[The story won’t make sense if you haven’t read part 1. Part 3, if it comes, will complete the story.]
“What’s bothering you?” Julie asked.
She said this to the back of my head as she followed me out of the meeting room. “That was an important design meeting, and you were somewhere else? Care to tell me where?”
I don’t think so, I said to myself as I looked at my watch. It was Friday and I was trying to leave early. I had to get home and clean up before heading over to Mona’s where, I could only imagine . . . well, I’d been trying to imagine it for two days and now I didn’t want to think about it anymore.
“Hey, wait a second, will you,” Julie said. “Just wait a second.”
“Can’t Jules,” I said. “I gotta go.”
“What the hell is going on? Are you okay?”
“I’m fine,” I said. “Just leave me alone, please.”
“Won’t you just talk to me for a minute? I was hoping we could go out to dinner tonight.”
Now! You fucking say that now? Today? Jesus Christ. “I can’t Jules, I can’t. I’ll call you.”
If she’d only asked a week ago. It could have been a different world.
✤
Julie and I worked on the same project team building a new 1.0 business intelligence software product. I was the marketing lead and she was the engineering manager. It was my job to come up with the list of features for the product, and her job to manage the engineers who designed and built them. A lot of the male engineers didn’t like working for a woman, but Julie was a lot smarter than they were and they knew it. So despite their resentment they busted ass to impress her.
Of course, it helped that she was gorgeous as well as brilliant. With her blonde hair, upturned nose, full lips, and a smattering of freckles, she nailed the girl-next-door archetype. And it all went with a body that’s hotter and curvier than you’d expect from the girl next door, so I guess she’d even improved that ideal. I had a major crush on her from the first moment we met, but it didn’t take me long to realize she was out of my league. Yes she was hot. She was also tough and smart. What more could a guy want?
Not that it mattered, though, because she was living with Doug, our QA manager. They were a cute couple with an odd Mutt-and-Jeff touch. Doug was a former college linebacker; at six feet four inches and too many muscles he towered above Julie who barely cracked five three. Doug struck some people as trying a little too hard to maintain his macho, college-boy bona fides. Most of us thought Julie was the one in the family with the brains. Some of us also thought she was the one with the balls.
With my crush destined to be just another candidate for my closet of broken dreams, I settled for friendship. Julie and I scheduled lunch every Monday to review project status. That went to two and later three lunches a week as the project developed, problems arose and deadlines came closer. Our relationship grew as well. It didn’t take long to realize that we shared the same interests in restaurants, modern literature and very old music. (It’s not easy to find someone who loves sopranos singing Handel arias.) Soon we were talking about almost everything except work. And the conversations started getting a little personal. I’ve always been closer to women than to men so it was easy for me to open up to Julie. It was more difficult for her but she was getting there.
But we weren’t BFFs and, much as I would have preferred otherwise, it was still basically a work relationship. I didn’t try to change that. Doug wasn’t my favorite person, and, to be truthful, they moved in a more hip circle than I did.
A few months back Julie asked if we could go to lunch off campus. We drove to a small Indian restaurant she liked across town and settled into a corner booth. We ate slowly, tossed around some pleasantries but made no attempt at serious conversation. Well, I ate; Julie mainly moved her food around as if the plate was a canvas and she was creating a gustatory abstract. If there was something bothering her, I’d let her get to it in her own time.
When the table had been cleared she looked up at me with an expression that was barely holding sadness at bay. Her eyes had faded from their usual bright blue to a pale gray and her lips were trembling ever so slightly; you had to look closely to see it. I’d never seen her look like that. She said, “I need to ask you something.”
“Sure,” I said. “Anything.”
“This is hard,” she said.
“Take your time.”
“Okay.” She folder her napkin into a square and brushed some invisible crumbs away. She said, “After Doug went to bed last night I used his laptop to download a file from the office I wanted to review. I’d left my laptop with IT for a memory upgrade.” She stopped to pour herself some tea but didn’t drink it. “Anyway, I opened a folder and found tons of bondage photos. Women tied up with rope and leather, bound and gagged in the most grotesque positions. It was really hardcore shit.” She cast a glance toward the door.
“Why would he have those? He obviously downloaded them. Is that what he wants?”
How the hell was I supposed to respond to that? “I wouldn’t make too much of it,” I said. “Men like to look at pictures of naked women.”
