So Close to Heaven

This story is also told by Selina.

The brothel was clearing out. There was no one in the make-out room. Only a few bodies remained on display in the objectification room.

The orgy room was the place to be.

“I guess things wind up kind of early, huh?” I asked Lolita as I held open the door.

“Jefferson, it’s after three,” Lolita replied. “I mean, seriously, what do you want?”

In a far corner, a man massaged a woman’s feet. I exchanged waves with the Tantra instructors who fucked among the couples on the mattresses.

Selina had set up camp in the orgy room hours earlier. I checked on her throughout the night as I made my rounds and she worked through a retinue of her admirers. She kept busy despite having decided to forgo sex for the duration of the weekend—or rather, to forgo vaginal or anal penetration with “bio cock,” as male genitals were dubbed at sex camp.

Of course, genital intercourse is the first thing most people think of when referring to orgies, but, as Selina knew, fucking is merely scratching the surface of sex. While removing one item from the agenda, Selina retained many creative alternatives.

“Having fun?” I had asked her as man licked mud from her spiked heels.

“How’s it going?” I had asked her as she blew two men at once.

“Holler if you need anything,” I had offered as she spanked a bad boy.

Now, Lolita and I found Selina nude in the orgy room and talking with a well-dressed blonde. Her new friend was tarted up in black, from her high heels and hose to the dropped neckline of her short black dress.

“Jefferson!” Selina called. “Come here, I’d like for you to meet someone.” She smiled as she turned the girl to face me. “Lolita, Jefferson, may I introduce Windsorina?”

“Pleased to meet you,” Windsorina smiled, shaking strands of hair from her rouged cheeks.

Well, shut my mouth, I thought.

It was Windsor, the fellow who had followed Selina like an adoring puppy since she arrived at camp, now recreated as the fetching Windsorina. The previous evening, he had confessed to us his fantasy of being transformed into a girl. Now, it seemed that his fantasy had been realized.

“Pleased to meet you, Windsorina,” I said, taking her hand and kissing a cheek freshly shorn of its goatee. “It’s hard to believe I’ve missed such a pretty creature all evening.”

Windsorina looked down and blushed. “I’ve been here . . .” she began.

“When you took Marcus to the hospital, Viviane and I discovered Windsorina,” Selina explained. “She was hiding, but we uncovered her. All it took was some makeup, some clothes, a wig . . . and there she was.”

“Really? So Windsorina was dressed by two women? Why, if I recall correctly, that was precisely her fantasy.”

“Yes, well, that was half of her fantasy,” Selina grinned. “I need your assistance to fulfill the remainder.”

“What’s the fantasy?” Lolita asked. Selina raised a finger to her lips.

“I’m happy to do my part,” I said, chucking Windsorina’s chin. “I’ll do what I can to please this beautiful creature.”

Again, Windsorina turned her face. Her modesty was enchanting.

“Windsorina, turn around please,” Selina instructed. Windsorina complied, turning awkwardly on her heels. Selina reached around her charge’s waist, slightly raising her black skirt to reveal a buttock. “Isn’t that a lovely sight, Jefferson?”

“Indeed it is,” I agreed, raising my hand. “May I . . .?”

“Yes, please,” Selina offered.

I reached forward to caress Windsorina’s ass, feeling its curve in the palm of my hand. “So soft,” I admired. “And so smooth. May I spank her?”

“Yes, of course,” Selina said.

I gave Windsorina a few light slaps. Her flesh pinkened to a light rosy hue.

“She’s lovely,” I admired. “I think I would really enjoy some time with Windsorina, if that’s all right?”

“I think Windsorina would like that, wouldn’t you, Windsorina?” Selina asked. Despite the sweetness in her voice, Selina’s tone suggested that this was more a direction than an inquiry.

Windsorina looked to her mistress, then down to her heels. “Yes, please,” she nodded, her voice barely higher than a whisper.

“I’m delighted,” I smiled. “Let me help you to your knees, Windsorina. Let me see how well you suck cock.”

Windsorina looked in my eyes, and then averted her gaze as she took my hand. Gingerly, she lowered herself to her knees, her skirt rising slightly on her thighs.

I unzipped my shorts and dropped them to the floor. I stepped from them as I removed my shirt.

Selina took Lolita aside to explain Windsorina’s fantasy. “She wanted to be dressed by two dommes, then made to service two men,” she said.

“Oh, a forced feminization scene. Goody!” Lolita grinned. “Then we’ll need Marcus for this. I’ll go find him.” She smiled at me before leaving.

I smiled back, then turned my attentions to the quiet blonde kneeling before me. I traced my cock along her lips, gently smearing her bright red lipstick.

“Part your lips for me, pretty Windsorina,” I directed. Windsorina looked at my belly, her face slightly panicked.

“Eyes on mine, pretty girl,” I said, taking her chin in hand. “Eye contact greatly enhances a blowjob.’

With her eyes on mine, my cock slid slowly into her mouth. I moved my hips slightly, gently fucking the top of her tongue.

“Now, move your tongue on me,” I directed. “Let me feel your mouth come alive.”

