One of my company’s oldest customers called to say he’d sold out to a couple of enterprising young men and was retiring to Florida. It didn’t shock me, since Brian’s wife had passed away awhile back. He said he would like to introduce me to the new owners in hopes we could continue doing business.
I talked it over with my boss, who agreed it was an account worth trying to save. I booked a flight and managed to arrange two days’ worth of meetings with other clients and potential clients in the area before my meeting at Brian’s company.
It was a late-afternoon flight, scheduled so I could get a decent night’s sleep before that first early-morning meeting. What with dealing with one thing and another before heading for the airport, I didn’t eat anything all day, and by the time I arrived at my hotel I was starving. After checking in, I had the presence of mind to order room service. I ate in my room and slept well.
For two days I focused on my meetings, which were all incredibly productive. After my last appointment on the second day, while I was relaxing at the hotel bar waiting for a table in the dining room, I met a young marine named Peter, in town on some kind of recruiting tour and departing the next morning. When his table was ready, he asked if I would join him, and I accepted on condition that he let me pick up the check. I said it was the least I could do for a man serving our country.
Needless to say our evening didn’t end in the dinning room. By nine we were in my room, where Peter said he’d always dreamed of making love to an older woman, and if he wasn’t mistaken, he thought I was about to make his dream come true. I told him I was a married woman away from home for the week, and I was lonely and could make his dream come true, but he had to be careful not to leave any marks on me.
I began to take my clothes off, and Peter watched wide-eyed, not missing a thing. I was showing off—I’m damn proud of my 40-year-old body. (It takes a lot of work to keep it in this shape!) So I was gratified to hear him gasp when I slipped off my bra. At the same time, I had to wonder how much action this boy had had, especially unexpected given how cute he was. Yes, he seemed awfully young, but even so—
As I hooked my thumbs in my panties the phone rang, causing Peter to jump about a foot in the air. It was my husband calling to say good night. I told him how well the day’s meetings had gone, and said I was in bed reading before I went to sleep. I think he bought it.
After hanging up, I turned to find Peter about to cut and run, afraid we’d been busted. I told him not to worry, that my husband was 500 miles away and we wouldn’t be disturbed again. While I peeled off my panties, he fumbled his way out of his clothes. When he dropped his shorts, his drill sergeant would have been proud of how straight and tall his tool stood at attention. I figured his sturdy five-and-a-half-inch weapon should be enough to fulfill my needs. Given his age, I was pretty sure his gun was a fully loaded semi-automatic that could fire repeated loads.
I turned down the bed and crawled near the center. I rolled over on my back and said, “Let me help you put that big throbbing tool at ease, general.” He wasn’t taking his eyes off my cunt and meanwhile was trying unsuccessfully to roll a condom on inside out. I told him I didn’t want him using a rubber, that I liked it bareback. He clambered to position himself between my legs and lowered himself frantically toward my smoldering snatch. He wasn’t anywhere near his target when his gun went off, scattering spunk from my neck to my pussy.
He was visibly upset when the last drops of jism dripped onto my cunt and his erection began to wilt. Suddenly he collapsed on top of me, and I had a feeling he was crying! I held him with my left arm while working the right between our come-smeared bodies and grasping his limp cock. As I hoped, it became hard again almost as quickly as it had become soft. I wiggled my hips and fed him into my pussy, only to feel him throb as he came again, inside me.
This time he didn’t lose his erection, but remained hard inside me. If he’d been crying, he wasn’t anymore. Now he pumped his hips slowly while whispering, “Ohmygod, that feels incredible. You’re so beautiful, and I’m inside you, and we’re fucking! I’m fucking you!” Followed by: “Oh damn, I can’t stop it, I’m coming again!”
I felt his cock jerk again as it released another load—not a large one, but still, it was his third in hardly any time at all! Then it softened and slithered out, followed by a small river of his come, which trickled down the crack of my ass.
He looked at me and said, “You probably guessed this was the first time I’ve ever gotten it into a woman’s box. It’s always gone off before I could manage that. Thank you so much. I will never forget you.
I held him and comforted him. I told him every one of us has to lose our virginity sometime, after all, and I considered myself fortunate to have done the job for a hot hunk like him. I added, “Nobody was more scared than I was when I lost my virginity to an older man, but once he popped my cherry I fucked him all night. And now I want you to fuck me all night. I’d like to be the best first piece of ass any young man ever had.”
