Sailing Away Ch 19

Chapter 19 - truth or dare

So after I licked your ass sufficiently to please you... we both drifted off to sleep. Brian was due back on shift, so hopefully he got at least a couple of hours of sleep after fucking you and Elsa silly.

When I awoke, the low LED light was on, and you were digging in your suitcase for something.

"What are you looking for?" I asked.

"Oh, something to tie you down to the bed." You return with a pair of stockings. "These will do nicely."

You secure each of my wrists to the frame of the bed, so I'm spread apart for your pleasure. I'm still dressed, shorts, shirt, underwear. But that doesn't matter; leaving my shirt in place you undo my belt and pull off my shorts. I'm as helpful as I can be given conditions.

Leaving my panties in place, you mouth my cock cage through them, and kiss my thighs.

"So now that you've heard some of my secrets, I want to hear some of yours."

"Yes ma'am, what would you like to know?"

"We'll start with which came first - wearing women's undies, using nail polish, cuckolding or the cock cage?"

A lick on my balls through my panties is a welcome distraction.

"I started wearing girl's panties when I was a teenager."

"Now, how was it you began wearing women's underwear? Steal them from your mom? Your sister? A neighbor? Get turned on looking at Victoria's Secret catalogs or something? Maybe their NFL halftime show?" Continued kisses on my thighs, my own undies getting pulled to the side...on, but everything exposed.

"More like a girlfriend wanted me to swap underwear with her."

"She wanted to wear yours," a lick to my balls, "and she wanted you to wear hers?"

"Yes ma'am, exactly."

"That's interesting. I take it you did?" Mouth on my cage, and a lick through one of its holes.

"I was game. We both liked it. So now and then we'd both wear each other's. She stayed at my place a fair amount, so she kept some stuff there. Eventually we'd just pick from each other's underwear and wear them. When it came to laundry, nobody noticed the difference."

You took hold of my cage and stroked it, giving me a little sensation but not much. Still, even though I couldn't cum, it felt good.

"She like to have sex with you in your undies?" The stroking continued.

"Yes ma'am. She also introduced me to dildos and vibrators. Didn't have a strapon at the time but she'd simulate it...she'd hold on to her dildo and fuck me with it like it was her own cock. Was incredible."

"Did she make you cum from fucking you in the ass?" Stroking while licking my balls again. It's like the perfect blowjob...almost.

"No, that didn't happen until quite recently. But she'd stroke me some while fucking me, and that did it. Even if she wasn't simulating a strapon, she'd fuck me with her dildo and suck me off, which worked every single time. Wow, what memories."

"She ever bring a guy around to fuck you?"

"No ma'am, neither of us had any interest in other partners. That was a lot later."

We stop for a moment and listen...sounds like Elsa and Brian were back at it.

"So you weren't her cuckold? Shame." More licking, and the stroking never stopped, keeping me wonderfully hard, but going nowhere.

"No, that wasn't until a few years back. With another girlfriend."

"So if girls panties were first, what came next if it wasn't cuckolding?" You sat up between my legs, stroking, massaging, and looking at me.

"Actually it wasn't any of the above, it was more women's clothing. I already had started a collection of panties, it just seemed like a natural progression. But it wasn't until many years later, when I was about 30." The memories were arousing, and I rocked my hips and readjusted in the sheets, my arms no help at all.

"How did you do that?"

"Started with shoes. I just ordered online. Found some heels I liked, got them sent, bought more. Never thought I'd have trouble with heels, and wore four and five inch heels without much issue at all. Ended up with plenty, like twenty pairs or so."

Continued stroking and massaging. Varying enough to avoid persistent stimulation, feeling wonderfully teasing simultaneously.

"What did your girlfriend think?"

"This was while I was still married. She was fine, she was kinky too, so wasn't an issue. My girlfriend was also supportive, even more so."

"How was she more supportive?"

"Because she wanted me to wear heels and undies to fuck her. Which resulted in me eventually buying stockings to go with the heels. And you can't have stockings without garters sooooo... The collection expanded."

