Boat Talk

Just a fun story of two old friends catching up. Be warned, the little three asterisk thing; ***, indicates a change in voice. Dave is our main storyteller, but Rick gets to tell his story, too, so just be aware.

All standard caveats apply, over 18, happy ending, etc. I hope you like my story, and please leave me a comment when you're finished reading.

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This was not where I expected to be, sitting on the back of a hundred-foot yacht somewhere in the Caribbean with Rick.

Rick and I had been tight in high school. He was a pitcher, and I played shortstop. We won some state championships and were sort of local heroes. I was good enough to get a scholarship and earn a couple of trips to the College World Series; we even won it once. But Rick; The Rangers drafted him out of high school. He earned three World Series rings and a Cy Young award before a freak accident ruined his career. He had turned his multi-million-dollar salaries into a massive investment portfolio worth a hundred times what he had started with.

I had gotten a PhD and taken a job teaching at a small Division 2 school, teaching English and helping with the baseball team. He lived a life that involved, well, sitting on the back of his hundred-foot yacht drinking mojitos and pina coladas and stuff like that. That, and managing his investments.

Why he came back for our ten-year high school reunion was beyond me, but there he was, and it was like we had never been apart. We drank beer and told war stories, swapping blatant lies about what we had been doing. We called each other out and then fabricated something more outlandish. It was just like old times.

"So, where's Meg? Is she not up to sitting around while you rehash your meager high school accomplishments?"

Rick had been a groomsman at our wedding, and it was a valid question.

"That's a conversation for another day." I gave a nervous chuckle and finished my beer. "We, uh, we're not together anymore. What about Mary?"

Rick looked like he was forming words, getting ready to answer, when he stopped, cocked his head and looked right at me with the strangest look on his face. I knew that look all too well. Some outlandish proposal that was going to get both of us kicked off the team usually followed it.

"What are you doing this summer?"

"Not much. I'm taking a mini sabbatical and not teaching summer school. Recharge the batteries. That sort of thing. Why?"

"I miss this. You and me like this, like it used to be, and, well, Mary and I split up, too. I was just thinking we had a lot more to talk about than just lies about baseball. Why don't you come with me? We can go hang on my boat and really talk about what we've been doing. What went wrong, what went right. Kind of like going out to the old mill with a sixpack we stole from my dad when Sara Beth dumped you for that college guy, except on a boat."

"I think I'd like that. Why the hell not?"

A week later, there we were, moored just off some island I'd never heard of, sitting in the sun, drinking foo-foo drinks with too much rum in them.

We had exhausted all the potential distractions, so when he said, "And you and Meg, what happened there?" I knew I had no escape.

"Why do I have to go first all the time?" I half hedged. I knew the answer to that one, too.

"Because your life is always more dramatic than mine and your stories are a lot more interesting." We both just laughed. As much as I hated to admit it, I was a drama queen, or king, well, maybe queen...

"You want the whole thing, all the nitty gritty, don't you?"

"You know I do. Besides, it's therapeutic. Don't you always feel better after you bare your soul to 'Rick the Confessor?' And I'm pretty sure my story is worse."

"Yeah, don't bet on that." I laughed.

***

"God, Meg, you are so damned sexy." She and I had just gotten home from a charity event, and she was getting undressed. The lingerie she was wearing told me she had intimate plans for the two of us now that we were home. Her coy smile and the way she bit her lip as she turned to face me wearing her bright pink matching bra and panties, with a garter belt and stockings, still in her heels.

"You like?"

"You know I do. Now come here and let me get a closer look." I smiled back at her as I tossed my jacket on the chair by the bed, kicked off my shoes, and slowly unfastened my tie. Damn. She slunk across the bedroom like a cat on the hunt.

"Let me." She slid her hands up my chest, pressing her body against mine as she gave me a quick kiss and pushed my hands away from my tie. Holy fuck, she bit my lip and buried her tongue in my mouth.

Of course, I had to find something else to do with my hands. I explored the soft landscape of her body, relishing the mixture of her soft skin and the satin and lace that barely covered it.

