A Masquerade - Cover

A Masquerade

Copyright© 2006 by Tom Collins

Chapter 2

Romantic Sex Story: Chapter 2 - Gideon, a gay man, is stunned to find himself falling in love with Emelyne. He's scared, but willing to try.

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Ma   Consensual   Romantic   Gay   CrossDressing   Humor   Anal Sex   Masturbation   Petting  

The next month was slow torture. I spent my days laying around my motel room, or sitting by myself on the bus as we rolled down the road to the next set of shows. I called her from the green rooms or from the motel every night. The sound of her voice inevitably turned me on, and I'd be like a rock at the end of our conversations. I normally shower in the morning, but I started taking them right after getting off the phone with Em so I could jack off without making a mess. She would ask me about once a week if I'd seen any pretty girls. I'd tell her that I had, but that none of them interested me, which was true.

Any time I wasn't on the phone with her, or on the stage performing, I was reading one of several books I'd bought on all the ways to pleasure a woman, and was becoming more comfortable with the idea. Not just of doing it, but of doing it right, so it would be good for her. The strange thing was that it all seemed rather unpleasant if I wasn't directly relating it to Emelyne. Perhaps this was the proof she needed that it was she and not just her body that I wanted, but it made me worry even more. When it came down to the wire, would I be able to perform?

I was anxious to get home, but it seemed that Fate itself conspired against me. Possibly the worst rain and hailstorm I've ever experienced forced us off the Interstate due to a washed out bridge. We had to detour on side roads for nearly a hundred miles, and couldn't do more than forty miles an hour. I'd told Caleb that I'd be home tomorrow, and I still had hope until one of the rear duelies blew. Here I was, stranded in the middle of nowhere, miles from the nearest services, and it was raining like Judgment Day.

I spent about fifteen minutes out in the rain screaming, kicking clods of mud, and pounding the side of the bus with my fists before I'd worked out enough of my frustration to be civil with my busmates. When I climbed the steps, the guys were looking at me warily, never having seen me act like that.

"You need ta get laid, Gideon," Lonnie said.

I looked at him, "Why do you think I'm so pissed about this, Lon? I'm on my way home to see my girlfriend. We'd only been dating for a week when I had to come back on the road, which was just long enough to work up a nice set of blue balls."

"Girlfriend?" Jessie said incredulously, "I thought you were gay, man."

"Yeah, I am. What's your point?" I asked with a grin.

"Oh, I get it..." Lonnie said, chuckling, "He done fell for one of the Trasvestment type girls." Lonnie might be from southern Alabama, but he was amazingly open-minded about most everything. He was also one of the funnies guys I'd ever known and had the 'I'm a dumbassed hick' act down pat. He always managed to sucker Jessie into correcting him because Jessie was a serious pothead, and frequently slow on the uptake. He also happened to be about ten years younger than either of us.

"It's not Transvestment, butthead, it's Transvestite," Jessie said, correcting him for the fifth time today.

"'Er ya sure 'bout dat, Jess? 'Cause I'd'a sworn it was Transvestment. I thought it came from them transformin' they's selves from boys ta girls by changin' they's vestments?" he asked, utterly deadpan.

I was trying to laugh without them hearing because I wanted to see how long Lonnie could string him along this time, but I felt like I was going to bust a lung.

"Nah, man, that ain't—" Jessie saw me out of the corner of his eye and his head turned. He looked at me for a second, as if he was trying to figure something out, turned back to Lonnie and then did a classic double take, his head whipping back to me, eyes wide with sudden realization. "Awww, man, not again! That's it, I'm kickin' yer old ass, Lonnie," he said, as he got up from his seat, "And yer next, Gideon," he threatened, giving me the finger.

"What in hell did I do?" I asked through my guffaws.

"You helped him set me up, man. All that bullshit about dating a girl, that's fucked up, man," Lonnie looked like he was on the verge of wetting his pants.

I got control of myself and said, "I wasn't lying about that, Jess. I really am dating a woman, and she's terrific. Musta caught "the straight" from Lon, or something. I need to call my girl and let her know I'm going to be late getting into town. Excuse me, guys," I said, and moved to the back of the bus to sit on my bed for some privacy.

"Bonjour, chéri, you're calling early today."

"Hey, baby. I've got some bad news. The bus is broke down on the side of the road, and it's looking like we won't be getting in when we thought. If we do get in tomorrow it'll be really late, but I'm betting we won't be in until the day after tomorrow."

"Oh, Gideon, I was looking forward to seeing you tomorrow."

"I know, baby, I was looking forward to seeing you too. I've really missed you, but there's no helping it. The driver's talking to a cop right now, getting him to call a tow truck, but I don't think the tires will be fixed before morning."

