Where it happened: Beach Condo
Langauge: English
Sex: Male
Rating: 5
Category: Straight
Converting a Co-Worker
My first man on man sex.
I’ve been wearing panties for years now, and have never shared my secret. I had to travel to a job site 400 miles from home, and stay maybe up to a week. On the plus side, I could stay in my friend’s beach condo during the stay. Even if it were in January, the hot tub after a long day’s work would feel just right.
A bigger plus is that I could wear my panties all day and night.
My boss suggested that he needed me back in three days, not a week, so he told me that “Dave” would go with me to speed things up. Drat!
After the first day of work there, we made it to the condo; I said I was headed to the hot tub, and asked if he wanted to join me. Then I remembered that I hadn’t packed any swim trunks, as I had planned to be alone. He told me that he hadn’t packed any trunks, either as it was 30 degrees outside. I said I hadn’t either, but was going anyway, and he was welcome to join me naked, if he felt like it.
He came out onto the balcony in just his Jockey shorts. Old, worn, baggy ol’ Jockey shorts.
When he stripped, and got in, I couldn’t help but notice what a nice looking penis he had.
We sat and talked for a while, and seeing his Jockey shorts laying on the table, I suggested it might be time to get some new ones. He laughed and said “Yeah. I’ll tell the wife to get some. Maybe she’ll get me some like yours. Where do you get those?”
He had seen mine lying on the bed, by my pants, I guess.
“You like those?” I asked.
“Well they look better than mine. What kind are they?” he asked.
Well, here goes. Heart pounding fast, I said they were Victoria’s Secrets.
“They make men’s stuff, too?” he asked.
Not too bright, I thought, but that told me he was pretty much un-aware of my fetish.
“No, they’re women’s panties. I just like the feel and fit. I don’t like my hardware bouncing all over the place. I like them nice and snug.”
We sat there what seemed like an eternity. Then he asked, ”What does your wife think?”
“She would rather I wear ‘men’s underwear, but she’s more or less ok with it, “ I responded.
“Hey, that’s cool with me. I kind of thought they were different today when I saw them when you were reaching over that guardrail today. I never have tried anything like that.”
I couldn’t help but notice that he was getting a woodie as we talked.
“Well, “I said, “I’ve got several pairs with me if you want to try some on.”
Damn, I can’t believe I am saying this.
“Now?” he said.
“Sure”.
We both got up and out, and went to my bedroom. I got him out a pair of really nice silky white ones, and in handing them to him, watched him focus on them with a child’s amazement.
I’ve never had any kind of sex with a man, up until this trip, that is.
“Let’s dry you off a little better, so as not to soak my panties, ok?” I said.
“Ok.”
I took his towel and started at his feet, and by the time I got to his knees, he was rock hard. Eight inches of him.
As he tried on my panties, it was obvious that with his hard dick, they wouldn’t fit all that well. He said maybe he should wait for it to go down. Now or never!
I told him I could speed things up a bit, if he wanted.
“I guess so,” he said, hesitating.
I was on my knees so fast, hands trembling; I reached for his balls with one hand, and his dick with the other. I felt his knees tremble. We lay back on the bed without missing a beat. He must have liked it, as it only look him a minute to fill my mouth with his cum.
“Damn, that was nice,” he said, “could you teach that to my wife?”
“Actually, you’re my first blowjob,” I said. “I don’t normally do this, but with being far from home, I don’t know what came over me.”
“No, really. That was great!” he said, as I ran my hand all over him. “If that’s your first time, how come you’re so good?”
I told him that it must be because I know what I like, and what a penis likes, too.
“Can I try on you after a little while?”
Duh!
He spent the next fifteen minutes wandering around the condo looking at himself in the mirror, at his newfound panties.
“Yes,“ he said, “I gotta get me some of these.”
“Why don’t you wear those tomorrow at work?” I offered. “Nobody will know but you and me.”
The jobsite was left to just us, as the place was closed for the winter, so it was just he and I for the next few days.
The next day, all day, I couldn’t help but notice his woodie. All day. During lunch, I asked him out loud, (nobody around but he and I), “Can I suck you off again?”
It felt so good to say that out loud. I gave me a tingle just saying it. I un-zipped his pants, undid his belt, and pulled his pants down to his ankles. Leaving him there in his new panties. Then they too had to go. With a butt cheek in each hand, I sucked him off again.
I pulled up his panties, and rubbed around a little, then pulled up his pants, zipped, buckled his belt, and back to work we went.
That night when we got to the condo, he wasn’t two feet inside the door when he was down to just his panties. He seems to like this more than I do. But then again I remember my first time, as we all do.
“Shower time”, I called from the bathroom.
He came in and stepped right into the shower still wearing his panties. Smiling.
“What you got in store for tonight?” he asked.
I responded with, “Like I’ve got this all planned out? I don’t know. I’m just winging it.”
I lathered him up real good, saving his groin for last, and when I got there, I was afraid he might break some of the tiles with his dick, he was so hard.
I dropped the soap bar and he said, “Oh, I get it.” He sure did. Both of us, covered in suds, taking turns pounding each other in the butt. We did this until we ran out of hot water! What a thrill. My first encounter with a man and what a great one. And I was worried about him seeing my panties!
Out of the shower, we went to the hot tub and talked for hours. All the while playing with each other’s dicks.
Three days of this and what a memory!
Back at work, everything was back to normal. Really normal. I was wondering if he had any regrets, or felt guilty once back with his wife. I found out when I announced that I was going to a service conference in a month and had one more opening.
“Would anybody like to attend a three day service school in Washington State next month?” I asked my service guys at coffee break.
He beamed.
I knew.
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