“These were more than just naked women. They were scary. I don’t understand. We’re doing good. He has everything he could want. The sex is great, even a little kinky.”
I didn’t need to know that.
“Should I say something to him? Do you think I should say something? I’m going to say something.”
I’d never seen Julie like this, shaken and confused. She was always in control. Even in her happiest, unguarded moments, her eyes always told you she was on top of everything.
“Just don’t do anything rash. I’m sure it’s nothing.”
But she did confront him. She was in my office at 8:30 the next morning. Doug had dismissed her questions. The pictures meant nothing. They were a joke. His old college roommate sent them; everyone knew he was a boor. At 32 he’d already been divorced three times. Doug deleted the pictures then and there. Everything was cool, she said.
Less than a week later Julie got home from work and found that all of Doug’s stuff had been moved out of the condo and, apparently, Doug along with it. She got an email from him around midnight saying it was over. He said he was sorry but their relationship just wasn’t working for him. He’d met someone else and was moving in with her.
He didn’t come into work for the rest of the week and wouldn’t respond to her phone calls or emails. And then we heard that he was taking three week’s vacation. It was short notice, but the project was still in the early design stage and QA activity was slow.
Julie was shaken but managed to be stoical at work. She was too strong and determined to let it affect her job. She had nevertheless been thrown off her game and was pissed that Doug had refused to talk to her. She was an engineer; she wanted to know why something didn’t work, what was broken. If there’s a problem you fix it. If you can’t fix it, move on.
We talked a lot over the next few weeks. Our lunches continued but we also met frequently in her office, checking in, taking a pulse. We even went out for a drink after work a couple of times; the first time we ever spent together outside of work.
Doug came back and dropped two more stink bombs out of the blue. He quit our group and took another manager position in a different division. Julie and I both figured he must have interviewed for that slot a while back since he’d been out of town the last three weeks, which meant he’d been planning this for some time.
Even more of a shocker was that he was married. The mystery lady he’d left Julie for was his new boss’s secretary; excuse me, executive assistant. Janice was a sweet girl and the opposite of Julie in every way. She was a sweet girl but a bit of an airhead. Perpetually bright-eyed and cheerful, she was always willing to talk about the latest episode of American Idol. Her major skill was being able to type 125 words a minute on any keyboard you threw in front of her. Okay, we were snobby, but she wasn’t the sharpest pencil in the drawer. On her first day back in the office she handed in her resignation. She told everybody that Doug didn’t want her to work; she was going to stay home and take care of her man.
Well that knocked any residual sadness and self-doubt out of Julie. Obviously she had just been too much for Doug, too smart, too strong. “What I really don’t understand,” she said, “was why I didn’t see what an asshole he was.” I didn’t tell her that everybody else had seen it. People see what they want to see and so often that means that they blind themselves to the obvious.
Julie was her old self again. In fact, she was better than ever since she was free of Doug. She was smiling and joking and she was driving the engineering team with an overdose of good cheer and optimism.
I marveled at her. Hell, I fell in love with her all over again. At her lowest moment she’d come to me for friendship and reassurance. Was there a chance for me? Could I even think of aiming so high? I decided not to push it. I’d bide my time and wait for her to come to me. I wondered if men ever got the women they deserved.
And then today of all fucking days Julie asks me out. Of all goddamn fucking days. Why didn’t she ask last week? No, she asks on the night I’m going over to the house of a woman I just met who is going to strip me naked and offer my holes to her friends as a party favor. . . and I’m going along with it.
“I can’t Julie, I’m busy. Sorry, I gotta run.” I just left her standing there.
Halfway down the block, I wanted to turn and see if Julie was still standing there watching me, but I didn’t.
✤
I spent the short drive to Mona’s looking around and reading store names out loud in a lilting singsong, just like my father used to do. I gripped the steering wheel hard to try to stop my hands from shaking. I was actually physically weak. My thoughts were dancing around in my head, lighting briefly on my most painful memories, those moments when I felt scared or timid, moments that embarrassed me to think about. But a memory left as quickly as it came, only to be replaced with another and then still another until all I felt was one big ball of despair drawn from a lifetime’s desperate moments.
I parked around the corner from Mona’s. Without looking where I was going I walked mechanically to her building and up the stairs to the front door. I ignored the doorbell and tapped lightly on the etched glass door panel. As I waited I looked around behind me, half expecting people to be staring at me.
