CHAPTER 10

One of the advantages of Monterey, from a single girl standpoint, is the availability of men. Single, horny, attractive, straight men. This is partly because of the military presence: the Naval school and the adjacent Army Language institute has a large population of military guys, mostly ranging from 18 to about 35. Being military guys they are all in good shape; some, frankly, are absolutely gorgeous hard-bodied studs. Being military, they are clean and drug-free and relatively well-behaved... And since they are attending schools most are there on 1 year assignments, away from home, and you know what young studly guys are thinking about in a resort town away from home, don't you? Well, I do, anyway. And if I didn't before, I sure do now. 

OK, I know what you're thinking... relax. I knew the straight part of the available male population was going to be a problem. I was going to have to have a method to overcome (no pun intended) any initial shock at finding out their new girlfriend had a penis of her own. I figured the best way was to go after the younger guys... the young enlisted men, away from home for the first time in their lives and desperately aching with teenaged hormonal lust and all the energy of hard-bodied boot-camp graduates who hadn't seen many women in several months. There was already a culture of sex about the place: the language institute, whose initials were D-L-I, was known as the "Defense Love Institute" for the high rate of sexual shenanigans and the pregnancy rate among the young female service-members. Given all that, I figured that if I got some young teenage studs horny enough (which shouldn't be hard - again, no pun intended) they would just fuck any part of me I put in front of them and not worry about details until later... when I could just play on their hormone-addled emotions. 

Now, being a resort town, Monterey has a lot of hotels. One of the biggest and best is a resort and convention center right in the center of town, on the bay itself. Conveniently it had three things I wanted: a bar, a parking garage, and walking-distance proximity to both the naval school and the language institute. 

I considered my look carefully. To be honest, I was a bit worried about the long-term consequences of promiscuity. I was planning to live here for a while and I didn't want my phone number being written on bathroom walls or young studs stalking me or anything like that. I had to have some anonymity. So I made some notes... it occurred to me as I did so that I could use the opportunity for a little mild role-laying. You know... different sexual archetypes. I outlined a few for myself. They had to be deniable... by which I mean that they would have to change my look just enough, and not excite attention or undue interest so that I could conveniently disappear. Naughty Naval Officer was out, for now anyway I thought wistfully. That would have to wait for duty. I savored the thought for a moment. I was looking forward to making my firm little ass, pert breasts, and pouty lips available in my cute new Naval Uniforms to hard-bodied and horny military studs. I thought about Pete... and my next-door neighbor, Mark... I thought about both of them in uniform and me in mine, me bending over between them with Pete in my mouth and Mark up my ass... I shook my head clear of the daydream. Back to work, I told myself sternly. (But I really was looking forward to bending over and taking it in my ass with my cute little white uniform skirt up around my waist... and a mouthful of cock and cum at the same time would be a nice little bonus if I could figure out a way to work it.)

I focused on the present with a bit of an effort and tried to think of ideas with a little more anonymity. Professional-looking business-woman. Prim & proper repressed librarian or school tacher. Bored sexy housewife. Artsy and kinky goth-chick. I didn't want to look like a hooker... I didn't want to get arrested, after all. But I had to be sexy in a way that would get the attention of horny teenagers. So I thought about it carefully and decided on my first foray into anonymous sex. First, I put on some sweats and a t-shirt and went to the drugstore, where I bought some black washable hair dye and some non-prescription reading glasses with black plastic frames and a stylish retro-cats-eye shape. When I got back I spent an hour or so rinsing my hair and dying it with the temporary hair dye. Then I sat for a while and applied makeup... not too much, but I wanted to make a statement, so my foundation was a bit more pale and my lipstick was a bit more bold and bright red than usual. I spent some time outlining my eyes and lengthening my lashes to make them look big and wide (and, incidentally, different from my usual classic-elegant or natural-with-a-hint styles). Just a hint of blush to accent my cheekbones... and a few strategic dabs of perfume. I topped it off with black stud earrings, a black bead necklace, and I combed my now-black and still-damp hair straight back in a severe style and added little bright red flower-shaped barrettes on the sides for accent. 