"Ooooooh, so she liked this?" Moving a hand, you lifted one of your tits to lick your nipple, knowing how much I loved to see it.

"Yes ma'am she did. To the point she'd pick out what she wanted to see me in. Loved to have me stand and she'd suck my cock while sitting on the couch. Of course, the combination ended up evolving into her fucking me with a strapon too...which I absolutely loved. The combination was incredible."

You kiss your nipples alternately, then return to my cage, masturbating me with no chance to cum. "So we have girls panties, toys, shoes, then stockings. What's next? Nail polish? Cage? Something else naughty?"

"Next came nail polish. That was again a simple evolution or extension of what came prior. I figured, why should girls have the good looking toes?"

"So how did you start? Just go out for a pedicure and pick out some hot pink polish?"

"No ma'am. Public pedicures didn't happen for a while. I did my own initially, had a few colors, and slowly got better at it. Over time I built up quite a collection of polish. Metallics, color shifting polish, cream colors, matte colors, all sorts of stuff. For a while I was dating a girl who loved to trade pedicures with me. Was very connecting. We'd see each other every couple of weeks, and typically spend part of an evening doing them for each other. She gave me a really long massage and detailed pedicure for my birthday one year, quite memorable."

You move out from between my legs, and lay next to me, head in your hand, and the other blithely wandering my chest. Stopping to pull up my shirt, you continue on my chest, but end up focusing on my nipples, massaging, pressure-pinching. Heavenly.

"Sweetie, how did you get to doing them in public?"

"I had a friend who knew I loved having my toes done. So she eventually convinced me to go with her. I was hooked immediately. We'd pick out colors from my collection, and go to the salon every 3-4 weeks together, with lunch before or after. Eventually the girls at the salon would ask where I was if she went alone. MMMMmmmmm oh, Mistress, that feels so good." Your tongue flicking my nipple resulted in my last sentence.

You smile around your extended, busy tongue, the hand that was on my chest back to my cock.

"Any particularly memorable salon visits?" Back to my nipple, slow sucking. I was distracted until you nipped it hard, reminding me to continue.

"Once I had a manicure at that salon...with color."

"Tell me about that, I wanna hear all about it!"

"We'd done manicures before, her far more often than me. She had some financial difficulties following her divorce, so I'd treat her for the salon, which was as much a treat for me since I got to go with her. So she usually got fake nails done, which looked fabulous on her, and I was happy to pay for them. I sometimes fantasized how they'd look wrapped around my cock. Once we had a particularly good looking purple for our toes, and she teased me into doing my fingers. So I did. And I LOVED it, just couldn't wear it long because of work."

"Baby that's hot. How'd you get home from the salon?"

"I lived about 40 minutes from her, so we drove from the salon to her house, and I dropped her off, then I drove home. The windows in my car are tinted, but I kept my hands on the wheel, not in my lap."

"MMMmmmmm...my exhibitionist boy."

"Yes ma'am, at times. There are a few others."

"Tell me about a memorable one."

"Once I decided to show up to see my girlfriend dressed in girls clothes head to toe."

"Oh, this I gotta hear!" A smile and a kiss on my cheek.

"At that point I worked about an hour from home. So I planned everything, and put all the necessary stuff in my truck. On the way home, I stopped at a deserted interchange on the freeway, hopped in back, and switched out of my work clothes into my other clothes. It was dark, so nobody would notice. Black lace thong, sleeveless high neck minidress, garter, fishnets, 4" black heels, a lot like the ones we brought on this trip. So I get to her house, only to find out that I can't park in front because that spot is already occupied, I have to park on the corner. And the front light is on, when it was usually off. I figured I had already planned to walk fifty feet to the front door, might as well walk the hundred or so from the new parking spot. Put on my heels, looked around to make sure no neighbors were out, then strolled up to the door and knocked. As soon as she opened it she smiled and kissed me. I could have been out of those clothes in a few minutes, but neither of us wanted that!"

