Cruising for a Bruisin' Ch. 01

"Well, as long as you're not going to ask me to marry you..." I slid out from the table and offered Eric my hand. As we went past his table, his buddy handed him a $20 bill. I laughed and said over the music, "I'm only worth $20?"

Eric leaned down and said, "That was the price to ask you to dance. You don't know what he agreed to pay me if I could get you to go home with me."

I laughed again then put my arms around him as a lovely slow song started up. We held each other close and I felt a very large something pushing against me toward the end of the song. I knew I shouldn't do it, but I pushed back against it when it brushed up against me the second time.

"Sorry," he said with a smile. "It's just hard to keep that from happening with someone as pretty as you."

I smiled and said, "Well, it most definitely IS hard."

As the song ended, he said, "Do you mind if I kiss you?"

"If you cut me in for half of your next payment then...okay," I teased.

He leaned down and kissed me full on the lips. I kissed him back and said, "I'm afraid that's all the money you'll be winning from your friend tonight."

As he walked me back to the table, he grabbed another twenty from his buddy and said, "If you change your mind, I'll be right there the rest of the night."

I smiled, thanked him for the dance and the kiss and sat back down. I slid close to Tim who put his arm around me and said, "Okay. That was very hot. If I thought he wouldn't beat the shit out of both of us, I'd suggest we..."

I pulled myself right next to him and said, "Hmmm. I was thinking the very same thing. But he doesn't look like the kind of guy who'd be understanding of that um...special something you like so much about me."

Tim groaned and said, "You ready to go home?"

"My place or yours?" I asked coyly.

"Since I drove, it might be best to go back to your place," he suggested.

I didn't like getting up in the morning and driving home with beard stubble showing so I agreed. (I've had a modest amount of electrolysis so my facial hair is sparse and very light, but it doesn't take much to give a girl like me away, so I was happy to have Tim stay at my place.) Of course, that meant I wouldn't be getting much sleep but it was the weekend so...

Tim kept a toothbrush, razor, and shaving cream at my place but that was it. No matter how much I like a guy, he's just not ever moving in with me. So while he was in the bathroom brushing his teeth, I got ready for him.

I'd already given myself a very thorough enema before dinner so everything was clean as a whistle...in there. I slipped off my suede skirt and knit top, then carefully pulled off my padded undergarment being very careful not to break a nail. I lightly glue them on so they won't just fall off in public, but it isn't hard to snap one off!

I was standing there in my bra and panties, stockings, garter belt, and heels but as you might guess, I don't feel complete without a sweater of some sort. I was wearing a lacy white bra so I chose a rib-knit, white cardigan to wear to bed. I love, love, love seeing the rib knitting around my tiny wrist while I'm holding my lover's cock. Yes, I love seeing my red nails (or kind of a copper color this night) but for whatever reason, the ribbing just does it for me.

We men hold nearly 100% of the paraphilia/fetishes and I don't even bother trying to understand why anymore. I/we like what I/we like. End of story. And since Tim didn't care, why wouldn't I wear what makes me feel pretty and feminine? (That's rhetorical, of course!)

Just one thing left to do. If you've read my other adventures you know I don't like having any man touch my cock. I made an exception for his best friend, Dave, because Beth, who is SO smoking hot, basically begged me to let him suck my dick. I think she wanted to tease him about it later on. Then again, maybe he's got a true cuckold fantasy of being humiliated. Who knows? I just let him do it because well, Beth is so fucking gorgeous and I really got caught up in the moment.

The panties needed to go so I slipped them off then pulled on a pair of pussy panties which give the rough illusion of having a vagina. They have an, um...access port...in the back in a strategically-located position so on they went. I lay down on the bed on my side propped up on my elbow with my legs slightly spread apart waiting for my handsome boyfriend to come fuck me good night.

When he came out of the bathroom, he was already sporting wood. "You taking Viagra?" I teased.

"No. I definitely don't need that," said with a wicked smile. "It's just that waiting an entire week to make love to you is an eternity. Do you have any idea how horny I get going 5-6 days without having sex?"

I raised my eyebrows and said, "Um...yes, I believe I do." My own phallus was growing but the material in my faux pussy was doing a good job of concealing it. "In fact, I'm so horny I can't stand it. Can you bring your gorgeous body and beautiful cock over here and let me take it in my mouth?"

