Her Whipping Boy

Elliot warned me before he left for the summer. "My sister is totally gay, like lesbian." He only had a moment to chat over the three-foot-high chain link fence separating my yard from his parents' yard, the swimming pool behind him reflecting the sun. She'd just returned from a college exchange program in Paris, he explained, and intended to hang out by the pool for July while she pondered what to do now that she had her degree.

That was all he had time to say before he wheeled his suitcase out to the driveway to catch a ride from his parents to Bar Harbor. He'd unexpectedly landed a job on one of those big cruise ships that make their way from New York up the coast to Nova Scotia and back. Elliot would be gone all summer, which dashed our plans of making out over and over again in my basement. Since he considered himself "75% straight," I would put money down that a hot looking twink like him would get laid with both sexes all the way up and down the east coast. It was an awesome job for someone with only one year of collage left, a total party-work balance.

Since he and his parents knew I was gay, I was surprised that Elliot felt he needed to give me this warning about his older sister. I understood better later that afternoon when a splash in their pool caught my attention. I looked up from my computer and out my home-office window on the second floor of my house.

Wow! She climbed the ladder from the deep end, dripping and hot, in the smallest of bikinis. Like Elliot, she had very red hair, cropped boyishly short yet with a funky style, much shorter on one side than the other. Her breasts weren't big, but they were high and shapely, her cleavage deep and alluring. It's a good thing I'm gay, or I'd have found her very distracting, and I had a lot of work on my plate. Still, I admire female beauty like fine art.

Yet, over the next week, I found myself frequently drawn to that window. Like Elliot, she liked to spend a lot of time in the backyard wearing next to nothing on warm days. She even mowed the lawn in her bikini, although she wisely sported steel toed boots and hockey shin pads to protect her legs. While incongruous, she could pull the look off and still look hot.

Things really heated up after the weekend when her parents went away for two weeks for a summer vacation. I expected her to throw at least one party, but instead she read books or scrolled a tablet when she wasn't swimming or sunning. Monday afternoon, I looked up from work and drew in my breath. She was tanning face down on the flattened lounge chair, her back naked, no bikini top, her beautiful bum barely concealed by her bikini bottoms, which ventured dangerously close to a thong. I suddenly imagined rubbing sun tan lotion into those pale, firm buttocks, and I surprised myself by popping wood. Maybe I'm 25% hetero after all, but I'm definitely at least 75% gay.

I became suspicious about how much Elliot had told her about our adventures when a splash from the pool caught my attention after sunset while I scrubbed a pot. I looked through the kitchen window over my sink and again caught my breath. She was skinny dipping, swimming laps completely naked, her pale buttocks flexing as she kicked. Wait a minute! Like Elliot when he skinny dipped a few weeks ago, the pool lights and the patio lights were on, the backyard far from dark. When she rose up the ladder, she put me in mind of Botticelli's The Birth of Venus only with shorter hair, a real woman with curves. She looked straight at my kitchen window as she dried her hair, making no attempt to hide her nudity.

What. The. Fuck! Was she testing whether I was truly gay? She strolled lazily through her backyard to the house, casting a second glance at me, only two car lengths from my kitchen window. She even gave an impish wave before she slid open her patio door. I tipped the pot I had been washing the wrong way and sloshed hot water all over my legs and feet.

"Fuck!" I dropped the pot into the sink.

Her motivation puzzled me throughout the next day. Was she an exhibitionist? Did she want to see if she could hold a gay guy's attention, an ego thing? Worse, did she think she could fuck me straight? I've met women who think they can "fix" me, that if I just got properly laid with a woman, I'd stop being gay. That's as bad as a guy who thinks he can fuck a lesbian straight.

I decided to wash the dinner dishes late again, and sure enough I got the same show, her rising out of the pool, her bare breasts firm and dripping, even her pink nipples visible since she'd left on all the back yard lights. My kitchen light over the sink must definitely illuminate me, so she knew I watched. Yet, she strolled naked around the pool, sipping a beer and letting the warm summer air dry her off before she headed into her house.

