MWM Bisexual Musings Ch. 02

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."

We liked kayaking, and was wondering about the tours in the bay and into the cove. We golfed and wanted to hit Torrey Pines, or hang glide off of that spot. Mel wanted to hit the shopping areas and then night life we wanted to hit somewhere that wasn't too touristy one night.

"If you don't have a reservation already, I doubt Torrey Pines is available," Richard said, getting my attention for a possible day alone with him. "Count's lair" or "The Rave" are older, but packed places, still getting some of the younger crowd."

He rattled off lunch spots after Mel asked and he had several recommendations.

"I read earlier that there were cancellations for Torrey Pines and to call before 8 am. and before Noon. That may be our best bet." I said, Richard looking at me like is that right?

We got all the information and he gave Mel his card with his email and cellphone on it if she "Had any questions."

"Excuse me, I'd better get going," He said, looking at me. "I'm going to hit the head first."

"Yeah, I've got to go as well."

"You gave her your card??" I asked walking behind him up the stairs.

"Shit, she already knew enough, relax..."

The bathroom was larger, but the stairs could be used to see anyone coming upstairs, the roof only used at night as a bar, so there wasn't anyone but workers up there.

Two people poured out of the bathroom, I went in and saw it empty, opened the door and before it shut I pulled Richard to me, slid my hand down his back and then his shorts as my lips covered his.

"MMmmpfft, ohhh" Richard sighed, my lips moving over his, then my tongue going deep. "OHhfhhfhhftt"

His hands went to my face, I leant into him pushing him to the other side of the stalls, if the door opened we could break and just act like we were finishing.

"I want your cock so bad," Richard said, my hands rubbing his chest and down over his cock. "Shit..."

He reached down my shorts, felt how hard it was, the door opened and we broke.

My heart was racing, a large African-American male looked at us, I left and Richard went down inside a stall. He left us alone and I headed to Mel.

"Well that was lucky running into a local light that," Mel said.

"Yes it was, Dear," I agreed and we started into our entrees.

I took the excitement of the meet up when we got to the rental from lunch and immediately got Mel naked, into the hot tub and riding my cock there. We ended the night just strolling the neighborhood and down to the strip of shops and bars by the beach and had a couple drinks. Our first short day/night of this trip ended around Midnight just drifting off to sleep.

Checking my messages, Richard had secured room #23 at the "Palace Beach", Mel and I walked past it, my cock bristling hard thinking of the next morning. My alarm was set for 6:30 a.m. and we agreed I'd be knocking on the door at 7 a.m., it would give us a good hour.

'Cami wants that dick jamming the back of her throat,' the message read, Richard talking about his sissy persona that was going to be greeting me at the door.

It was late enough that I feel asleep, the alarm startling me the next morning, my mind immediately shifted to the experience I was about to have that I had never.

I had sucked cock, but had never had mine sucked.

I was manipulated close to the point of abuse, though I enjoyed it in the moment, looking back it was a power gradient that controlled me. His cock was beautiful and I submitted to him for almost a year.

Online I had found my dominant voice, while the heterosexual side of my bi tendencies carried me through many good relationships with women, into marriage, children and now nearing retirement. Cock was always on my mind, but didn't cloud my enjoyment of all sex.

That morning I stretched and got jogging, the sun was up on the horizon, the morning wasn't cool, but wasn't warm either. It was just 1/2 mile, but that was better than nothing in my mind, getting a mile going both ways was my end goal. Part of me was bummed I wasn't going to be running five miles, the smell of the water, the sound of the ocean, it really is a highlight for me jogging in these places.

I approached Palace Beach, looked up at the second floor and made my way to the steps. I grew hard with each movement upwards towards room #23. The jog warmed me up, but didn't have a sweat going when I approached, looked at my watch that said 6:59 and waited until it changed and read '7:00'.

I knocked on the door.

In our correspondences, I indicated I wanted to meet Cami that morning and Richard relayed he didn't feel good about being in drag in public. I requested she wear in a nice summer dress with the appropriate underwear, and didn't need make up. The door opened and Cami looked out at me, a sunflower dress on, push-up bra, showing off a smooth chest.

"Come in please..."

The door opened wider and shut behind me, the shades just had the sheer white insides so the sun was illuminating the room. There was that moment of awkward silence, in our emails I knew I could just rush her, rip her panties off and have her or demand she get on her knees. Meeting Richard yesterday I concluded I would wait for at least 30 minutes before engaging in the copious ending we both wanted.

"Cami, great to meet you finally." I said, holding my hand out, she shaking it a little confused. "Donnie..."

She smiled, her eyes down and not really making contact with mine, she was not sure of my intentions and let me lead. Jogging there I pictured just doing a live role-play, conjuring the talk and ideas written in so many chats, just live in person.

"Cami, tell me how does a high school valedictorian with a scholarship to USC become the highest paid call girl on the west coast?"

She looked up slowly, the words absorbed and figuring out what I was doing.

"I grew to like cock right away on campus, really," Cami said, moving around thinking, talking. "You first do it, you know, suck dick when you didn't want to become pregnant. I'm rambling I know."

"Relax sweetheart, we have time..."

"I'd study at the library and the first night...the very first night...a young man I had met in my class, at the end of the night, was very forward," Cami said. "He complimented me and said how gorgeous my shape was...then just out of no where, he asked. 'Hey, can you come up to my dorm and give me head?'"

"What did you do?"

Cami looked at me disappointed, because I knew the answer.

"I sucked his cock, silly," She said, and ran her hand over my shoulders, began to massage them. "We had this little routine about 2-3 times a week, and I got really good that first semester."