Mona opened the door. “Good,” she said. “I knew you’d come.” I walked in and she closed the door behind me. She stood there and looked me up and down. After a few seconds she shook her head almost imperceptibly and curled her lips in irritation. “Well,” she said, “you know what to do.” I began to undress, folding my clothes neatly and putting them in the covered wicker basket next to the door.
I stood there as naked as I’ve ever been in my life. Instinctively I covered my cock and balls with both hands.
“Tsk, tsk,” Mona said and cast a glance up at the ceiling.
I removed my hands. “Okay,” Mona said. “Follow me. I’ll show you around.”
Just then Carole walked by carrying a couple of shoeboxes. “Hi, Ishy. Good to see you,” she said, and laughed as she kept going.
Mona took me on a quick tour. There were three bedrooms, an office and a bathroom off the hallway to the right. The main area was a living room, which I remembered well, that turned into a dining room at the far end. A door on the left led to a large kitchen that had been completely remodeled with all the latest high-end appliances. There was a door that led out to a small but beautifully manicured back yard.
I was only half paying attention as we moved through the apartment. I didn’t give a damn about the House Hunters walk through. I was naked in a house with two women I barely knew. They had sexually used me, doing things to me, no . . . making me do things to myself that I could never have imagined doing in front of others. And I had come back for more. What the fuck was I doing?
As we went back into the living room I noticed a table behind the couch that I hadn’t seen before. It was a narrow glass table that ran the length of the back of the couch and was almost as tall as the couch itself. Mona saw that I was looking and paused so I could take it all in.
The table was covered from end to end with a delicate lace runner. Laid out neatly on the runner were a variety of bottles and plastic squeeze jars of lube. Next to them were about 20 or so vibrators of different shapes and sizes, some with cords and remote controls. Then came a line of dildos in different lengths, girths and colors. Some of the dildos had larger flat wafers at the base. I guessed they were designed to fit into the strap-on harnesses piled next to them. I felt a knot burst to life in my stomach. Mona nudged me forward. “Come on,” she said.
Mona sat on the couch and motioned for me to stand in front of her. Carole, who I now decided was younger than I had at first thought, twenty-five at the most, came into the room and sat down beside Mona. She was strikingly beautiful, with long dark hair, perfect almost pure white skin and garish red lipstick. She was wearing a loose, low-cut, sheer black sleeveless blouse and a floor-length wraparound skirt tied closed on the side of her waist. She pulled her legs up and tucked them under her. I was beginning to recognize that as her usual position.
“Let’s have a look at you, Ishy,” Mona said. “You are clean, right?”
I nodded.
“Show me,” she said.
I didn’t understand. I guess my expression gave that away. “Oh, come on,” she said, the exasperation evident in her voice. “Turn around, bend over, and spread your ass.”
As many times as I’ve heard that from her already, it still startled me when she said it. What startled me even more was that once again I said nothing and did it.
I felt her finger draw a light circle around my anus. “Okay. Good. You can stand up and turn around.”
Carole leaned back and picked up a dildo from the table behind the couch. She bent forward and pushed my cock to one side and then to the other with the dildo, like TV detectives do with a pen when looking for evidence at a murder scene.
“He really should be shaved,” she said. “Think how much cuter he’d be with baby-soft skin rather than that thick stringy mess. Ugh. Yuk.”
“You’re right,” Mona said, but it’s too late tonight. Maybe tomorrow. I bet you’d be happy to take care of it?”
“Oh, yeah,” Carole said, and that big bright smile made another appearance.
“Let’s talk about tonight, Ishy” Mona said. “Some special ladies will be coming over. They’re a really fun group actually. Once the party gets going and everyone has loosened up, we’ll bring you out. You got a look at the table over there. I think that gives you a pretty good idea of what to expect.
“I’ll bring you into the room so everyone can get a good look. And then you’ll get into your down position and wait for someone to come get you and start the ball rolling.”
“You don’t mean you want me kneeling and, you know, using my hands to . . . uh, spread . . .. You can’t mean that. That’s too much. I can’t, I just can’t.” I started to whimper.
“You can and you will,” Mona said.
“They’re going to have fun with you, Ishy,” Carole chimed in.
Mona shot Carole a shut-the-fuck-up look and then turned back to me. “Most of them will just want you to eat them out. You might find yourself in front of the couch, moving down the line, doing one after the other.