Next I got dressed. I had decided to go for the artsy goth-chick look for my first little foray.  First, though, I prepped myself for what I was hoping would be a night long ass-fucking: I got my butt plug, lubed it and my ass, and stuck it in my anus... oooh, that felt good. I savored the sensation as it stretched me, getting me ready for the night. Then I started dressing with the lingerie: a red satin waist cincher with garter straps attached to seamed nude silk stockings with red toes, Cuban heels, and a red welt at the top, over which I added red satin high-cut panties with black lace detail and a matching red-satin push-up bra with a black-lace brocade pattern. Over this I put on a bright red silk blouse with a high mandarin collar and short sleeves, a tight black pencil skirt in a delightfully clinging wool-spandex blend that came to just above my knees, and a short black jacket in buttery-soft leather. I added shiny red patent open-toed leather pumps with daring 3 ½" stiletto heels... and wrist-length red leather gloves in soft, supple kidskin. I checked the mirror. Perfect. With the glasses and an appropriately serious expression I looked pale, sexy, and severe. The deep red lipstick and black jewelry made a dramatic contrast with my smooth, creamy, pale skin. I threw toiletries and a hairbrush, some makeup, a short apricot silk nightie, some sweatpants, a hoodie, socks, sneakers, and a t-shirt in an overnight bag and headed for the convention center. I paid for valet parking and headed for the lounge. 
It was just after dinner and the lounge was just getting busy with the Friday-night crowd of young singles and middle-aged hopefuls. I found a stool near the end of the bar and perched daintily with my legs crossed and one spike heel hooked on the stool shoe rail and pretended to examine my mp3 player. I didn't have to buy a drink... three arrived fairly quickly, from three different men each hoping to catch the attention of the cute goth chick. I ignored them, sipped on the drink I liked best, and waited to see who would take the chance first, and if he would catch my interest. I didn't have to wait long. One sat down next to me. 

He was a young stud all right. He couldn't have been more than 22... to be honest I'd have thought him younger, except here he was in a lounge, sending me drinks, so he at least had to be 21. But, young though he was, he was huge and black and was so muscular he looked as if he was chiseled out of mahogany. I tried no to visibly drool at the sight of him, but a little surge of thrilled fear and desire shot through my groin. Oh, he was the one all right. But I had to play this just right if it was to work out the way I wanted. 

"Hi," he said, a bit shyly. 

"Hi," I said back and looked at him coolly over my glasses.

"Um... do you like the drink I sent you?"

"You mean this one?" I raised the glass I had been sipping on and arched an eyebrow. He nodded. "Yes, thanks." He looked like he was trying to think of something to say next. I decided to help him out a little I was feeling hornier just looking at this big stud struggle boyishly with indecision. "You know," I said, smiling, "if you want to meet me, all you have to do is say so... you don't have to come up with some silly come-on line." 

He smiled in relief and blushed about two shades of deep purple. "Oh, sweet!"

He paused, and then blurted, "a lot of chi... uh, girls, they get all, well, you know... I mean, they want to hear stuff that's all original and shit." 

"Well, I like stuff that's all original and shit, too, it's just easier to get to if you're honest upfront, don't you think?" 

"Uh, sure! Um... my names Daryl," he said, putting his hand out. I took it. It was a lot bigger than my soft little white hand. He wrapped his fingers around my hand, gently, as if he was holding a kitten. His hand was warm and hard. 

"My name is Wendy. Are you from Monterey?"

"No, we're stationed here... we're Marines, we're going to school at the Language Institute right up the street." 

"Oh, wow... I never met military guys before. No wonder you're so ripped." He looked smug at that. "Where's the `we' you were talking about?"

"Oh, that's my buddy, Jason... he, uh, bet me I couldn't get you to come and hang with us." He pointed at another guy, this one white and blonde, sitting at a table across the room and trying to act like he wasn't watching.

"Oh, he did, huh? Why me? And... what do you get if you win?" 

"We figured you was the hottest chi... uh, girl here, but he said you were probably stuck u... I mean, the kind of girl who probably wouldn't hang with military guys." 

"You can say `chick' if you want... I don't mind." He grinned and blushed again. It was adorably sexy. I really wanted him. "And your prize if you win?" I reminded him. 