Tim slid onto the bed and lay down next to me. I raised up and started kissing him as I ran my hand down his hard body to his even harder cock. "Mmmm. That feels so good, honey," I whispered. "I love your pretty cock."

Tim moaned. "God, that feels good, baby. I love the way you make me feel," he said to me.

I ran my hand down under his scrotum and ran my thumb between his right ball and his leg. When Tim groaned, I knew he enjoyed it as much as I always had. "Feel good?" I said.

"That's amazing!" he replied. "Keep doing that."

As I continued doing what he wanted, I made my way from his soft lips to his chest to his tummy to what I wanted most of all. "Mmmm. I've been wanting you so bad all night, honey," I said as I lowered my warm mouth onto his throbbing cock. I sucked on the head using my tongue on the underside. Tim groaned even louder as my thumb also kept doing its thing.

I took him deeper and deeper until I couldn't open my throat any wider. I held it there until I felt a gag reflex then bobbed up gasping for breath leaving long, thick streams of saliva. "My God, that's beautiful!" Tim gasped.

I alternated between sucking and deep throating for another couple of minutes as my thumb and fingernails continued to work their magic. I knew Tim was getting close when he pushed my shoulder back. "You ready to fuck me?" I asked playfully.

"Get on your fucking knees, bitch," he ordered me.

"Mmmm. Someone wants to be dominant tonight. I like that," I said with a smile.

I got on all fours as I was told and felt warm lube being poured into the crack of my ass. I felt Tim's hand rub it into my ass as one of his fingers prepped my hole. I gasped. "That feels so nice," I whimpered. "I want more."

"Oh, you're gonna get more tonight, bitch," he promised.

I felt Tim start pushing against me just as he slapped my right butt check. "Yes!" I said. "More, please!"

Tim slapped my ass until it was glowing red even as he gently but firmly pushed the head of his sweet cock into my bum. I absolutely adored the way it felt when it popped inside of me. I moaned and begged him to fuck me hard. Moments later, I felt his massive cock hit my prostate gland. "Fuck yeah!" I moaned. "Just like that, honey," I begged.

Tim obliged me as he hit the right spot over and over and over while slapping my small ass. I felt like I might cum myself as I felt Tim tense. Since he'd been clean on three tests in a row, I had decided to let him cum inside me. I loved the feeling of hot cum splashing inside my body as my lover shot his full load into me.

"Oh, my God!" I cried. I felt myself losing control and in spite of the way my cock was being held down, I felt long streams of sticky goo flow out of me as Tim came inside me.

Even after he pulled out, I was unable to move. Both of us were panting and I was basking in the feeling of having been freshly fucked by the man I loved. I was dressed as a woman wearing a beautiful, lacy bra, a pretty sweater, stocking, heels, and jewelry. I was so happy, I felt like I might cry. I couldn't help but wonder what it would be like were I to start taking female hormones...

"You're leaking, sweetheart," Tim told me. He was resting on the pillows as his cum dripped out of my hot ass. "And your ass is beet red. You should get that checked out."

"No need. My boyfriend beats me," I said matter of factly. I paused then added, "And I love it."

I finally turned around then crawled up on top of him. I put his arms around me and said, "Do you know I love you, Callie?"

"Yes," I answered. "And I love you, too."

"Enough to let me fuck you again?" he asked as though it was unlikely.

"Just once more?" I said wantonly.

"Let's see," he said as he rolled me over and mounted me from on top. His hard cock slid right back inside me as I raised my legs as high and wide as I possibly could. "Feel good?" he asked as he began pounding me again. All I could do is nod and whimper until he came inside me a second time. He woke me up at 2am for round three and fucked me goodbye in the morning. I was so (blissfully) sore, I couldn't even go running until late in the afternoon. Even then, I had to be careful as I was prone to releasing some of the most awful-sounding flatulence imaginable. But it was oh-so worth it!

Over the next three weeks, I did as much research as I could about what to bring on our cruise. I wanted to be able to dress up but I also knew I'd have to fit in. I didn't care for jeans or any kind of pants, but there was no way I was going to able to wear skirts and heels for five days straight. So... I found some excellent blog links where women shared their packing lists. It confirmed what I already knew. A warm coat, gloves, lots of sweaters (yum!), jeans, comfortable shoes (big downer), but also some nice clothes for dinners and dancing onboard ship.