“Of course, a few of them are going to want more,” Mona said. I looked over at Carole. She’d taken a strap-on harness off the table and was twirling it in the air around her index finger. Mona took it away from her. “The important thing, Ishy, is that you do your best to please them. You’re just a nameless little boy to them that they’re using for their own pleasure; that’s all you’re good for to them. They’re not going to be thinking about you, about who you are. They certainly won’t recognize the embarrassment that will be consuming you, that overpowering feeling screaming at you to get up and run, and the naked need that stops you from doing it.
“But we’ll be watching that. We won’t miss a juicy exquisite moment of it.” Mona looked at Carole who was still beaming; she was fondling a bright red dildo. “Well I won’t. I fear Carole’s going to be in the party mood with our guests.”
I wiped my eyes and sniffled. Were they really going to expose me like that? Was I going to let them? How could I? And then I felt some movement in my crotch. My cock was actually getting hard. I held my face in my hands. Did I really want this? Did I need it, like Mona said?
I looked over at the two women. They were chatting, heads together. They were having a good time.
Mona turned to me. “There are a few things to remember, Ishy. Don’t talk to anyone. The guests know not to engage you in conversation. They may position you or tell you what they want, but that’s all. Second, don’t resist. Do what you’re told. You’ll be completely safe; nobody’s going to hurt you. There’s no hitting, slapping or corporal correction allowed; no foot worship or other silly “internet dom” stuff.”
“Spanking is okay, though, right?” Carole said. “And whatever you do, Ishy, don’t come. That’s for the grand finale.”
“The what?” I said, but no sound came out. “Doesn’t it ever end?” My lips barely moved.
Mona jumped in, “If you come, Ishy, you come, but I don’t think you will. You’re going to experience a lot of things tonight, but I doubt arousal will be one of them.”
There was no mirror but I was sure my face was totally drained of color. My expression must have told Mona that I was close to panic.
Mona stood up and put her arm around my shoulder. “It will be okay, Ishy. You’re going to get through it and when it’s done the relief you feel, the fulfillment, will be palpable. And I know you can do it. I knew it the first time I saw you in the cafeteria.”
Where the fuck did that lightening bolt come from? “The cafeteria?” I shouted. “What fucking cafeteria?”
“The one at work,” she said. “We work for the same company.”
I was stunned. I covered my cock and balls with my hands.
“Take your hands away from there now, Ishy.” Mona said sternly. “You’re hardly in a position to get high and mighty, are you? And I can’t see any dignity that I might be offending.
“We all have to earn a living. You and I both have roles to play out there,” she said, looking at the window to indicate the world outside it. “But that’s all they are, roles to pass the time and pad the bank account. Our reality is in here. It’s where we can be who we really are.”
“I’ve never seen you at the office,” I muttered, as if that proved anything. My hands hung limply at my sides. I don’t know why but I wanted to cover myself again, like I’d just eaten Satan’s apple and felt a new shame wash over me.
“I have a low-profile position. I’m an attorney in the corporate legal department. I work on big customer contracts that aren’t the slightest bit sexy but keep the company flush. I live in the software shadows.
“But I’ve seen you a bunch of times. You’re always with that cute blonde girl. What’s her name?”
“Julie.”
“That’s right. Julie. She’s one of the few female engineering managers we have. She’s going places, you know.”
“How do you know that?” I asked.
“I make it my business to know about strong women in the company. They’re the future. Is she your girlfriend?”
I shook my head, No.
“But you’d like her to be, wouldn’t you? You don’t have to answer that. I could see it every time I saw you two together, the way you hung a few inches behind her, the way you looked at her with lollipop eyes. That’s when I knew you’d be perfect.”
“Now wait a second,” I started to protest, covering up my crotch again.
“Don’t cover yourself up, Ishy.
I dropped my hands again, and then I dropped my head so that my chin was touching my chest.
“Enough now.”
Mona turned to Carole and said, “Why don’t you get him ready,” and then walked out of the room and down the hallway.
I stood there trembling, every inch of my skin sensitive to the slightest movement in the air. My eyelids started to twitch. I tried to shut my brain down.
Carole walked across the room and took an Oriental black lacquer box from the bottom shelf of the bookcase. She came back and sat on a leather chair next to the couch and put the box on a end table.
“Come over here, Ishy,” she said. She flashed a broad Cheshire cat smile, patted her lap quickly a few times and said, “Over my knees now, with your little dingle between my legs.”