While watching her, I got hard, which definitely confused me. I put it down to memories of gay sex with her brother, Elliot. Yet she intrigued me. I'd had straight sex before and it was okay, but I way preferred men.

Rain ended her backyard activities until Saturday afternoon when the clouds cleared and the heat dialed up. I took the opportunity to get out and weed my flower garden. I even shucked my shirt, going in just my shorts so that I could get a little sun on my back. While I pulled dandelions from the moist soil, the sliding patio door to her house opened and closed. Because I was on my knees with my back to her yard, I only caught a brief glimpse when I turned my head. Her bikini was so skimpy, her hips and breasts so nice, that again I popped wood, but concentrating on my garden took care of that, and I enjoyed my flowers.

My conscience did nag. I hadn't even introduced myself, which wasn't very neighborly, so when I stood, brushing the soil from my hands, I decided I should say a quick hello. After all, she knew I'd seen her naked. I turned, crossing my lawn toward the little chain link fence, but stopped in shock.

She lay on a lounge chair facing my yard, completely naked except for sunglasses and a black wide-brimmed hat, which was unnecessary since her body was shaded by a big umbrella, a good idea because her pale skin would fry in this sun. Her cute freckles spread from her shoulders down her chest, petering out above her breasts, her nipples pointy and prominent. Her reddish-orange bush stood out, exotic and enticing even though her legs were crossed. She hadn't moved, and with her sun glasses I couldn't tell if her eyes were closed or open. She had to be asleep. Otherwise, she couldn't miss me standing less than ten feet away on the other side of the flimsiest of fences.

I'm not a perv. While I froze for a moment, I decided I should tiptoe away and head back into my own house. I admit that I did linger, drinking in her beauty, just a little longer than necessary. She startled me when she spoke.

"I thought you were gay." She hadn't moved, as if asleep and enjoying the heat of the day. Only her lips moved. Was that the game she was playing, testing my gayness?

"I'm gay. I'm not dead. I can appreciate beauty."

"Like you appreciated my brother's beauty?"

My world shook. I had just assumed that Elliot had kept us on the down low since he was only "25% gay" as he claimed. "Wow! He told you about us?"

"My brother and I tell one another everything. He knew I was gay, like totally lesbian, a couple of years before I came out to my parents. I hear you popped his anal cherry."

Holy crap! They did tell one another everything.

"More like he popped it." Why did I sound defensive? "I was tied to the bed at the time. He impaled his ass on my cock." Yes, I deliberately tried to shock her, but she remained still and serene.

"Yeah, he told me every detail. It really turned me on that you gave up all control, let Elliot do things his way, in his time. Hey, you're not being fair here. I'm completely naked. Drop those shorts and let me see that fat head Elliot so loved."

Telling her to fuck off and heading into my house seemed like a good idea, but it turned me on that it was a command, not a request. My neighbors on the opposite side of my yard and at the back had thick cedar hedges as well as pine board fences. Her neighbor on the far side had a very well maintain cedar hedge too, and everyone on our dead-end street seemed to be away this week, so I decided what the hell. I dropped my shorts and shoved down my boxer briefs, allowing my erection to spring free and stand high. I kicked out of the boxers and walked to with a few feet of the little chain link fence. Since we were playing this game of show and tell, I could stare at her beautiful curves without blushing.

"Nice cock." She still hadn't moved, and if she weren't speaking, I'd think she was asleep.

"I thought you were a lesbian," I said.

"Oh, I am. Totally into girls, not guys, but like you said, I can admire beauty. You're in super good shape for thirty-one. Elliot says you're a runner and a swimmer, and it shows. Besides, I'm not into hairy men, and I love that you have a smooth chest."

"Thanks." My cheeks warmed. Was I blushing? I am pretty proud of my flat stomach, my abs, my lightly muscled shoulders. I'm too old to be considered a twink since I'm over thirty, but my efforts have certainly kept the twinkie aspects of my body firm. For a moment neither of us spoke, and it turned me on that we shamelessly drank in each other's naked forms in broad daylight. It was so naughty.