Windsorina’s tongue moved tentatively around the head of my cock.

I looked to Selina. “The girl’s obviously a neophyte, but she’s got some abilities. I think she’s worth the training.”

“By all means, please enjoy her,” Selina said. “Anything you can do to further her training would be great.”

I looked to Windsorina. Her eyes blinked as she twirled my cock in her mouth. “Your mistress is very gracious,” I smiled, petting her hair. “You are a very lucky girl indeed.”

A hum of assent murmured under her Adam’s apple.

I took her cheeks in my palm. “I think you should honor her by being a better cocksucker,” I said, easing myself deeper into her face. “You suck cock like a girl, and that really won’t do.”

She gagged as I reached the back of her throat. I held her face in place. Her eyes widened as she struggled for breath.

I pulled my cock from her mouth. I took one hand from a cheek and slapped her. “Like a girl,” I repeated. “That’s not good enough. Again.”

I parted her lips with my cock and slowly edged it into her mouth. “Relax,” I told her. Windsorina drew a breath through her nostrils and swallowed as my cock edged to her throat.

Again, I held her face in place. This time, she held her own.

“Good girl,” I commended. “Now, you can better service me.” I swayed my hips, moving myself back and forth into her throat.

Windsorina sputtered as she struggled against gagging.

“Just relax . . .,” I repeated, fucking her. “Let me do the work.”

Windsorina blinked and drew a deep breath. I held her face in place and fucked her mouth as softly as a lullaby.

“Hey Jefferson,” Marcus said. Lolita held the door as he hobbled into the room. “Selina, how’s it going?” He moved to lean against a post, taking the crutches from under his arms. He waved to the Tantra couple. “You two are too gorgeous,” he smiled.

Marcus began to undress. “Lolita says you might need a little help, Jefferson. Who’s the girl?”

I held her chin, turning her face slightly without removing my cock from her mouth. “This is Windsorina,” I said. “Windsorina, this is my friend Marcus.”

Windsorina gurgled.

“’Windsorina?’” Marcus asked, stepping from his pants. He turned to Selina. “Why not just ‘Wendy?’”

Selina moved her hair from one shoulder to another. “I think ‘Windsorina’ is a more feminine name,” she asserted.

“Well, she’s your project,” Marcus said. “I’d have gone with ‘Wendy,’ but whatever.” He looked to the Tantra instructors, bringing his hand to his hardening cock.

The man looked back at Marcus and smiled as he watched him stroke. He intensified his thrusts into the woman under him.

“So, is she much of a cocksucker, Jefferson?” Marcus asked, never looking away from the couple.

“Serviceable, at best,” I replied. “She needs a little guidance.”

“Ugh,” he complained, looking to us, then back to the man watching him. “I’d really rather get good head. This could be more trouble that it’s worth.”

“She’s not much, but she is on her knees,” I pointed out. “You want to give her a try?”

Marcus turned and watched my cock glide between red lips. “All right, whatever,” he said. “But move her over here—I need to lay back on this mattress.” He positioned himself so that he could see the Tantra instructors. “Be careful of my knee brace,” he told Windsorina, barely looking her way.

I took my cock from Windsorina and offered her my hand. “Stand up, pretty,” I said. “I want you to blow my boyfriend. Treat him as you have treated me.”

Windsorina stood cautiously on her heels. She moved to kneel before Marcus. He spread his legs and positioned himself at the edge of the mattress to accommodate her.

“Please, don’t fuck this up,” Marcus said, stroking his cock to its full length. “If this isn’t good, I’m kicking you off my dick.”

“I’ll do my best . . .” Windsorina began.

“Shut up, shit,” Marcus said, cutting her off. “Shut up and suck my dick.”

Windsorina lowered her mouth to take Marcus. Her blonde wig bobbed up and down as she gasped for air.

“Jesus, you’re a mess,” Marcus said. He put his hand on her head and held her down. “Just focus, okay? Just take it all and focus.”

I looked to Selina. “I think he’s having the same trouble I was,” I said. “The girl needs to work on her concentration and stamina.”

“I can see that,” Selina nodded. “Duly noted.”

I caressed Windsorina’s soft black dress. My hands took her hips firmly. “And she’s an ass virgin?”

“Yes, I believe so,” Selina said.

Windsorina gasped in the affirmative.

“Shut up,” Marcus said, taking her cheeks roughly. “No one’s talking to you.”

“Hmmm, well, I’d like to fuck her virgin ass,” I said, reaching for her panties. I pulled them gently over her ass and down to her knees. I lifted each leg to move them as far as her ankles.

I let the panties rest there, as they looked nice with her hose and heels.

I moved to the shelves near Lolita to find a condom and lube. She took my cock in her hand.

“This stuff really gets you hard,” she grinned.

“Shh, don’t tell anyone,” I smiled. I kissed her. “So this will be, what? The third person you’ve watched me fuck tonight?”

“Yeah, and it’s giving me ideas . . .” she said.

I nuzzled her leather motorcycle jacket. “Any ideas you get, I’m your man.”

We kissed again. She ran her grip along the shaft of my cock.