"Everyone fucks and sucks on campus in college, how did you parlay that into a six figure sex operation?"

"Word gets out..." She said, her hands magically kneading my muscles, I turned to look up at her, and without hesitation, removed my shirt. "Oooo, I like that."

Her hands went down to my nipples and back.

"First it was his roommate, who was a manager on the football team," she said. "And that got me to a player's party. I had started taking birth control, while I wasn't a virgin I didn't plan on being a slut either."

She moved to my front, slid a leg over mine, and sat down in my lap, her hands around my neck.

"Apparently the running back I went down on and who fucked me from behind was quite impressed, and left me a $100 tip in my purse. Word got around and then I started to get around at $100 a pop."

"Mmmmm, that feels good," I moaned, closing my eyes while she ground on my swelling cock, her dress coming up so my hands went to the edges and pulled it up and over her head, it fell to the ground. Her yellow bra and panties combo was divine, hips moving back and forth. My lips lingered near hers, while she continued in soft, breathy words.

"The running back got drafted, and he had a lot of disposable cash. He loved the university, so whenever he was in town with his posse, I was holed up in a room somewhere, giving them exactly what they wanted." She said and kept gong. "I soon had to recruit a girlfriend or two, and we created 'USC Escorts'..."

"Ohhhh," I said, the imagery of athletes fucking a group of co-eds, her hands on my shoulders, Cami executed the role-play perfectly and I dove in for the kiss.

I stood up, six inches taller than her I pushed my face down, her hands were on my shorts and spandex and soon had my cock out. Kissing her way down my stomach, she held my cock in her hands and before I knew it, was swallowing it, it's length perfect and it's diameter not too intrusive. Cami was experienced, her hand under my balls, fingers playing with my taint and hole.

"Ooooo, Daddy likes that Cami..." I moaned, eyes closed, numb from having came twice in the last three days. I held her head and began to pump at my pace, holding her tight on my cock, releasing and repeating. In the moment, still wearing lingerie with the spirit of the role-play still there, the difference between jamming my cock in a woman versus 'Cami' was minimal.

The absurd reality that we set this up and were in the throws of an affair with our wives close by, intoxicatingly dirty.

I pulled out of his mouth, sensing I needed something more.

"Dance for me Cami," I commanded, story telling time over and now I was going to give her what she wanted. She complied, closing her eyes and swirling and moving to an imaginary song filling her mind. "Now strip!"

Cami didn't change a beat and swirled around, showing me her ass, swinging it around, then pulling her panties down, her man-pussy there, unsnapped her bra, and that hit the floor. Per my request, a jar of lube was close by and I grabbed it, took control of Cami dancing, forcing her to face away from me.

"Ohhhh Donnie YES!" she approved of my motions.

I lubricated her hole, my cock and holding her hips I pushed forward.

"OHHH DONNIE! she exclaimed I slid deep inside, her body folding at the hips, bending a little, I moved her forward where there was an ottoman there her hands braced on. I pushed balls deep. "YESS! OHHH FUCK YES!"

My movements weren't well coordinated, having limited giving anal experience, I pushed her forward onto the ottoman then pulled her to the floor and I bucked her from behind. I laid on her back, kissing her neck and began to fuck her rapidly.

"OH GOD YES!" she kept crying out, I pinched her nipples and did reach down and stroke her cock, hard and similar size to mine. "Fill me DONNIE! I want to feel you running inside of me."

The tightness of his hole brought the surge and it was just a few minutes later that I thrust forward and released what I had.

"OHHH YES! Mmmmmmm"

I pulled out and sat back, looking at Cami turning around

"Jack it for me till you cum!" I said, she looked confused. "Do it!"

She reached down for her cock, no remnants of a woman left on her, but I still saw Cami before me while she used her precum and the excess lubrication and stroked fast.

"Ohhhhh!" she exclaimed, eyes closed, cum flying out of her cock, it was tilted back and onto her shaft, balls and some up towards her stomach.

I had experience here, I moved forward and took her receding cock in my mouth and cleaned her cum, sucking everything, her hands in my hair. I finished, we kissed and petted each other for the next 15 minutes, holding each other in the middle of the room.

"Do you golf?" I asked.

"No, never have"

"I can get us both on Torrey Pines tomorrow, regardless. Mel can shop," I said I was getting dressed, he stayed there naked on the floor. A moment later I was kissing her and saying good bye.

I ran back to the rental, hit the shower, Mel was on the deck sipping coffee.

"Are you sure you're okay with it Mel?" I asked, saying I could only get a single spot golfing at Torrey Pines.

"It's a bucket list thing, I get it...You go in the morning and I'll shop," she said, rubbing my arm while we were heading out for lunch. "We have all today together."

I messaged Richard I had spots and to meet me in the parking lot at 8 a.m.. Lunch, the beach, seeing the sea lions and doing dinner made up our day. Instead of going to a club we retired to the hot tub and enjoyed the fresh air outside on the patio the rest of the night. We kissed, did some light petting but were tired and sometimes sleep is better than sex and in my situation I didn't press.

Getting up the next morning, I did go for a run early at 5:30 a.m. and took off for the golf course at 7 a.m., Mel was just getting up and got a quick kiss goodbye. I was pretty proud of my plan, using the course that had hosted two U.S. Open's as a way to get extended time with Richard. He was going to have to be in a polo and nice shorts, but I instructed him to wear black panties.

To my delight he pulled in just 10 minutes behind me, I was 20 minutes early, he hopped out of his car and we embraced quickly.