Finally, she sat up and took off her sun glasses so that I could see her brown eyes. "Jamie, right? I'm Madison, Elliot's older sister. He tells me you have quite the dungeon in your basement."

Again, my cheeks warmed. "Wow, You and Elliot are super close."

She stood, dropping her sunglasses onto her lounge along with her wide brimmed hat, and picked up a small pack from because the chair, slinging it over her right shoulder.

"I want to see it," she said. Without waiting for an invitation, she walked up to where the fence ended at the back of her house, opening the little gate that gave access to the strip of grass between our houses. She opened my complementary gate and let herself into my back yard.

Was my jaw hanging down? Anyone walking or driving by on the street who happened to look between our houses would have gotten quite an eyeful of her naked body. Daring!

"Come on, gay boy. Show me this dungeon." She put her hands on her hips, her feet slightly apart, like a military commander giving an order. It was so incongruous, this naked freckled woman, her breasts thrust shamelessly forward. She smirked at my discomfort.

"Okay, why not? Since you know all about it." I tried to sound casual, but my heart rate definitely picked up. I was a gay naked man with a solid erection, leading a naked lesbian into my basement dungeon. What did she have in mind? A dozen scenarios flashed: me in the pillory, my butt red from the flogger, her tied with her hands above her head, her bum and breasts red from my attention. I really didn't know what I wanted to happen, but I wanted something to happen.

I led the way downstairs, flipping on the pot-lights, turning and stepping aside to wave her into the dungeon. She stopped and whistled, giving me a sly glance before she continued deeper to inspect my half-finished basement full of toys.

"Elliot's right. You are a kinky fuck."

She headed for the pillory first, checking out the holes for the head and wrists. "Like the puritan punishment only for fucking. You ever fuck anyone who you've put in this contraption?"

If I wasn't already hard, I would've popped wood just from the memory. "Elliot fucked me when I was stuck in that, and he's not the first, but it was his first time fucking a guy."

She looked up at one of the many full height mirrors that I had strategically placed around the basement. "Did you watch him fuck you with that?" She pointed to the mirror.

"Yup. He's fucking beautiful and watching him fuck me was like watching porn and feeling it at the same time. Call it an immersive experience." Now it was my turn to smile slyly.

She checked out the manacles hanging from the unfinished ceiling, reaching high to grab them and hang on as if she were secured standing, making her small breasts rise. "I like these," she said. "I see that mirror is perfect for the sub to watch themselves get flogged."

Should I offer to restrain her? My gut said she was a top by the way she ordered me around. Should I ask her to restrain me? I was up for any game right now. This was so far outside my expectations or fantasies that it was new and exhilarating. Before I could suggest either, she headed for the X.

"Now this really interests me." She stopped spread her arms and legs, assuming the position of being tied to the X, pushing her pale buttocks back at me. "This way?" she said before turning stand as if tied to the X facing out, her breasts and pussy so vulnerable. "Or this way? Which way do you use it, gay boy?"

"Both." My mouth went dry. "But if you want to fuck a guy, usually face forward."

"Like what you see?" She stayed in the X position as if tied there. I hadn't licked pussy in over a decade, but suddenly I wanted to get on my knees and give it a shot.

"Yes. You're stunningly hot."

"I wasn't when I first got to college. I was pretty hefty, and guys just ignored me. It was like I was invisible. They were assholes to me."

"Sorry to hear, but you lost a lot of weight. How'd you do it? Drugs?"

"Nope. Old fashioned running and swimming like you, and diet, but guys taunted me for even trying. I'd be jiggling my way down the street, fighting to lose weight and look good for them, and like, more than once guys shouted 'Run, fat girl, run,' from are car as they passed. Total dicks!"

"Bet they changed their tune later."

She shook her head and pulled on the ropes. "It took a couple of years, but yeah, some drooled over me, but some were still such pigs. I was running along a trail once, and a guy running the other way turned around and ran along side. I was actually interested cause he was hot. You know what that fucker did? Instead of asking me my name, he asked if I'd suck his cock. Just like that. No pick-up line, nothing. That's the sort of question you ask a whore, and I bet that dick has used women that way, just holes."