“Go,” she said. “You’ve got ass to fuck.”

“Oh, right.” I kissed her cheek and toyed with her hair. “You’re cute. Here, open this condom, would you?”

I rolled it on my cock as I walked back to Windsorina.

“Fuck, look out for my knee,” Marcus said, slapping the girl on his cock. She gurgled an apology. He slapped her again. “And shut up. Damn, you’re really starting to piss me off.”

“Hold her steady,” I said, lubing Windsorina’s hole. “We’re going to spit roast her—you sticking her top, me sticking her bottom.”

“Geez, Jefferson, you’ll fuck anything.”

“This is a favor for Selina,” I said. “And anyway, I’m a sucker for virgin ass.” I added more lube to my hand. I slathered my cock, slapping Windsorina’s ass to wipe away the excess. I spread her knees as far as her restrained ankles would allow.

I crouched behind her, my cock poised at the ready. “All right, pretty baby: I’m taking your ass.”

“This will hurt at first . . . “ Marcus said.

“ . . . but I will push ahead,” I added.

“That’s the best way,” Marcus finished.

I began to ease the head of my cock into her. My cock bent back.

I looked down and placed my thumb against her hole. I gently eased it in. Windsorina fell forward slightly.

“No, no,” I said, pulling back her hips. “You need to be brave and stay steady, darling girl. That will make this go much more smoothly.”

I repositioned myself to try again. I pushed forward only to feel my cock slide between her cheeks.

“Shit,” I muttered. I crouched a little higher and spread her ass. Again, her hole turned me away.

I looked at Selina. “I can’t get in there. She’s too tight.”

“Hmm, well, let me help. Maybe she’s tense.”

Windsorina gulped. Marcus sternly told her to focus. He caught my eye and raised an eyebrow. I shrugged.

Selina knelt beside her charge and lubed her hand. She massaged Windsorina’s hole with one hand and rubbed her back with the other, offering words of encouragement.

“I do love boy ass,” she whispered to me.

After a time, she took my cock and tried to guide it into Windsorina.

Once again, my cock was rebuffed.

Selina looked at me. “Wow, she really is tight.”

“This calls for serious action,” I said, standing.

I retrieved a glove and more lube. I knelt behind Windsorina, gloving my hand and covering it with lube.

“Here, try more lube,” Selina offered, holding out a bottle.

“Good idea,” I said, as she poured it onto my glove.

My hand dripped as my finger entered Windsorina’s ass. She flinched, but relaxed at the sound of Selina’s voice.

“Tight?” Marcus asked.

“If she sneezes, she might break my finger,” I said.

Soon, between the three of us, we opened Windsorina. I got two fingers into her, allowing the leverage and penetration needed to get deep into her while coaxing her prostate.

I wanted to try once more to get my cock into her, but I had my doubts. If I could get her to shift position, it might work. But that could require moving Marcus, which would be disruptive, given his carefully positioned leg. I could ask her to stand, but Windsor was taller than me, making it hard to get my dick to the height of his ass. Never mind Windsorina’s heels, which would raise my destination into the stratosphere.

At any rate, there was no need to shuffle this configuration of bodies at the risk of losing this moment. Windsorina was finally in a proper frame of mind. Her cocksucking grew more intent; Marcus was now able to “kick back,” as he says, and enjoy his blowjob without issuing reprimands.

“You are doing so well, Windsorina, so well,” Selina softly intoned. “Such a good, good girl.” Selina reached under the girl’s spread legs to massage her cock.

We soon felt Windsorina’s body melt in orgasm.

“Yeah, give it,” I barked.

“Cum, damn it,” Marcus ordered, wedging his cock in her throat.

“Such a good girl, a good, good girl,” Selina cooed.

We helped Windsorina to her feet. Her makeup was smeared and her eyes glazed with pleasure. Selina embraced her, telling her what a good, brave job she had done.

Marcus kissed her cheek. “It wasn’t the worst blowjob I’ve ever had. It got much better as you progressed. You just need to keep practicing.”

“Thanks,” Windsorina beamed.

“I have to confess, I was skeptical,” I said. “When you first told us you had a fantasy that would take all four of us to fulfill, I thought you were dreaming. But now, thanks to Selina, your dream came true. You were feminized by two women and forced to serve two men. You did it!” I kissed Selina. “You must be very proud.”

“I am,” Selina nodded earnestly, rubbing Windsorina’s back. “She did very well. I am honestly very impressed.”

“I was a little afraid,” Windsorina said. “I really felt scared when you started to, you know, fuck me. But then it felt so good, I had to let go.”

“Oh, I didn’t fuck you,” I corrected. “That was my hand.”

Windsorina’s smile fell.

“But you did a great job,” I hastened to add. “You took practically the whole thing. And I’ve got huge hands—see?” I held out a hand. “Huge.”

She looked crestfallen. I regretted having said anything; it just slipped out, as the truth so often will.

“You did a fine job,” Selina repeated.

“You sure did,” I nodded. “Just think: you were so close to heaven.”

Windsorina looked at Selina and smiled at that thought.

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