Up over my shoulders and down my arms, my shirt found the floor as her hands slid back down my chest and unfastened my pants, letting them drop to my ankles. My boxer briefs quickly followed, and with a gentle nudge, I fell back onto the bed. Meg shimmied out of her panties and climbed on top of me, taking my leaking erection into her core. She arched her back, and unclasping her bra, released her immaculate breasts.

She had this thing she did when she rode me like this, hooking her feet over my thighs so her stockings teased my skin as she writhed above me. It drove me insane, and she knew it. I loved the feeling of her stockings on my skin almost as much as I loved the way she looked wearing them.

Meg chased her climax while she drove me crazy. My hands explored her body, massaging her pert, firm breasts and tweaking her nipples. They slid down her taught body to her hips, and then to her thighs, where I ran my fingers over the nylon that covered them. She knew me so well, me and my stocking fetish.

"I want you on top." Meg leaned down and kissed me, running her hands down my arms, entwining her fingers with mine, and pulling me over as she fell onto her back. Without letting go, I dove back into her pleasure, thrusting hard and fast just like I knew she liked it. Furiously, I fucked her as her legs roamed over my thighs, butt and lower back, caressing me with that magical nylon. When she came, it shook the entire bed. When I followed her a few minutes later, the spasms running through my body made me go limp. I collapsed on top of her. She just laughed.

"You love it, don't you? The feeling of my nylons on your skin."

"You know I do. The only thing sexier is seeing you in them."

"You should feel what it's like to pull them on over freshly shaven legs." She let out a soft moan and ran her right foot from my ankle to my thigh. All I could do was shudder.

"You could, you know."

"What?" I was still half dazed from the sensory overload.

"Shave your legs and try on some of my stockings. I'd even hep you shave."

I laughed and rolled off my beautiful wife, propping myself up on my elbow.

She looked up at me with that special look in her eyes that told me she wanted something she knew I was going to give her. Then she bit her lower lip...

"You're serious?" I asked incredulously. She nodded.

"Dave, admit it, you have a stocking fetish." She laughed. "You'd get off on it and I think it would be sexy as hell. Besides, I want to feel what you feel. I want you to rub your stocking all over y naked body like this." She rolled toward me, running her nylon covered calf up and down my leg and thigh.

She was right. She knew it. I knew it, and if she'd asked, I'd have been honest and told her I had wondered, well, maybe fantasized is a better word, about that very thing a time or two.

"You really want to see me in stockings?"

"Garter belt, too. I don't have any stay-ups." That look in her eyes changed ever so slightly. Now she looked hungry.

I hemmed and hawed, trying to come up with reasons it was a bad idea. Looking for anything to defend my masculinity, and to not let her know, I really didn't need convincing. It ended just as we both knew it would: the two of us in the shower and Meg teaching me how to shave my legs.

"There." I smiled at her as I ran my hands over my legs. "How did I do?"

"Nice." Her hands replaced mine and then everything changed. Meg took the razor from the small shelf and kept going. "Just relax. You'll love it, I promise." My cock and balls, then my stomach and chest. "Lift your arms." I did what she asked. The water was getting cool, and I was hairless from my nose down. She even had me bend over and shaved my ass.

"Pat, don't rub." She handed me a fluffy towel. I did as she asked. When I was dry, she started slathering lotion all over my body. It smelled like her, which I found so damned erotic. She was rubbing it into places that, while familiar to her touch, were now completely hairless and sensitive as hell.

I was rock hard, and she was on her knees in front of me. My eyes were begging her to take me in her mouth. Grabbed my soldier; she gave it a gently tug, and stood up, using it to lead me out into the bedroom. Patting the bed, telling me where to sit, she disappeared into her closet where her lingerie chest was. She came out with her hands full of satin and lace and a smile that would have made the Cheshire Cat jealous.

My god, she was right. The garter belt was one thing, the way the lace tickled and teased my waist and hips, and the straps tickled my thighs. But when I pulled the stockings up my legs, fuck, I almost came, and neither of us had touched my cock since she led me out here with it.

"Stand up." I did. "Turn around." Once more, I did what I was told. "Don't move."

"Meg, what are you doing?"

"Just wait a minute." Her voice sounded like she had gone back into her closet.

"Lift." She patted my left foot. I felt her slip something around my ankle and then slip my toes into a pair of shoes, her shoes, and from the way they pinched my toes, they were heels.