"Oh, he has to pay for the bar tab all night." 

"Does that include guests?" I asked sweetly.

"I guess so..." the light came on. "No way! You'll come over?"

"Sure," I said, standing up, dropping my mp3 player in my handbag and picking up my drink. "Why not? Drinks are always better when somebody else is playing. Let's go spend your friend's money." I took his arm, which felt like it was carved from wood, and we walked over. Jason was standing up looking surprised as I said by way of greeting, "looks like you lose your bet!" as I sat demurely and crossed my legs, facing him at slight angle so he could admire my long smooth calves and my dimpled knees. 

Jason got over his surprise soon enough, and Daryl and I ordered more drinks on his tab and chatted and drank, and ordered more drinks, and chatted some more. I told them I was a graphic artist (which sounded nice even if I didn't know a thing about it) and on a business trip here from New York; they told me there were both fresh out of Boot Camp, where they had met and become best friends, and that Jason was from small town Wisconsin and Daryl from Detroit. Neither had steady girlfriends, or so they said ostentatiously, several times to get their point across. I wonder if they have some girl in mind, I thought to myself facetiously as I noticed Daryl gradually moving his chair closer to mine, and Jason trying to touch my hand and "accidentally" brush my leg with his. As they had more drinks they started competing for me, which I simply adored, basking in the warmth of their testosterone-laden attention... they had each had enough that their stories were becoming more sexual and suggestive, which I responded to by paying attention to the other guy as each told them, just to fire them up some more. As they started to snap at each other in their frustration I decided now was the time to spring my "surprise" on them. The room was fairly full, so if they reacted better I'd at least have some witnesses and, hopefully, some rescuers. I took a deep breath as the two friends glared at each other in their frustrated male competition like two dogs sniffing each other and about to start growling. 

"Hey...," I said. They both looked at me. "I'm having a good time and all, but if you two studs are going to beat the shit out of each other over me there are two things you should know." They each visibly sat back and relaxed a bit, glancing at each other out of the corners of their eyes. 

"What?" said Jason, as Daryl said over him, "she's probably married or some shit." "Shut up, man," said Jason. "What," he repeated, looking at me with his big blue eyes, serious again.

"I used to be a man," I stated simply and quietly. I prepped myself mentally to run for it if it looked like they were going to get violent. There was a long moment of stunned silence. 

"What?" said Daryl, as Jason blurted, "No way!" 

"You heard me," I said. "I know you guys have been coming on to me and all, so I figured I give you a chance to walk out before you did anything you might think was... embarrassing. But if you're going to get violent," I warned as they sat back with stunned expressions, "I swear to God I'll scream and have you arrested for assault, so don't try any shit. Now do you want to hang some more and have a good time, or should I just go?" I added the arrest bit, knowing they knew they'd be snuffing out their nascent military careers before they had even begun if they were brought up on civil assault charges, regardless of the circumstances. I waited a bit. Nothing. I sighed theatrically, and stood up. "OK, have it your way." I started to walk to the door. I hoped one of them, at least, would come after me. As I walked further my heart sank. Damn. I was hornier than shit and it hadn't worked. 

I was almost to the exit from the hotel lobby and feeling pretty sorry for myself and extremely frustrated all at the same time when a hand gently touched me on the arm. I started and turned in surprise. It was Jason, looking sheepish. 

"I... uh... I'm really sorry about that. I mean, it was kind of a big surprise, ya know? Uh... we're both sorry," he added, "but Daryl is still kind of getting used to it. He's OK," he added in a rush," it's just a little tough for him, I guess." 

"So?" I said archly, crossing my arms and tapping my toe.

"Um... please come back and sit with us? We're cool, really." 

"OK," I said, slowly, leaning forward to him. I could see him take a deep breath and his fair skin colored a little as he breathed in my perfume. I added in a fierce whisper "but if you try any crap on me, and I'm out of here!" 

"Hey," he said, placating as if he was talking to a frightened child, "it's cool, really! Daryl's a cool guy; he just never met a tranny before." 

"Oh, and you have...? And get something straight, Mister! Don't call me that! I'm a woman. What I used to be doesn't matter, except that I wanted to be honest with you two assholes. I'm a woman, not some fetish freak. Get used to that!"