"Well," she said with a sigh, "I don't suppose that one day makes a difference in the scheme of things. I was just hoping... that we..." Em's words trailed off, and I knew exactly what she was thinking. I couldn't help chuckling.

"Yeah, I know, baby. I have to confess that I'm pretty nervous about that. It's sort of strange, Em, because when I think about a woman... you know... the uuh... the female parts in a purely generic sense... Well, to be honest, it's unpleasant to think about, but when I think about you, baby, just you in a sort of amorphous way I get hard as a rock in seconds," I held my breath, wondering how she would react to this.

"Hmmm... you're saying that you've become certain that you're not attracted to women at all, but you don't care that I'm one because you want to be with me, the person?" I couldn't decide if she sounded pleased by this.

"Yes, that's what I'm saying, Em. I'm completely taken with you, and gender has ceased to be an issue. I bought a bunch of books so I could teach myself how to make love to a woman."

"Oh God, chéri... you did that for me? I don't know what to say. That's so sweet, so thoughtful. You didn't have to do that, Gideon," she sounded like she was on the verge of tears.

"I did have to, Em. I want it to be good for you. You won't be able to relax and enjoy it if you have to guide me through the whole experience. Besides, I did it for me too. You think I want the embarrassment of being totally ignorant the first time out of the gate?" I asked with a laugh. "That would be a sure way to wind up impotent and incapable of doing it."

"But still..." she said, sniffing loudly and making it clear that she'd been crying, "It must have been very unpleasant. I shudder when I think of the pictures you must have been looking at," she laughed weakly.

"Some of it was, yes, but it wasn't too bad when I related it directly to you. I have to admit that I learned a lot though, and most, if not all, of the positions I discovered in the Kama Sutra would be applicable regardless of gender."

"Is that so?" she sounded intrigued now.

"Yes, there are several that I definitely want to try," I replied huskily. The sound of her voice, so sultry, and the subject matter had my cock throbbing.

"Shit!" she exclaimed, "I'm going to be late for work. I'm sorry, chéri, but I have to run. Will you pick me up for Caleb's party?"

"Uuh... well, I'm not sure that's a good idea, baby."

"Why?"

"Honestly? If I pick you up we'll never make it to the party and then Caleb will be pissed at me because I promised him I'd be there."

She laughed in her usual, musical way, "You're a terrible, wicked man, Gideon. Ok, I'll meet you there then, since you'll be too likely to rip my clothes off if we're alone together."

"You don't know the half of it, baby."

"Stop now... I have to go, and you're deliberately getting me riled. I'll see you at the party, and I'll miss you until then."

"I'll miss you too. See you then." I heard a final chuckle as I pulled the phone away from my ear to hang up.


"Oh, hell no! There is no way I'm wearing that, Caleb!"

"Oh, pleasepleasepleaseplease... please, Gideon?"

"I can't believe you picked out that costume for me. I was going to pick one up today."

"Oh, puhlease! There is no way you'll be able to find anything worth wearing today of all days. Besides, if I let you pick your costume you'll put on a hideous sweater and come as a straight stand up comic. You'll spend the whole party pretending to be a homophobe and telling atrocious jokes. Honestly, Gideon, there's only so many times a person can hear, 'Two fags back into a bar... '" he said. I could practically hear his eyes roll and couldn't keep from laughing.

"Hey, Tony loves that joke."

"Tony smokes too much dope, darling. There's very little left upstairs for him to work with. Maybe we should try to hook him up with that friend of yours, what's his name... Jesse? At least he'd have someone with similar interests to talk to for a change," he declared with a disgusted snort.

"Yeah, you've got a point there, but Jesse's straight."

"Never mind about them right now, Gideon, we're supposed to be talking about you. You'll be the Belle of the Ball in this costume, darling, and we'll be a matched set," he pulled out his big guns, his pleading puppy look; he knew it was almost impossible for me to say no to him when he did.

"The operative word being 'belle'. Why couldn't I be Robin?"

"There weren't any Robins left. All I could find was this one and Will."

"Then I'll be Will."

"That won't work, darling. First off, the costume is sized for me, not you, and secondly, Will was a fop and you could never pull that off."

"But I could pull off a woman?"

"If you're in anything resembling pants you'll keep acting butch. With you dressed up like Maid Marion, you'll be in a dress, and that will keep you in character. Please, Gideon?" he pleaded, giving me that look again and cuddling up to me. "I don't want to be Will on my own, and I couldn't find any other Robin Hood character costume that would fit you. You're very average sized and all that was left were oddball sizes, either way too large or far too small."

I growled in the back of my throat, "You're such a passive aggressive bully."