"I apologize on behalf of all men. Just so you know, I've had gay guys walk up to me at clubs and ask the same question."

"Fuck you, it's not the same." She let go of the restraints and walked close to me, reaching forward. She grabbed my cock and squeezed, forcing a shudder through my whole body. I could've slapped her hand away, but I just stood there transfixed.

"You go into a club," she said. "You're looking to get laid. You're running down a trail, you're looking for exercise. It's not the same." She gave my head a vicious squeeze, but I didn't pull away. I just stood there, meeting her eyes, taking the pain. "Tough guy." She relaxed her grip but she didn't let go of my cock.

We stood frozen, our eyes locked together, challenging. I could've reached forward and grabbed her pussy, but I sensed that she was in charge, so I waited to discover what she craved. I resisted the urge to start thrusting against her grip on my erection.

"I have a proposition for you," she finally said. "You say you apologize on behalf of all men? I want to punish you on behalf of all women. I want you to be my whipping boy. How do you feel about that?"

Goosebumps sprung up all over my body. My anus clenched. While I'd dabbled in spanking and flogging, I sensed that this would push me beyond limits I'd never crossed. I was terrified and aroused. Could I take what she dished out? My mouth went dry.

"No permanent marks," I whispered.

Madison let out a sigh of relief. "Awesome." She gave my erection another shudder-inducing squeeze. "No here's my super kink. Your safe words are yellow light if you want me to tone it down, and red light if you want me to untie you. Otherwise, I want you to play at being the unwilling asshole who I got the better of and tied up. No means yes. Are you good with that?"

"Yup." I tried to sound confidant, but I was deliciously afraid.

She let go of my cock and pointed to the X. "Assume the position, bitch!"

Wow! Her authority, her tone, prompted me to hurry to the wooden X, spreading my legs and arms, my ass feeling so vulnerable. She didn't waste any time, securing my wrists and ankles in the leather cuffs. Chains secured them to hooks, and by going up on the links she stretched my arms taunt and my legs wide.

I checked out the full-length mirror I had set up so that the sub on the X could see himself profile. She stepped back to admire her handy work, her hands on her naked hips, her tits thrust out proudly.

How can I make this better for her? Play into her fantasy. I strained and thrashed for a second at my restraints, making the chains clap against the wood of the X. "What the hell?" I called out. "Let me go, you crazy bitch!"

Her mouth opened a bit as she let out a sigh. "Oh, this is gonna be awesome." She glided up so that her lips were just an inch from my left ear. "I'm going to make you squeal, pig."

Smack! The slap shouldn't have caught me off guard since I could see her hand swinging down, but it was like it was happening to someone else until the impact. It hurt! I thrust my buttocks back but remembered to stay in character.

"Fuck off! That hurt!"

She looked up at the mirror so that she could see both of us. She raised her hand and held it ready. "What, this bitch?" She swung her hand down and another serious smack hit my right buttock.

How to give her permission to really get into it? Taunt her. Make her angry at all men.

"Suck my cock, you slut."

Her eyes went wide, and her mouth opened in surprise. "Why you fucking dick!"

The spanking came fast and furious, alternating between buttocks, the pain increasing with each slap. I shoved back in challenge but my heart pounded in fear. I had unleased an angry monster. Watching her efforts in the mirror, her breasts bouncing with each slap, provided distraction for the pain at first, but she took me to a new level, and cries were forced from my lips with each smack despite my efforts to be stoic.

"Ow! Fuck!, Oh Fuck! Stop it!"

That really turned her on, and the slapping only became more frantic, sweat now glistening on her freckled skin. Finally, just when I thought I couldn't take more, she stopped to catch her breath. She stood behind me like a man getting ready to fuck my ass, and grabbed my buttocks.

"Oh my god!" I gasped as she massaged in the pain. "Fuck that's intense."

Her lips caressed my ear and her sharp nipples pressed into my back. "Such a nice shade of red," she whispered. "I think I want to see your skin red all over."