I hesitated. I’d actually never been over anybody’s knees, not even as a kid. Never been spanked. Was that what preparation meant?
“Now,” she said. “Do it.”
I walked over to her. She looked up at me. I bent over. The position was awkward but I managed to balance myself over her knees.
“Good,” she said. She rubbed my ass in a slow circular motion with one hand while rummaging around in the black box with the other. “That’s nice, isn’t it? You do have a cute little butt.” She gave me a quick light slap on one cheek and then her hand was gone.
“OK,” she said. “Reach back and spread your cheeks for me.” I did it without thinking. I didn’t hesitate for even a millisecond. Reaching my arms back made it easier for me to balance on her knees. That I noticed this struck me as a particularly perverse epiphany.
Then I felt a blob of cold lube on my anus. “A little wider please, Ishy,” she said. So I moved my fingers even closer in and pulled my ass open as far as I could. “That’s better,” she said.
Carole slowly stuck a finger in my ass and started to move it in and out. “Ahhhhh,” I said. Is “said” the right word? The sound just came out. She kept up a slow in-and-out motion for a minute or two, and then the finger pulled out. “Ooooooo.” That sound came from me. Then the finger shot back in and she started to lightly massage my prostate. “Oh my god,” I said. I could feel my cock getting hard between her thighs. She obviously felt it, too.
“You like that, Ishy, don’t you?” I made some sound; I don’t remember what it was. “Don’t you?” she said again. “I asked you a question. Answer me.” And she pulled her finger out quickly and slapped my ass.
“Yes. Yes, I like it, god damn it.” And I started to get teary again.
Carole put her other hand under my chin and lifted my face up. “You’re not going to cry, are you Ishy? There’s no reason for that. There’s nothing to be ashamed of. Men like a finger up the ass. I learned that a long time. Stick a finger up a guy’s ass when he’s fucking you and he revs up to a new level and explodes in an instant. It’s the key to the kingdom.” She chuckled out loud. “The key to the goddamn kingdom,” she said.
“And as soon as it’s over they freak out. I broke up with a guy once, when I was still doing guys, and all he was worried about was that I would tell my friends that he liked a finger up his ass. They say they’re afraid they’re gay, but that’s not it, not it at all. You want to know the real reason? They realize they can be taken, penetrated. They lie there and get plowed and it feels good. But their boy egos can’t take it that someone’s working them from behind, that their pleasure is made possible by their powerlessness.
“But you understand that, don’t you Ishy. You know that you’re most fully yourself when you’re bent over and being taken.” And she plunged her finger back up my ass, and I pushed back to let her in. Her one little finger had me moving back and forth like a rocking horse. “The key to the fucking kingdom. I love it, Ishy, I love it.”
My cock was going up and down between her thighs. “I’m going to come,” I said. “I’m going to come.”
And then her finger was gone, just like that, like Lucy pulling the football away from Charlie Brown. “Don’t come,” Ishy, she said. “You can’t come yet. That’s for later.”
Carole leaned back in the chair. I hadn’t realized how worked up she’d been. I could feel the tension drain from her body. I had to plant my feet on the floor and reach my arms out straight to stay balanced on her lap. My cock went limp.
“Sorry,” she said. “I guess I got carried away. It’s so much fun showing you boys a side of yourself you work so hard to deny. But I have to get you ready. This little rosebud of yours is going to get a workout tonight, and we want you to be prepared. So I’ve got to stretch you out a bit. Hands back, ass spread, please.”
So there I was again, holding my own ass wide open. I felt more lube added to my anus. And then I was penetrated again. “I’ve got two fingers in you now, Ishy,” Carole said. And she moved them slowly in a circular motion. It was the same kind of movement you make when turning a screwdriver in a wall to widen the hole for a screw. “I’m adding a third finger now.” And I felt the added thickness as the fingers danced a roundelay in my asshole. “Four fingers now, Ishy. Does it hurt?”
“A little,” I said.
“But you like it, don’t you? You could get addicted.”
I groaned. An “Uh” came out.
“I didn’t hear you, Ishy. Answer me.”
“Yes.” And for some reason, a fear still deep inside brought me back to when I was a little boy who thought the girls were laughing at him. I turned my head and glanced around the room to be sure there was nobody watching me shrivel in shame as my cock reached for the moon.
“Good, Ishy, that’s good.” And then the fingers left. “I’m going to put in a butt plug now, Ishy. And you’ll keep it in until the people start arriving. That’ll stretch you out plenty for tonight.”