"Meg?" I protested.

"Just trust me." She patted my right foot, and I grabbed the bedpost and did my best to stand on one foot in what felt like the highest pair of heels she had.

"There." I felt her slip the other shoe on and I put my foot down before I fell over while something slid up my legs. The same wonderful feeling I had experienced with the stockings sent shivers up my spine and something so delicate, so soft, encased my balls. Fuck, she was putting me in panties. She snugged them to my body, and I trembled when they gave me a slight wedgie, but I could feel the lace trim tickling my ass as the garter belt did my hips.

"I thought you said just stockings." It was more of a moan than anything else.

"Are you complaining?" She ran her hand over my ass and patted me on the butt.

"I might if I could think straight." I laughed. "How do you do anything dressed like this?"

"Don't move." She laughed, leaning over my shoulder and kissing my cheek before disappearing one more time into her closet. She was torturing me. Maybe not intentionally, but the effect was the same.

I tried not to move, I really did, but I couldn't help but take a few small steps in the heels, just to feel my nylon covered legs rub against each other. I had to touch myself, too. Running my hands over my hips and butt. My god, I was dying. It felt so electric. I rubbed my legs together some more and giggled as my body trembled.

"Arch your back and look over your shoulder, baby." Meg slid up behind me, running one of her legs against mine. Shit, she had changed, too.

I did what she said and couldn't believe what I saw in the mirror over our dresser. From the waist down, there were two perfect asses sitting atop nylon clad legs, in matching black heels. I knew my garter and panties were pink, so the red was Meg's. Damn, I had almost as nice an ass as my wife did, and my legs were longer and more muscular. Fuck, I'd fuck me. I laughed at the thought.

"Nice, isn't it? Now come to bed with me and let's see what kind of trouble we can get into." Meg put her hands on my cheeks and pulled my lips to hers. We tumbled onto the bed as our tongues fought for dominance and our hands exploring with wanton abandon, our nylon covered legs writhing together like mating snakes.

Meg rolled onto her back, ripping her thong off and spreading her legs. I didn't need any more encouragement than that. Diving into her wetness, I came faster than I had since I was in high school. Meg continued to rub her legs against mine, using her feet to massage my calves while her thighs and mine caressed each other. Even the lace on our garter belts felt good, and the band of my panties nestled just under my balls was doing things to me I couldn't describe.

Aa I laid there on top of her, still inside her; my cock got hard again. I kissed and licking her tits while her chest heaved underneath me.

The beast in me roared. I fucked her more ways than I could count. Missionary doggie style, sideways. She sucked my cock and rode me cowgirl style, before finally laying on her back and begging me to fill her up the third time.

When I was done, I collapsed next to her. I felt like I had run a marathon. Meg and I were both panting heavily. She slipped one leg over mine, rubbing the nylon of her stoking against mine.

"We are so doing this again." She laughed.

I didn't say a word. I just smiled and shook my head. It didn't matter which way because Meg was right.

***

"Fuck man, Now I need to go jerk off." Rick laughed and got up to get us another drink. "I thought you were telling me why Meg and you broke up. That was hot as fuck. How did you let that go?"

"I'm not drunk enough for that part of the story yet." I laughed and grabbed the drink he offered me.

"So, meg dressed you up in lingerie and fucked your brains out and that was a bad thing?"

"Nope, but it was the beginning of the end." I practically drained my entire drink in one pull.

***

Meg and I fell asleep in each other's arms covered in sex, sweat, and, of course, nylon, satin and lace. I woke up to my cock buried in her throat; her legs crossed across my chest and one of her hands caressing the nylon on my leg. I ran my hands up and down her thighs until I exploded into her eager mouth. The feeling of her stockings sliding across my body as she switched positions was electric. She brought her lips to mine and kissed me hard. What I didn't expect was the impromptu snowball we shared.

I may not have known where the kinky ideas were coming from, but I wasn't going to complain.

She laid her head on my shoulder, nestling under my arm, and tucked my flagging erection back into my panties.

"I like you like this." She kissed my cheek sweetly. "I was serious when I said I wanted to do it again. Are you ok with that?"