She pulled away and moved about the room, glancing at herself in mirrors as she searched for tools. She noticed my chair in the back corner and pulled it out under the light of one of the pot lights. It was a normal wooden chair, but wrist restraints had been installed behind the back and ankle restraints on the bottom of the legs. A dick-sized vibrator, complete with plastic testicles, stuck up from the seat. The only way you could sit in that chair was with the vibrator up your ass. I sometimes used it when I was alone and horny, fucking myself, leaving one hand free for masturbating.

"This could come in handy, but not yet." She turned away to the tool bench, and whistled at the line-up of vibrators and dildos of various sizes, the boxes of condoms and bottles of lube. The cat-o-nine-tails and the riding crop really galvanized her attention. She picked up the cat and struck it against her thigh.

I remember my role play. "No, not that. Please!" Of course, what I meant was please flog me! I was scared yes, the skin on my back, butt and legs tingling with anticipation. This was going to hurt and I wanted it too. I wanted to be tested. For emphasis, I struggle at my bonds, making the chains clap against the wood of the X, proving I was totally helpless.

She looked to me and gave that sly smile. "This is going to be good. Finally, a man gets what all men deserve."

"Fuck no! Stay away from me with that!"

She did what we both wanted. She crossed the space between us in three steps, raising the cat as she moved. I turned to watch in the mirror. She hurried with her arm high, her breasts jiggling with her motion, an avenging angel. I could see the moment of contact but the feeling slashed into my shoulder blade.

A screamed ripped from me and I panted, absorbing the pain. I'd had this cat used on me before but not with this vicious ferocity. It wasn't as dangerous as it looked because the nine tails were soft cloth, not harsh rope like a 19th century navy would've used. It took serious effort to make it hurt.

She swirled it in the air, teasing me with anticipation before suddenly striking my other shoulder blade. I lunged against the X, my hard-on below the wood center of the X and thrusting at air. Oh, I begged for that to be touched.

My head sagged forward as a series of slaps hit my back, my sore butt, the back of my legs. It's a good thing her parents were away and we were in the basement, or the police might've been called because of my repeated screams and curses. I closed my eyes and let each painful blow wash over me. Finally, I hit a wall, gasping in the pain, absorbing it, fearing I couldn't take more and I'd be humiliated into using the safe words. It was a contest of wills. Did she want to drive me to use them?

The flogging stopped, and I hung from my wrist cuffs like a rag doll, my legs giving out as I gasped for breath. Her lips kissed my neck, and I knew what was coming next. She grabbed my buttocks and squeezed.

"OH GOD!" I screamed as the pain sank deep. "Oh god! Oh god! Oh fuck me!"

"That will come in time." Her lips teased my earlobe, biting and tugging. "Look in the mirror."

I turned my head. She stepped back and turned so that I could see her full frontal, her chest heaving as she caught her breath. She held the cat with the slim handle between her breasts. With her free hand, she pinched each nipple in turn, groaning with pleasure.

"I have never been so wet," she said, the cat handle descending, now over her stomach, passing her belly button, sinking into her orange bush. She spread her legs shoulder width apart and looked up at me in the mirror. "I bet you wish you could go where this is going, you fucker."

Slowly, she pushed it up into herself. "Oh fuck yes." She gave a groan of pleasure, shoving the narrow handle deep, her free hand rubbing circles on her clit. She was right. This gay guy wanted to fucked her desperately. I'd been hard and untouched for half an hour while every nerve ending in my body had fired many times. I leaked copious pre-cum.

"Oh so much better than a man." She thrust the handle in and out. She met my eyes in the mirror. "I can rely on this to stay hard and not come before me. So much better. My pleasure." She pulled it down and out. "And your pain." She savagely whipped my buttocks.

The pain seared. "Bitch!" I screamed. How much more could I take? I hit subspace, just hanging there, letting the pain wash over and through me. I loved being helpless against her fury, absorbing the punishment that all those frat boys deserved. The Whipping Boy, being punished for other men's sins.

She shuddered, her chest flush with her passion, the cat in her hands and ready. Would she hit me again or would she ride the handle? I've never been more alive. She dropped the cat.

"I need to fuck you," she said.

