. One of two girls hired for a bachelor party had canceled at the last minute, and Grayson asked if I wouldn’t mind filling in, at double my normal rate! The other girl would be offering “full service” to the groom-to-be; my job would simply be to circulate in a skimpy waitress outfit and serve drinks to the guys. He warned me I’d get felt up a lot, but added I’d get lots of tips—the more flirty I was, the better they’d be. Since my dates tended to do that sort of thing anyway, I figured why not?

When I got there I was given the uniform, which was even more risqué than I’d imagined. The neckline was cut so low that my breasts would be practically falling out, plus the skirt was so high, my ass was virtually on display. Still, I put it on.

I felt nearly naked when I went out and served drinks to the guys. Almost from the start they were running their hands along my legs. Some patted my ass as I served drinks. But they all tipped generously. And to my surprise, I found myself turned-on at the sexy contact!

I’d been there for a while when a voice gasped, “Mrs. M?” I jerked at hearing my name and turned to see a young man in his early twenties. My heart froze when I recognized Robbie, a longtime friend of my oldest son, whom he was still in contact with! I cursed my luck and tried to think fast, knowing that Robbie could blow it all with one errant word to, well, anyone.

There was only one thing I could think of that was all but guaranteed to keep his mouth shut. Giving him a sultry look, I walked over and said it was wonderful to see him after so long. I flirted heavily while I explained my financial situation and stressed how much I would appreciate his discretion about my new job.

Once he collected himself, Robbie asked, “Just how appreciative?” I ran my hand meaningfully over his crotch and said “very,” then led him to the nearest bathroom, which thankfully was empty. We locked the door, and I dropped to my knees and went for his pants. I was so caught up in securing his silence, I never considered that I was cheating on my husband for the first time.

I lowered his pants and was treated to the first new cock I had seen in more than twenty years. It was as long as my husband’s and much thicker, so much so that I had trouble wrapping my hand around it. Suddenly all I could think about was this cock, rather than my impending infidelity. I wrapped my lips around the head and stretched my jaws to the limit, then began sucking wildly. It was like the first time I gave a blowjob, I was so eager. My head bobbed up and down, and I made slurping noises as I drooled all over it. I was so aroused, I felt myself get wet.

Robbie was really wired and lasted only a couple of minutes before unleashing a gusher down my throat. His youthful payload, bigger than anything my husband managed, lasted forever! There was so much that some ended up trickling down my chin and onto the top of my generously displayed cleavage.

I actually felt a bit disappointed when Robbie’s rod finally stopped pulsing in my mouth. I released it, stood up, and went to the mirror over the sink. I knew it wouldn’t do to strut around with semen decorating my breasts, so I started cleaning them off. I had just finished when Robbie bent me over the sink, reached up under my skirt, and ripped my panties clean off!

I was so startled that I froze, but only for a moment. I felt the head of his still-hard cock penetrate me, and I groaned loudly as his shaft stretched me in a way no cock ever had. “Damn, Mrs. M,” he said. “You’ve got one tight pussy.” This didn’t stop him from sinking more of his cock in me. But since I was pretty wet, he was able to muscle himself in.

Once that thick thing was all the way in, did it ever feel good! Of course that was nothing compared with when he began thrusting in and out of me. It was slow going at first, given how tight I was squeezing him, but my juices kept flowing, and soon I was loose enough for him to give it to me in a rhythm of steady thrusts.

The next thing I knew, I was coming hard—real hard. Robbie kept pounding away through my orgasm, saying how he’d wanted to fuck me as far back as he remembered, and I was better than he had dreamed! The hot talk fired me up, and I came again, with Robbie following hot on my heels, filling me with a second sizable load. When he pulled out, I felt it trickling down my leg.

I was just starting to collect my wits when Robbie unlocked the door and we exited—to a long line of irate guys waiting. When they saw me, they figured out what had happened and congratulated Robbie. They took the liberty of feeling me up as I walked down the hall past them, many of them grabbing at my now-bare bottom.

I was still in a sort of daze as I went back to the main room. I had missed a lot. My coworker had jumped out of the cake and stripped and was now fucking the groom while everybody hooted and hollered. The crowd was now really rowdy, and I got felt up more than ever. When some guys discovered I wasn’t wearing panties, they got bold and finger-fucked me while I served them, tipping well for the privilege. By the time the night was over, I had made more in tips than I got paid for the night up front.

Back home, I had some soul-searching to do. I tried feeling guilty, tried saying that I had done it only to keep Robbie’s mouth shut. But all I could think about was his gorgeous cock in my pussy and being all but molested by a roomful of strangers—and how much I had enjoyed it!

Every night I had dreams of having even more sex with Robbie, as well as some of the other guys I’d met. I was a horny mess. Business went on as usual until the following week. Since one of my jobs was a date for a wedding, I might have put two and two together, but I didn’t until Robbie showed up, all smiles, to pick me up in his car! I was nothing but nervous. I knew from the look in his eye what he was expecting, and I knew I should have laid down ground rules, but all I could think of while we made small talk on the way to the chapel was his gorgeous cock.

At the chapel more than a few eyebrows were raised—some by our age difference, others from guys who recognized me from the bachelor party. After the wedding we went to the reception, where drinks flowed and things got a little wild. Robbie was all over me on the dance floor, fondling me like crazy in front of everyone. After a few dances some of the other guys asked to cut in, most of them party guests. They were free with their hands in a way that would have gotten them slapped if I weren’t so fucking turned-on.

After dancing and drinking, Robbie suggested we go to the hotel across the street, where he’d booked a room. I didn’t hesitate. When we had barely made it past the threshold, he grabbed me and unleashed a kiss that made me weak in the knees. His hot hands were all over me, unzipping my dress, then taking care of my bra and panties, leaving me naked before him.

Then he picked me up like I was a blushing bride, laid me on the bed, and said, “Now that we’ve got time, I’m going to take you in every way I’ve ever dreamed.” He started things off by spreading my legs and eating me out. God, his tongue felt fantastic lapping away at my loins!

Eventually he removed his own clothes, displaying a fit frame to go with that glorious big fat cock. Keeping my legs spread, he shoved the entire shaft in! While I writhed on the bed, he began fucking me. After a while he draped my legs over his shoulders and pounded my pussy like there was no tomorrow. He leaned forward until my ankles were pinned on either side of my head and fucked me even harder until we climaxed at the same time.

While we rested, there was a knock on the door. To my shock Robbie called out, “Come in,” and in walked five of the wedding guests, guys about his age. He explained that at the bachelor party the guys agreed that while the girl who fucked the groom was attractive, I was much hotter. He figured that since I was so eager for a good fucking, I wouldn’t mind strutting my stuff for the other guys, too.

I was running so hot, more cocks sounded like just the thing, so I told them to show me what they had. Over the next few hours I discovered what getting gangbanged is all about, getting double stuffed constantly, with replacements always ready whenever one of the guys popped. By the time they finished, I was a mess and could barely walk straight, but it was the best sexual experience of my life.

I became a full-service escort and now make more than my husband, though I have to hide most of it from him since no waitress pulls in what I do. And to think, I can thank the recession for opening up the job opportunity of a lifetime!

—Name and address withheld