She reached back and took something out of the lacquer box and then waved it in front of my face so I could get a look. It was a basic penis-shaped plug, about seven inches long and as thick as my own cock. But my eyes opened wide when I saw a fluffy red feather sticking out the back of the plug.
“It’s cute, isn’t it?” She started to insert the plug, and it hurt. “There’s a lot of lube in there so you’ll be fine. Just relax for me. Try not to tighten up.” She slowly pushed the plug into my ass. Once the tip was in and my sphincter swallowed it, the rest went in easily.
“Stand up now. Don’t clench too tight, and don’t let the plug fall out.”
I put my hands on the edge of the chair and carefully stood up. All I could focus on was the plug in my ass. I felt filled, stuffed really, in a way I never had before. I didn’t know if I could walk. It all felt weird.
“You’ll get used to it,” Carole said. “You should probably have a plug in for the next few weeks so we can keep that little ass of yours open to new experiences.” She must have thought that was clever because she looked at me and smiled broadly, showing a set of perfect white teeth that had probably cost her family a bundle at the orthodontist.
“Now it’s time to see how good you are with your mouth,” she said. She stood up and unwrapped the long, black skirt and then sat back down, spreading her legs. She wasn’t wearing any panties. “Down on your knees, Ishy, and eat me out. Go slowly.”
Carole’s pussy with a full bush was open on the edge of the chair. I knelt in front of her and used both hands to spread her labia and then put my head down and went to work. I lightly ran my tongue around her vagina, thrusting it in occasionally before returning to a leisurely swirl around the perimeter. Then I began to scoot my tongue up and flick her clit for a second or two before heading back down again. I kept this up for a good five minutes, gradually spending more and more time on her clit. She began to rock back and forth, and I started licking like a madman, adding some nibbling and sucking, changing direction, doing everything I could to bring her to a climax. She started moaning. “Yes. Yes. That’s it. Don’t stop.” She grabbed my head and pressed my face deeper into her pussy. I kept going, working the clit every way I knew how until her whole body went taut and she came with the force of waves crashing onto the shore.
Carole’s body relaxed and I slowly lifted my head. My face was wet from top to bottom, coated with the effluvia of her sexual triumph. I raised my arm to wipe my eyes with the back of my hand but she said, quietly, in a relaxed tone of voice, “Leave it Ishy, it’s good for your skin.”
Just then I became aware that Mona was standing behind me. I didn’t know how long she’d been standing there. She’d changed into a flowing black silk robe. “I’m glad you tried him out,” she said to Carole. “How did he do?” She laid her hand on my shoulder as if to assure me that I was more than simply a new appliance being given a test run.
“Perfect,” Carole said. “He’s a natural. I almost feel like we should keep him to ourselves and not share.”
“I’m glad to hear it,” she said. She squeezed my shoulder and then sat down on the couch. Carole got up, rewrapped her skirt and ran her fingers through her hair. “I need a drink,” she said, and took off for the kitchen.
Mona motioned me over to her and said, “Good boy, Ishy. I knew you’d be good. It’s your nature to serve.”
Carole came back with a glass of water and sat on the couch next to Mona. “Wow, that was good. I feel great.” She stretched her arms out and sighed.
“Turn around, Ishy,” Mona said. “Take your down position, forehead on the floor and ass up. Spread your cheeks.” Again, I did it instantly. I told the voices in my head to shut up; I didn’t want to hear it.
Out of the corner of my eye I could see Mona lean forward. She took hold of the butt plug and pulled it out slowly. The tip came out and I felt empty. Mona ran her finger around my anus. “Nice,” she said. “He’s nice and open. You should see your anus now, Ishy. It’s a perfect little puckered circle with an inviting opening.”
All of a sudden my emotions burst and I started sobbing uncontrollably. It was like I remembered all the humiliating moments of my life, but they weren’t spread out over time; they all came crashing down in an immediate present. The feeling was so overwhelming it threatened to drown me. “Why are you doing this to me? Why? Why?”
“Oh, Ishy,” Mona said. “Come here.” She took me by the hand and pulled me closer and laid my head in her lap and stroked my hair.
“We’re not making you do anything, Ishy,” Mona said. “There’s no force or compulsion here. You can leave anytime you want. Nobody’s stopping you.”
I looked up at her. She smiled at me.