She picked up her pack and pulled something out, a dildo but tangled with straps. A strap on! But not just any strap on. She held it near my head and grabbed my hair to turn me to see it close up.

"See this," she said, pointing to a thin, short vibrator in the panties of the strap on. "It actually fucks me." She turned it on and the little cock, no more than three inches long, pushed out and in while vibrating. "That's for me. This is for you." It was a cock-sized vibrator, at least six inches long, complete with balls, sticking out the front. "And the best part, every time I get all the way into you, I'll feel the base vibrating against my clit. That's right, the deeper I fuck you, the more I get pleasure. I'll fuck you to my orgasm, bitch boy."

This was fantastic, but I remembered my role: all those frat guys would freak.

"No!" I said, meaning yes. "Please don't fuck me!"

She put down the strap on and went to the bench, turning with the riding crop in hand. It whistled through the air and slapped her palm. "You will beg me to fuck you."

This would be way more painful than the soft cloth of the cat. I bit my lip and knew fear. I wanted to be fucked, but I wanted to put up a fight too. She rushed me, and the first blow on my lower back caused me to thrust forward and scream.

"Oh my fucking god!"

"Beg me!"

It was a test of wills. The crop was leaving welts on my back that would take days to heal, I could tell. I bit my lip and hung on. The air whistled and my shoulder blades seared with pain. She worked down, prompting screams and shouts, but I could tell she was impatient, wanted to break me quickly. When the crop hit my very sore buttocks that was it. On the third blow I caved.

"I give in!" I shouted. "You win. Fuck me. Please stop and fuck me."

She dropped the riding crop. "Since you ask so nicely." She went to my tool bench and got a condom and rolled it over the vibrator, lubing it up generously.

She stepped into her strap on, and her body shuddered and she looked to the ceiling as she inserted the little vibrator into her vagina and turned it on. I could hear muffled vibrating as it thrust in and out.

"Oh fuck, yeah," she gasped. She pointed the cock at me and stepped between my legs. She licked the back of my ear. "Here it comes, you slutty bitch."

She pushed hard with no warning. My anus widened reluctantly, painfully, but she was merciless. The head forced passed my anus, popping deep.

"Oh fuck, that's big."

"Take it you faggot frat boy." She thrust far into me.

It hurt to go so deep with no attempt to widen my rectum gently. Is this what a virgin felt when an inexperienced frat boy shoved deep? I bent my head and focused on relaxing, welcoming the vibrating cock. She shoved it all the way into my ass.

"Balls deep," she said. "That feels so good."

"It hurts," I gasped, remembering my role play.

"So what," she said. "It feels good to me."

She pulled almost all the way out and thrust back in. She crushed close to me, her hips pressing against my tender buttocks sending stabs of pain, her sharp nipples against my sore back. I looked to the mirror and saw a broken man hanging from his cuffs being taken by a beautiful woman, thrusting repeatedly into him. I was so turned on!

"Oh fuck, oh fuck!" she gasped, thrusting faster and holding deeper to get the most of the vibration against her clit. Her hands gripped my hips to aid her thrusts. She became frenzied, and I hung on for dear life, my prostate crushed and pushing me toward a hands-free orgasm.

"Ugh!" I grunted like an animal as a weak spurt of sperm oozed out of my cock, not a real orgasm, frustrating as hell. Another followed but it provided no relief. I needed to shoot!

Suddenly she held tight as deep into me as she could get, her head thrown back, her mouth open. "Fuck yeah!" She screamed, gyrating and twisting her hips, yanking the cock in my ass left and right as she shuddered with her orgasm.

She held deep, but the vibrating on her clit must've been too much because she pulled out, and undid the strap on, turning it off and letting it fall to the floor, but she stayed with her hips pressing against my buttocks, her breasts press against my back, her breath on my neck, the scent of our sweat, my sperm and her juices all mixing into a heady aroma. Her body massaged in my pain.

"Did you come?" she asked after she caught her breath.

"Not really. It was close."

"Well now you know what it feels like, frat boy."

She undid my right wrist and my right leg and turned me to face her, my left wrist and leg still attached to the X. "Finish yourself, frat boy, just like a woman would have to after you roll over, fart, and go to sleep."