"It does fell pretty amazing." I drew my leg up, sliding my calf along hers. "And I guess I do have a bit of a nylon fetish."

We showered together and went out for brunch. On the way home, she directed me to a little out of the way shop that specialized in lingerie. Hers had worked, but I agreed I should probably have my own if we were going to continue exploring my fetish like this. We were shopping for stuff specifically for me.

I ended up with more stockings than I thought one person could ever wear. There were a dozen garter belts and twice as many pairs of panties. All satin and lace, and all thongs or what they called cheekies (panties that crawled up the crack of my butt and ticked my cheeks with their lace trim). Some of those came in sets, which gave me half a dozen bras, too. The thing about this shop was it specialized in what they called cross dressers, so everything fit my body perfectly. I balked when the salesclerk offered forms to fill out the bras if I wanted larger cup sizes.

When we got home, Meg gave me a crash course on how to take care of satin and lace, and then we got dressed in matching lingerie, and fucked like rabbits until we passed out. It was incredible, but it was going to kill me.

And that's how it went for a while. I'd come home on a Friday and meg would have laid out some lingerie she wanted me to wear. I get cleaned up and dressed and then go find her. Wherever she was, we'd fuck and rub against each other, chasing one orgasm with the next. She was insatiable. I was just doing my best to keep up and loving every minute.

I don't really remember exactly when it happened, or why. But Meg went out of town for a weekend, and I missed the sex. I missed the feeling of the lingerie. I missed it all. So, while she was gone, I picked out the sexiest set I had and took my time putting it all on. One of her bath bombs roiled the water as I shaved closer than I ever had before. I used her most floral-scented lotion. All of it. Hell, when I realized the panties I chose had a matching bra, I even put that on.

I must have stood in front of the damned mirror for an hour just admiring myself, rubbing my hands all over my body. Not just the parts covered in soft, frilly fabric, but all the places Meg touched when we made love.

I always thought stockings were my thing. The truth was, I loved all of it. When I massaged the lace from the bra into my breasts and my nipples got hard, I knew it was more than just that. It wasn't just about the sex. When I looked at myself in the mirror, I did it the same way I looked at Meg. I wanted more, needed more.

I went into Meg's closet and put on a pair of her heels and stuffed stockings in my bra. It was like something deep inside me was waking up. All weekend, I played dress-up. The interesting thing was, I never jerked off. It wasn't sexual. It was different, almost visceral. I even stole some old clothes from the back of Meg's closet. Things she didn't wear anymore and wore those around the house. The sexier, the more feminine, the better.

Sunday afternoon, when Meg came home, it was game on. I had three days of pent-up desire saved up and it was amazing. Monday morning, though, I went to work wearing a pair of panties and a bra; I just didn't tell Meg.

I started looking for opportunities to get dressed up. My stash, the clothes I had stolen from her, was hidden out in the garage in a plastic tote I put up on the roof rack. Don't ask me why I didn't just put it all back where I found it. I don't know. Maybe I thought she'd clean out her closet and give it all to The Salvation Army, or something.

I started spending my office hours surfing the web, looking for information about men in dresses. There were websites that supported it, and some that defiled it as sick and perverse. I needed to know more. There were pictures; tons of them. Most of them looked like you would expect. Some, though, some were stunning, and some of those posted links to tutorials.

Meg would go out with her girlfriends, and I would say I had grading to do, when, in fact, I was practicing putting on makeup and taking it off so I could do it again.

It was subtle and slow, Meg going out with friends more often, and me letting her, pretending I had other things to do. I didn't know what she was doing or who she was with, but I knew while she was gone, I was going to be dressed as a woman with my makeup perfect, probably online in a chatroom. Most of the time, it was with other cross dressers. Occasionally, though, I would be in private pay sites, sending strangers pictures I had taken with a small camera I kept hidden with my stash.

Most were decent, but a few, a growing few, were sexy. For one friend, they had gotten risqué, with me in my lingerie doing seductive poses. I had even gone back to that boutique Meg took me too and bought more. Corsets, skimpier panties and bras that would support my C cup forms. All for me and my online friends and none that Meg knew anything about.

I could feel it and I knew Meg could too. We were drifting apart and while it should have been obvious to me; it wasn't. Meg was clueless.