My handsome young marine did fuck me all night, allowing me very little sleep, until he had to rush out to catch up with the rest of his recruiting team. I called the desk and asked them to hold off cleaning my room until afternoon, and to wake me at 11. Then I slept until the call came.
I got to Brian’s plant—or rather his former plant—right on time that afternoon and met the new owners, Ray and Louis, who assured me that at Brian’s recommendation they had every hope of continuing to give us their business. We had a brief discussion of terms, and to my surprise they said they were sold and ready to sign as soon as I could get them a contract!
This seemed like a good time to get my boss on the phone. He was delighted, and said he could overnight the contract—would I mind staying over another night? I said of course, and after hanging up told Ray and Louis I would have the contract for them in the morning. That seemed to please them, and they said they were looking forward to it.
I excused myself to make a few calls. The hotel had no trouble holding my room for the extra night, and the airline rebooked my flight for the following afternoon. My husband sounded disappointed but understanding. “At least it’s been a productive trip,” he said.
“Are you kidding?” I said. “I’ve done six months’ worth of business in these few days. I promise to make it up to you when I get home.”
When I finished, I found Brian all by himself, offering Ray and Louis’s apologies for having to go on to another meeting but saying they looked forward to seeing me again in the morning. Sounding wistful, Brian said he would miss having meetings to have to go to.
“Now, Brian,” I said, “if anyone’s earned the right to blow off all future meetings, it’s you. Look what you’ve built here, and in what excellent hands you’re leaving it. Speaking of which, how do I ever thank you for whatever you did to sell Ray and Louis on my company?”
“No need, sweetie,” he said. “They’re good boys, and smart. Smart enough to understand how well you’ve done for us. But if you’d like to humor an old man, you might have dinner with me.”
“Shit, Brian,” I said, then caught myself. “Sorry about my language. It’s just that I’m wiped out from this trip. I was planning to just go back to the hotel and crash.”
“Will you still be around tomorrow?”he asked. I said I was flying out immediately after meeting Ray and Louis.
I felt as bad as Brian did. We’d done business for 19 years. “Shit,” I said, rallying, “let me just take a nap, and pick me up at the hotel at six. Well, make it seven.”
Sure enough, when Brian called up from the lobby at seven on the dot (he always had a thing about punctuality!), I was dressed and feeling okay—and glad we had managed to salvage the dinner. He was a sweetheart as well as a good businessman. I was going to miss him.
He said the hotel dining room was fine with him, but again we had to wait for a table. We each had a couple of cocktails while we waited. I was glad not to have to get through dinner sober.
We had an outstanding time, celebrating the history of our business relationship and focusing on Brian’s anticipation of retirement. Afterward he insisted on seeing me up to my room. At the door I turned to say good night and was caught off guard when he embraced me and laid a kiss on my lips, one of the most passionate I ever had. I realized that his hand was under my dress massaging my pussy through my skimpy panties.
When our lips parted, I whispered, “Please don’t fuck me out here in the hall. Let me unlock the door.” Minutes later we tumbled into bed. I was naked, but Brian still had his boxers on as he dived down and ate me out more masterfully than any man had ever done. His tongue was lightning fast, long and teasing.
He asked if I was all right, and I whispered, “I want you to fuck me, Brian.”
He moved between my legs as I lifted and spread them to receive him. His cock was even smaller than Peter the marine’s, but the knobby head really stimulated the mouth of my vagina, and I quickly felt my arousal building. He fucked me with short, rapid strokes for 20, maybe 30 minutes, until I exploded and he did too.
In the morning I woke him by sucking his cock, trying to give him as good as he’d given me. He held my head as he spewed in my mouth. He gave me a repeat performance, then dressed and sped home to change for the meeting with Ray and Louis.
I picked up the overnight envelope at the desk and met Brian there. The meeting went off without a hitch, and so did my return trip, during which I pondered the range of male experience levels I experienced on this triumphant trip. At home my husband greeted me with champagne, and no potentially awkward questions (our version of “don’t ask, don’t tell”). I was relieved.
—T.E., Minneapolis, Minnesota