I managed to pack everything into two suitcases, a makeup case, and my purse. I had another full body wax before going and for the trip. For the flight to Seattle, I chose a very soft, pretty, blue cashmere sweater, a black skirt that fell to about three inches above my knee, and a pair of 2 1/2" black heels. I wore silver earrings, a silver necklace and a matching watch along with my faux wedding ring. (I have two of them, by the way. One is gold and the other silver. Hey, a girl can't have too much jewelry, right?)

As I mentioned, I'd had to coordinate with the airlines and TSA in advance to let them know I was biologically male but flying as a woman. I'd read about some horror stories, but I was willing to suffer fools in order to be myself. As it turned out, it was much ado about nothing. In fact, one kind lady even advised me not wear an underwire bra to avoid being singled out for further scrutiny. Everyone was very courteous and no one called me "sir" when I quietly told them who I was on the passenger list or said anything that made me feel uncomfortable in any way. That was especially nice because we had several children and teens on the flight and none of them looked, snickered, or giggled. Then again, I didn't expect anyone would unless a TSA agent went rogue and said something along the lines of, "Hey, everybody, this is a dude!"

We sat in business class and about half way through the flight the first officer came back and asked several of us how we were doing. We were in row 4C and when he got to us he said, "Let me guess. You two are on your honeymoon, right?"

Tim smiled and said, "How'd you know? Is it that obvious?"

The co-pilot looked down and said, "You're holding hands. Who else does that?" He winked, smiled, then moved on to the next row behind us.

I hadn't been back to Seattle since I finished my MS in engineering and left for Virginia. It really is a beautiful city, especially on those rare days when the sun is shining. We got there about noon and it was one of those days where the sky is so blue that the white of Mount Rainier in the background is breathtaking. Tim had never been there so after we got settled in our hotel room, I agreed to show him around.

I took him to Pike's Place Market, which is a must-see for any first-time visitor. There's shop after shop of fresh seafood and all kinds of other things to buy. We also had enough time to take a taxi to the Space Needle and take the elevator to the top. We walked around the perimeter enjoying the sunny, 65-degree temp that made it possible for me to go out in public without melting. In fact, it was very pleasant.

Tim took me to dinner in the hotel restaurant then fucked my brains out later at the hotel. This was the first time I'd ever stayed with a man more than overnight so I warned him about my need to prepare each morning and evening. He didn't mind at all but I just have this thing about being seen as the real me by someone I'm dating. I made him stay downstairs as I shaved, showered, and did my makeup. Once I was ready, I sent him a text and told him he had permission to come home!

It was going to be a balmy 50 in Anchorage so I chose a very pretty, heather-gray turtleneck sweater to wear with a pair of modestly tight jeans on the flight to Alaska. I like the way tight jeans look, but they are very uncomfortable to wear for long periods of time. I decided to wear a pair of rather expensive, Aquatilia knee-high gray suede boots with a two-inch heel I found at Saks. I probably shouldn't have bought them, but I just couldn't resist. They were just so pretty and I absolutely loved the way they looked with my jeans and gray sweater. I wore a pair of silver stud earrings and a simple, silver sausage-link necklace along with a silver watch.

We had a representative from the cruise line there to meet us and take us directly to the ship. Once we were on board, a young woman showed us to our cabin. When she unlocked the door and asked us if we had any questions, she said, "I just love your boots!" I thanked her for the compliment and felt a little less guilty about spending $700 for them knowing I would probably only wear them a few times. Our room was a suite which sounds fancy, but in reality, it just means we wouldn't have roommates. It was still very spartan with a tiny shower, toilet and sink, two fold-out beds, a small closet, a desk, a mini refrigerator, and a desk area with a chair. Oh, there was a small TV, as well, but we didn't plan to sit in our room and watch reality shows. But it was there, just in case, you know, we got really bored!

The girl who showed us to our room also told us there would be a bon voyage dinner at 7pm after which we would head out to sea. I asked her how formal it would be and she said, "We have ladies wear everything from formal gown to jeans. Sorry, I know that doesn't help much, but it is the truth." She seemed genuinely apologetic and I understood the dilemma. A lot of women hated dressing up so it wouldn't be smart to mandate any kind of attire even for a formal dinner when the passengers were heading to the ultimate wilderness.