"Oh, jeez, I'm sorry," he blurted. "Oh, man... look, I didn't mean to make you mad, its just that I've seen some girls... er... chicks... like you online and I thought they were just as hot as ... um... other women, you know?" 

"I am not your personal porn jerk-off photo," I said coldly. 

"Oh, shit, I'm really fucking this up..." He looked genuinely crushed. I decided to let up on him a little. This might just work out, yet. "Look," he said, sounding desperate, "I don't want to make you mad, it's just that I think your hot, and Daryl does too, and we were having a cool time and everything, and Daryl and me both want you to come back and hang with us and maybe have a couple of drinks or go dancing or something, OK?" 

"OK," I said, after short pause, and gave him a little smile. "

Let's go back and see what Daryl thinks about it."

Daryl had apparently had some time to adjust because he jumped up and held m chair for me as I sat. I looked up at him. "Are you OK with me?" 

"Oh, hey, baby, I'm real sorry..." he said, slowly and softly, looking down. "Jason, he's better at explaining shit than me." 

I let them both explain for a while longer, Jason more talkative but making gaffes and Daryl almost shy now, almost hesitant to look at me. We had more drinks... and more... and they started to loosen up again and the sexual innuendo started up again. I noticed they carefully avoided anything to do with my little `difference' though. 

"Do you want to know what the other thing was?" I asked after I went to the ladies room and came back. I found they had moved their chairs close enough that Daryl was able to `casually' put his arm around my shoulders while Jason's hard thing pressed up against mine in its tight skirt and his fingertips lingered gently on my silk-covered skin just between my knee and the skirt hem and decided now was the time. 

"Uh, what other thing?" Jason asked softly, leaning close so that his breath tickled my ear. I felt goose bumps at the sensation; I was tingling all over from their closeness and their deep, salty male scents. 

"The other thing I said you should know about me," I purred, softly. "I think you may like this one better than the last one."

"Um, OK," said Jason, sounding a little worried.

"I don't mind sharing... or being shared." I let that hang for a bit. 

"Uh, what?" Jason sounded like he couldn't believe his ears. Daryl just looked stunned. 

"I mean," I said coquettishly, "that you don't have to compete for me. If you want we could all have a good time together tonight... that is what you were thinking about when you started feeling me up, wasn't it?" 

The alcohol was clearly lowering their homoerotic inhibitions. They didn't even look at each other before they both blurted "Oh, wow, yeah, sweet!" and "shit, yeah, baby!" over each other. 

"Well," I purred softly so they had to lean close (which is what I had in mind), "One of you guys could get a room while I go to my rental car and grab one or two little things for overnight..." I turned my head and nuzzled Daryl's neck while I stretched out one long silk-clad leg so that my skirt rode up and guided Jason's hand to my smooth silk thigh and the teasing hint of red silk stocking top. After a few seconds of this, as Jason was trying to get his hand up my tight skirt and Daryl was trying to feel his way inside my jacket, I broke off and grinned. "I really think we should get a room before somebody throws a bucket of cold water on us! Meet me in the lobby in 10 minutes?" 
They were breathing hard, but looked sheepish and meekly shuffled off to get a room while I went to the parking garage and got my overnight bag. This was going great so far. 

My heart was pounding in anticipation and I was almost panting on the way back. I stopped in the lobby ladies room before I get back to the main lobby, and went in a stall. I hung my bag on the hook and quickly undid the waistband of my skirt and pulled it and my panties down. My little cock sprang out, but I pushed it back between my legs with my hairless scrotum and fished my tube of lubricant out of the bag. I pulled out my butt plug and wrapped it in toilet paper and stuck it in one of the bag pockets; then I quickly re-lubed my ass which was good and loose now, pushing a good amount inside me and smearing the rest up and down my ass crack; then I wiped my hands on toilet paper and pulled my skirt and panties back up. Leaving the stall I washed my hands and headed for the lobby. There they were, waiting and looking anxious. Well, that's how I was feeling too. The elevator ride to the 4th floor was silent... we were all nervous, for our own reasons I suppose. 