"With pleasure," I said, forgetting the role play. I grabbed my cock and it spiked with pleasure, so sensitive because it had been denied attention while every other nerve-ending had fired. I wouldn't need to stroke long to bust this nut. As it built, I suddenly realized I had to give fair warning. She stood only a foot in front of me, looking into my eyes to watch my reaction.

"You should step aside."

"What?" Her eyes went wide but she complied just on time, turning sideways so as not to be in the line of fire.

The orgasm exploded from my body, the first shot going three feet, the second two feet. I lost count, pulsing and pulsing, squeezing out every last bit of the ejaculate. Was there any fluid left in my body? I sagged against my wrist cuff. Surely I was nothing but a dried out husk after shooting so much sperm.

"Holy fuck, dude!" She stared at the splatter on the concrete floor with eyebrows raised. "I thought guys only came like a teaspoon of sperm. What the fuck? How could any condom hold all that?"

"No," I gasped for breath, sweating and trembling. "It usually is just like a teaspoon, but if you keep a guy hard and teased long enough, especially a young guy in his early twenties, then yeah it can be spectacular like this, but it's rare. You've never been so wet? I've never been so hard and dripping and desperate to orgasm."

My breathing slowed, but she still stared in fascination. "You're still hard as a rock." She grabbed my dick to test its firmness, forcing a full body shudder from the pleasure, almost pain since it was so sensitive.

"That was my super power back in my first year of college when I still dated women. I'd come pretty easy, but I'd stay hard, put on a fresh condom and go for round two until they came. Sometimes I came twice, joining them in their orgasm."

She turned away and walked over to the dildo chair to stare down at it. She turned back to me, biting her lip. "Okay, I never thought I'd do this, but I want to lose my virginity to a real cock. Don't get me wrong, I'm still a totally gay, but when women talk about sex, I want to know what it's like. Don't think this'll ever happen again."

"After that orgasm, whatever you want." My legs trembled with the excitement, all my nerve endings on edge from the whipping. I'd had fantasies about a guy getting this rough with me, but my partners have always been gentle and timid in the spankings and whippings, fearing to take it too far. She had no fear.

She undid my wrist and leg strap and guided me to the chair.

"Here's how I want to lose my virginity," she said. "You have to sit in the chair and get fucked by this." She flipped the end of the dildo to make it wave back and forth. "And I'll lower myself onto this when I'm ready, at my pace." She grabbed my erection, forcing another shudder. "Like Elliot, I want complete control of my first time."

"Whatever you want." My senses of pain and pleasure were completely jumbled. Goosebumps broke out all over my body.

"Sit." Her command was not in dispute.

I got a condom and a bottle of lube from the tool bench and sheathed the dildo, lubed it up and turned it on, the buzzing obscene. My anus was already very lubed from the fucking, so when I lowered myself, it slid in easily, but as I bottomed out sharp pain from my buttocks and the back of my legs from the whipping forced a cry from my lips. "Oh fuck!" Sitting would be a challenge over the next few days even without a vibrator up my ass. The pleasure of the vibrator mixed the pain from my whipping into a wild sensation, every synapse in my body firing. Even though it was a small vibrator, sitting on it filled me as if it were a huge cock, and the vibrations ground into my ass and prostate, coming straight up from the plastic balls and shaft.

She quickly cuffed my wrists behind the back of the chair and my ankles to the legs. Pleasure coursed from my cock as she rolled on the condom and caressed it with lube. She carefully stepped over the chair so that she could sit on my lap. She slid forward until her bush pressed against my penis, sending spikes of anticipation.

When her lips inches from mine, teasing, she whispered, "I've had lots of dildoes inside me, but this is the first time it'll be a live, warm cock that doesn't vibrate. I'm very curious as to whether it can live up to my girlfriend's strap on."

She raised herself up until her vulva caressed my fat head, mixing her juices with the lube, sending pulses of pleasure down my shaft. Finally, she used a hand to aim it. She slowly settled.