His whoops of elation almost made me smile. He spent the next four hours doing truly heinous things to me. Waxing and shaving hair, putting weird, smelly stuff on my face then peeling it off, pinning my hair down under a skull cap. He loved every minute of it and I hated it. By the time he was done, I looked nothing like myself. The corset was killing me, but there was no getting around it since it was an integral part of the costume. He'd at least been kind enough not to pull it too tight, so I wasn't having too much trouble breathing.

I spent the next hour alternately watching television and his progress in getting himself ready. He certainly looked the part in his scarlet silk costume, lace hankie and crossed swords on his back.

As we set out the last of the starter hors d'oeuvres, the doorbell rang for the first time. I was fighting with the veils on my stupid hat when Caleb came bouncing back in with Adrien and Howie dressed as Catherine and Heathcliff from Wuthering Heights. Every year those two would pick a different classic novel; Adrien always took the female part because Howie refused to wear a dress. I knew I'd be catching serious shit from him over my costume. The look on his face when I sauntered over to him, batting my fake lashes, was almost worth the jibes I'd be getting all night.

"Something's wrong with this picture," Adrien said, looking between Caleb and I.

"Tell me about it. I'm too butch to play a queer, apparently. I think he just wanted an excuse to make my shave my pits," I responded, raising my arm to show them my denuded underarm through the slit in the sleeve.

Howie immediately started laughing. I rolled my eyes heavenward, and went into the kitchen to get the huge, punch bowl, cups and ladle for the Sangria.

After the first two, people started arriving in large groups or trickled through the door in ones and twos. All of the costumes were flashy and wonderful. The strangest set of costumes that I saw was on Jesse and Tony. It seemed they'd met at one of our shows a month ago and Tony invited Jesse to the party then. They'd apparently gotten together earlier over at Tony's place, painted each other olive green with red and brown streaks, including they're jockeys, and then wrapped each other in yards of cellophane. When questioned they proclaimed that they were quarter ounces of Acapulco Gold and Thai Stick. Getting him alone for a minute, I asked Jesse if he realized that Tony probably considered they were on a date. Jesse said, "Don't worry about it, man, he's cool. Do ya think he'd hook me up if I let him blow me?"

"Probably not, but he might if you blew him," he made a face.

"Blech... I'd rather fuck 'em."

"What? I thought you were straight?"

"Hey, man, a hole's a hole, and we're talkin' about weed. If doin' a hole gets me a new connection for primo shit then I'm there, man. And don't fuckin' look at me like that, Gideon. I know what yer thinkin'. That it's cold that I'd use him like that, but he'd be usin' me just as much. It'd be a symbiotic relationship; ya dig? I'd be getting' what I want, he'd be gettin' what he wants, we'd both have a new buddy and everybody'd be happy."

I just shook my head and went back to mingling. Finding Tony at the wet bar, I thought to warn him about Jesse. They were both my friends, but I'd known Tony a hall of a lot longer. His reaction shouldn't have surprised me, I suppose.

"No shit? He told you that? Wow, thanks for passing the word, Gideon, you're a true friend. Gonna get some tonight," he practically sang the last sentence, and started whistling Mack the Knife as he grabbed their drinks and headed for Jesse. Again, all I could do was shake my head in astonishment and circulate some more.

Sylvia, a transsexual who'd yet to see the sharp side of the knife where the 'boys' were concerned, had a perfect Dolly Parton going. The enormous breast implants and equally huge, blonde wig definitely helped, since they made it difficult to focus on anything else; the effect was almost hypnotic. I was chatting with her about how uncomfortable my corset was when I heard the distinct sound of Em's laughter behind me.

I turned just as she said, "Oh my God... I can't believe he got you into a dress." I froze when I saw her.

"That little bitch lied to me," I said indignantly, "He told me he couldn't find a Robin Hood costume when there was no way he'd have gotten me one if he could because he knew that's what you were coming as. You two planned this between you, right?" I took her in, and caught myself faintly wondering which the illusion was, the man standing in front of me, or the woman I'd kissed on the Ferris Wheel.

She crossed the ten feet separating us, "No, chéri, I had no idea what costume he would pick for you. He asked me what I planned on coming as and I told him I was going to be Errol Flynn in his role of Robin Hood. I actually expected him to get you Will Scarlett, or maybe Little John. This never crossed my mind, I swear."

"He's a twisted, little shit. He's playing Will tonight," I said, pulling her against me and seized her mouth for a hello kiss. Holding her tightly, caressing her back, I decided that I liked the way she felt without a bra breaking the smooth lines of her spine and ribs. ¬I was nearly lost in her taste when Sylvia violently cleared her throat to get my attention.

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