Richard is a particularly intelligent and arousing email partner.
In our play online he liked to dress in women's underwear, as Cami, and takes direction, getting up in the middle of the night to pull his cock back between his legs commanded look in the mirror at his smooth "pussy", shaving it for me.
Taking to the next level I had instructed him to spank it and email me immediately, and took this erotic thought into the bedroom, mounting my wife Mel, thinking of him with cock in hand.
He was on the west coast, two hours difference in the Bay area, he shared with me that he liked to go to San Diego and meet men there, painting me a picture of his time taking cock down his throat in hotel rooms, on beaches and street alleys.
"Yours would fit nicely there," Richard would tell me, enticing another hot trans story out of me, taking him in public, forcing his mouth on my cock in a restaurant.
I told him our family travelled to San Diego four years ago. When my wife Mel and I thought of booking a flight there for a long weekend in June, I wondered.
Fast forward four months later and my mind was still wondering.
I stopped email stories or directions and neither of us were into phone, cam or sending pictures, so we lost contact.
That was until the week before our flight to San Diego.
"What would you say if I told you I would be on your coast in seven days." My email simply read. I doubted anything could or would happen, but the thought of going for a run and meeting up, or a random encounter, made my cock swell.
I checked back in an hour and my email response was, "Oh HELL YA! How do you propose we get this done?"
He was serious. We went back and forth for five days, I laid out our itinerary, my thoughts and he countered with ideas and locations.
We'd never exchanged photos, we were both in decent shape, having been runners for years and I worked out 2-3 times a week. I was taller (6'2" to 5'9") and he was submissive where as I could play either role. We got on a messenger app that didn't require us to give our personal information and the plan was finalized.
I would land out there, get to our rental house and make contact. We had dinner planned and he would be there alone. I would be wearing a "Masters" polo, blue with a pattern. At a point I felt comfortable I'd go to the bathroom, he would walk in and we'd kiss, and that would be it for the introduction.
Secondly, if either felt they wanted out at this point, we'd message that, otherwise the next morning I would go for a five mile run (that's what I would say) instead going to a nearby motel 1/2 mile down the road from our rental.
Using the messenger, I'd signal when I'd was getting there.
The last two days of our trip were not planned, and if that's all we did, that was more than anything I could have dreamed, otherwise we'd try to set something up for the last two days.
I got on the plane nervous, almost talking myself into backing out, Mel looked beautiful and we had fucked just the night before. I thought about the 'escape' clause and using the messenger when we landed.
I had gone to the bathroom in flight, and when I returned Mel had gotten me a drink. A free promotion for getting a couple credit cards, something she was good at finding. We downed one and got the second, the effects without eating making my apprehension for meeting Dan drift away and now I was looking forward to the meeting.
I'd never kissed a man, having written and chatted about doing so, hard, stroking and even cumming while chatting about dancing erotically with my sissy boi Cami. Richard promised to wear panties and I was planning on sliding my hands in his shorts to double check.
We landed, got our keys to the house so Mel and I headed to the beach before getting into the house. We continued to drink and even held hands walking on the beach. We finally made our way there, took a nap and then got ready for dinner.
"You're looking great tonight," Mel said, my Master's polo showing the weight I'd lost and the muscle definition. I put product in my hair, short as it is at 55 still holding firm since I was in my early 20s, salt and pepper, though still more pepper. I had new shorts, the ones that show off a man's ass better, and a nice Keen sandels, my calves are a little small, though my legs are pretty nice.
We walked down to Harry's SeaShack, a nice open air restaurant that wasn't fancy but well run and my wife had researched that it had a lot of good reviews and awards. We wanted seafood by the sea, so a perfect first spot.
Richard had detailed where the upper bar was and looked like, and that he'd be in a Hawaiian shirt, floppy hat and shorts.
My cock swelled when we entered.
The street entrance went into the upper bar area and I spotted him just two steps into the establishment. I squeezed my wife's hand and let go, heading to the host stand, and we were given a buzzer to wait for our table. I got rock hard with my next thought - "Hey Mel, let's go over a get a drink" and made our way to the bar, in the direction of Richard.
"Mind if we sit here," I said to him, looking directly at his face, it was pleasing, his eyes turned and saw the shirt. I extended my hand, "Donnie and this is my wife Mel."
"Donnie, glad to meet you," he shook my hand and he nodded to Mel, who nodded back already sitting down and ordering drinks for us.
"I'm heading to the bathroom," Mel said, leaving me alone with Richard.
"They're up the steps over there," Richard pointed Mel and she moved in that direction.
"You're ballsy.." Richard said, looking forward.
"Are you wearing the panties I instructed you to wear?"
"Jesus Christ, this is going to be fun," Richard said, my drinks laid in front of me.
"You got it, just wait I've had another thought," I said, remembering my wife's desire to go to 'off the beaten path' on vacation. Including into town in Mexico.
"Hey, here's your drink," I said to her when she came back, my tone leading into a statement getting her attention. "Richard here is really familiar with the area and just stopped in for a drink. Let's have him sit with us and pick his brain."
"That sounds amazing!" Mel said excitedly. "If you don't mind, unless you have somewhere to be."
"I can maybe have an appetizer and you can tell me what you're looking for exactly," He said. "You've started with one of my top recommendations in eating here."
We chatted and got our table, adding a third wasn't a problem and we ordered. Richard was honest completely and so were we about who we were and what we did. He talked about his wife, who suffered from several afflictions that kept her around the house.
"I have too much free time that's for sure," He said, starting into his appetizer. "Tell me what you're thinking and I'll give you two or three places."