She gasped as gravity brought her down, forcing my head into her very tight vagina. "Oh fuck," she whispered, her eyes glazing, unfocused, her head thrown back as she concentrated on the sensation in her canal. "That's big."

"Fuck you're tight." I hadn't expected such compression. It was as tight as any man's ass that I'd penetrated.

Deep breaths came from both of us as she relaxed her legs, forcing my cock deeper and deeper into her until she bottomed out, which sent thrills of pleasure through me because now the weight of two humans pressed the fake balls and the vibrator against my anus.

I could see in the mirror that her feet were on the floor, so she was able to push back up, almost rising off my cock, but when my head neared slipping out, she relaxed and this time slide down with a rush on my pole.

"Holy fuck," she gasped.

"Oh my god! Fuck me."

While meant as an expletive, Madison took it as encouragement and rose up again, and I rose up with her, shoving up with my hips despite the pain from my shoulder blades on the back of the chair from the whipping. I almost got off the vibrator before she relaxed her legs, sliding back down on my cock and forcing me roughly down on the fake cock, the sudden penetration for both of us exquisite, and for me, a mixture of pain and pleasure as my whipped buttocks hit the seat.

We got in a total fucking rhythm. Her rising almost off me, me rising almost off the vibrator, before she'd let gravity pull her down, forcing my cock into her and my vibrator into me. We grunted and groaned like animals rutting. Her boobs bounced up and down right in front of my face, so I decided to take action and managed to catch her left nipple and suck it hard into my mouth.

"Oh, fucking yes!" she shouted, riding me ruthlessly now, her hand grabbing a fistful of my hair at the back of my so that she could hold my lips tight to her breast. The scent of her, of my sweat and hers, of the lube and sun block, her subtle perfume--all mixed into a heady aroma that only turned me on more. This was primal, urgent sex.

I held out far longer than I normally would've under such a ruthless assault on my cock, but only because I'd already had one climax. Yet, I could feel a second orgasm rising up in my loins, unstoppable at this pace.

I threw my head back, my unfocused eyes going to the ceiling. "Oh, fuck. I'm going to shoot!"

"Not yet!" she shouted, riding me faster and more desperately. She grabbed my right nipple and twisted savagely, causing shooting pain. It distracted me enough off the pleasure in my shaft to give me a second to reset, the ejaculation postponed.

She changed her technique, forcing me down and grinding her pelvis against mine as she rubbed her clit with one hand. She grabbed my hair again and pulled me onto her right nipple, which I sucked in roughly and eagerly. That put her over the top.

"Oh my fucking GOD!" she screamed, holding herself tight against me, my cock buried as deep as possible inside her.

Her vagina spasmed, squeezing in pulses against my hardness. I didn't even know that was possible! I exploded immediately.

"Oh fuck! I'm coming so fucking hard!" I shouted, tossing my head back, letting my brain focus on nothing but the shooting pleasure of my throbbing cock.

She rose up one last time, and I thrust up with my hips, desperate to stay inside her squeezing pussy. I rose too high and the vibrator popped out of my ass, and when she relaxed her weight, again forcing me deep, fake cock slid up my crack toward my spine, vibrating obscenely loudly now that it was outside my body, my butt cheeks coming to rest on the edge of the chair.

We both froze, drinking in the pleasure, our breathing slowing. She grabbed my head and pulled my lips to hers, and we kissed with passion, our tongues exploring. Finally. she broke off and met my eyes with her deep brown eyes.

"That was awesome," she said. "But I'm still gay, like a total lesbian."

"Yeah, I'm like 75% gay. I'll never be straight, even with sex as good as that."

"Me neither." She kissed me again. "I like that, Elliot's thing, right? It's a spectrum. I guess I'm 75% lesbian, but I'll make time for a kinky twink like you, and I'm going to be here all summer."

I gave her a quick kiss. "My dungeon is your dungeon."

It was going to be a kinky, sex filled July after all. Summer just got way better.

Note to fans. This is the sequel to my Literotica Story, The Seduction of Me. I didn't put it in the gay category because it's between a man and a woman, and it's heavy BDSM. Thanks for your feedback and comments!