"I love that story. Makes me glad I had you run around San Francisco with nails and makeup done." A kiss, followed by another question. "So what came next? The cage?"

"Yes ma'am. Like many guys, I got interested and perused a bunch on tumblr. Eventually got the guts up to order one. I went cheap with a silicone one at first, not knowing what to buy. It was okay. One night when she was over I excused myself, put it on, and came out to give her the key. She asked what it was about, and I pulled down my sweats and showed her the blue cage on my cock. She loved it instantly! Thus started a period of tease and denial. I didn't wear it for too long back then, not like how you have me locked up. But a couple of days here and there. Eventually invested in a couple to try, and settled on something like what you keep me in."

"How'd it go from there?"

"It was a lot of fun. The girl I showed it to first, Melissa, was essentially my first keyholder. But she and my other girlfriend Nina conspired, and teamed up. So they'd coordinate how long I'd stay locked, who was going to unlock me when. They loved it. So did I for that matter."

"What's the longest they kept you locked?" Another kiss, and you straddle my abdomen, dipping your tits to just out of reach of my tongue...the key vivid in my vision.

"Probably 2-3 days at a time. Nothing like the ten days you kept me locked that one time."

"Yes, that was dreamy for me. So many orgasms on your tongue. So much cum from your cock when I ruined you afterwards and had you lick it up. MMMmmmm, that was wonderful."

"Yes ma'am, it surely was."

With that you dipped a nipple to my mouth, and I eagerly lapped it up, sucking, twiddling it with my tongue, nibbling softly. You pulled it away only to replace it with the other, dragging the key across my face in the process.

"A little harder, sweetie, I want to cum from my nipples."

I enhanced my effort, and nibbled harder, pinching with my teeth, almost a light chewing motion. You reached up and pinched the free nipple, then backed away, put both tits together so nipples fit in my mouth and leaned back down. Promptly chewing your nipples in tandem, you tensed and moaned out an orgasm.

Stroking my head, "Mmmm that's a good boy. So we've got panties, shoes, stockings, polish, and the cage. Where did the makeup come in?"

"Melissa liked me dressing up enough she also encouraged me to do some makeup. She didn't push it, but mentioned it a couple of times, so I bought some and gave it a shot. Eventually I got a little of everything - foundation, blush, eyeliner, mascara, eye shadow, lip liner, lip gloss. I didn't develop near the variety I did with shoes and panties, but I had a little bit. And I particularly like what you brought for me on this trip, and what I got at the MAC store yesterday."

"You like wearing it out from the store, hm? For all to see your cuteness all dolled up?"

"I was nervous mistress. But I'd done some before. I'd gone out with purple nail polish that one time, although not for that long. And I'd been out with subtle lip gloss and eye liner before too. Not enough to be obvious, but I knew it was there."

"See, I knew it wasn't your first time." A nipple in front of my lips, just a bit out of reach. "Make me cum again and I'll untie you."

I returned to the nipple in front of me, and protruded my tongue as far as I could. You teased, but eventually let me lick, suck and nibble you to orgasm. My mouth still on your tit, you reached up and untied me, then withdrew and took off my shirt, laying down next to me. I reach out to turn off the night light. As I reach for the light, I see the bedside clock. It's 545am. Unless Brian got Alan to cover part of his bridge shift, it couldn't be him. Maybe she's been playing with her dildo.

Both of us nodding off, we hear the door squeak slightly, and the hall light intrudes, casting Elsa in shadow. She quickly closes the door behind her, crawls in behind me. I can feel her drenched pussy on my leg, her juices mingling with Brian's, now on me. She's sweaty and I can smell sex all over her...is there more? Centered between you, you both kiss each other across my chest, then lay your heads on me. In the pitch black, the two of you sleep quickly, orgasms encouraging your slumber.

My locked cock and I stay awake for quite a while, your hands interlocked and resting on my cage. There's so much cum leaking from her twat there's no way it's just Brian's. It's quite some time before my erection subsides enough for me to sleep.