I hated taking off my new boots so soon, but I had no intention of wearing the same outfit to dinner. Besides, I had to strip off the warpaint (ugh!) so I could shave very closely again, then reapply it. Tim wanted to christen our room, too, so that meant another half hour on one of the tiny little beds getting nicely fucked. As much as I wanted that, I was able to talk him into settling for a nice, long blow job with a promise we could make love later that night. He agreed. Gee, what a surprise, right?

Tim brought a clothing bag for us and I had two nice dresses in it along with his suit and a sport coat. I was relieved when I saw they were barely wrinkled at all. I was able to use the steam from an iron to get rid of the few little creases I saw around the waist.

I'd brought the standard little black dress and a beautiful red one. I planned to save the red dress for the farewell dinner, so I slipped into the black one once my hair and makeup were done—again. I loved this dress as soon as I saw it. It had cap sleeves with a large cut out just above my boobs with a smaller cutout above the main one on each side. There was a fairly large open area in back, as well, which meant I'd have to go braless. I knew the adhesive used to hold on silicone breast forms would keep them in place, but it was always a scary thought that one of them might slip or heaven forbid, fall off!

I wasn't worried about cleavage at all as I had become very adept at creating it using a large makeup brush. A couple of swirls and some shading and no one could tell the difference. The dress came to just over four inches above my knee and I was excited about wearing a new pair of 4" black ankle-strap sandals with it. I found them at Express of all places and I was thrilled to pay less than $100 for shoes that would normally cost three or four times the much. I wore a pair of glossy suntan pantyhose with them and I was very happy with the look.

As to accessories, I already knew what I would be wearing. Tim had bought me a gorgeous vintage geometrical pattern diamond bracelet with a matching pendant and earrings. I sprayed on some Ombre Rose, my all-time favorite perfume, and painted my lips a very dark red to match my finger and toenails.

Tim stepped around me and said, "Holy shit. You look unbelievable!"

There was just barely enough room for me to spin around so I did just that. As I did, I tossed my hair and said, "So you like?"

He came over and grabbed me by my waist and said, "Let me show you how much I like."

I pushed him away and said, "Uh-uh. You already had your snack. That's gonna have to last until dessert."

"So are you saying I can have you for dessert?" he said pretending to be hurt from this very serious rejection.

"Uh-huh," I teased. "I promise."

I rarely ever go anywhere without a cardigan sweater, but I knew Tim preferred a bare-arm look. He was so understanding of my insane fetish that I felt like I had to do this for him. I felt almost naked, but I forced myself to tough it out!

I took Tim's arm as we entered the dining room. It was very nicely done with an Alaskan theme of Mount Denali, moose, caribou, and other facets of life up North. I quickly scanned the room and saw several women in cocktail dresses which made me feel much better. There were indeed some older women sitting in jeans and down-filled jackets and that was fine, too. People were paying a lot of money for this cruise so being comfortable was very important.

We were seated at a table with a couple in their mid-50s who were celebrating being empty nesters. They'd married young, raised two kids, and just sent the youngest off to college. This was a second honeymoon for them and the celebration of their 35th anniversary. The man was wearing a nice sports jacket and slacks and his wife was wearing a nice but plain blue dress. Both of them were a bit overweight but who isn't at that age, right? I know my parents had both put on a few pounds before my mom got sick. The main thing was they were genuinely friendly and they seemed very happy.

Ed introduced himself first then introduced his wife, Anna. Ed was a corn farmer from central Iowa and Anna had been teaching elementary school 32 years. "Let me guess. You two are on your honeymoon!" Ed said.

Tim and I looked at one another being he answered for us. "You're the second person to guess correctly. Last time, we were holding hands. What gave it away this time?" he asked.

Anna spoke for him and said, "It's the way your beautiful bride is looking at you. I can just tell. How long have you been married if you don't mind me asking? Ed and I are celebrating our 35th year together on this cruise."

I listened carefully so I could remember the details in case it came up again. Lying can very difficult! "Almost two weeks now," he said as he leaned over and kissed me on the cheek.