“You’re doing this because you want to, because you need to. The shame you feel is exquisite and the pleasure you get from it is unlike anything you’ve ever known. I know it’s unbelievably humiliating, but look at yourself, you’re hard as a rock. Your cock is telling you how much you need this.
“The pleasure, the fulfillment comes from the humiliation. Think about it. What are you feeling right now? You’re mortified but every cell in your body is alive, every nerve end is tingling. Now just for one second try to imagine how much more powerful those feelings will be an hour from now when you’re on all fours spreading your ass in front of a room full of women, waiting for the first one to step into a strap-on and fuck you while the others watch and wait their turn. Your little cock is actually dripping right now. You could come just thinking about it.
“And you know what, Ishy, I need it too because the only thing that’s more fun than watching a boy be sexually humiliated is to be the one doing it to him and knowing it’s a willing partnership. I need to keep pushing you, to see just how far you’ll go, how much naked humiliation you can take, how much of your real self you can expose.
“I know this will sound crazy, Ishy, but I admire you. It takes courage to recognize who you really are and to live it. Not many boys have the guts to do it but believe me, it’s what they all want. I do love humiliating you, Ishy, but I do it with genuine affection. As painful as it is, you’re showing me the real you . . . and you get off on it. It makes me wet to watch you.
“Now Carole here, she’s different. She sees you boys as pathetic creatures who only want their mothers to rub their little boy parts. She wants to make you squirm because in her eyes it validates her natural superiority. But she would never hurt you; it’s all done with a sense of humor. Isn’t that right, Carole?”
“Yes ma’am,” Carole said with a big smile. “You know what I like best. I like watching him masturbate for me.”
“You’re incorrigible.” Mona turned back to me. “Does this make sense to you, Ishy? You can’t deny the release and the pleasure you feel.”
“I know,” I said, “but it’s so . . . it’s so . . ..”
“It’s okay, Ishy.”
“But I shouldn’t want to do all that.”
“But you do want it. You’re still here. You haven’t left . . . and you won’t.”
I just let my head drop. She was right.
“Adrenaline rush is over,” Carole said.
“It will come back,” Mona said. She stood up, smoothing out her robe. “People will be showing up in a little while.”
Carole bit her lip as if stifling a giggle. She looked over at me and then turned to Mona. “You know,” she said. “His virgin ass is going to get fucked a few times tonight.” She paused.
“Don’t you want to be the first?”
“I was planning on it,” Mona said.
She walked over to the easy chair across the room. It was a big old-fashioned leather chair with extra wide arms and a thick throw pillow, like the chairs you see in the wood-paneled library of a fancy old house (a traditional man’s room; I’m sure Mona appreciated the irony). The chair was facing directly across from the couch, looking a bit like a throne.
Mona unbelted her robe and let it fall to the floor. Underneath she was wearing a thin, white, silk blouse with spaghetti straps that stopped just above her belly button. The only other thing she was wearing was a strap-on with a seven-inch dildo.
“Come over here, Ishy,” she said.
I got up slowly and headed towards her. I couldn’t take my eyes off the dildo. It looked huge.
“Here you go,” Carole said, and tossed a bottle of lube to Mona, who snatched it out of the air with one hand in a movement that can only be called graceful.
“Your ass should be well lubed up, Ishy,” she said to me, “assuming Carole did her job. Always a safe assumption,” she said, “in matters of the heart.” And both of them laughed. “But I want you to lube my cock so it goes in nice and easy. I want you to take a good look at it.”
Mona handed me the bottle, which fell through my hands and dropped to the floor. “Pick it up, Ishy,” she said. “This is going to happen. And I want you to remember your first time.”
I was in a strange space but I didn’t want to leave. I was fully aware of what was happening. My senses were attuned to the slightest tactile details: the cold slippery lube, every fold and ridge of Mona’s cock as I rubbed lube on it.
Mona looked down and pushed a tiny button on the strap-on harness. “There’s a vibrator in here,” she told me, “just a little added benefit for me.
“Now I want you to concentrate, Ishy, I want you to feel everything. I want you to feel how much you want it. And when we’re done, you’ll know exactly how it feels to get fucked. And you’ll want more.”
We were standing to the side of the chair, the couch off to the left. I really couldn’t see Carole, and she was surprisingly quiet. Mona laid the throw pillow flat on the chair so the height of the seat was the same as the arm of the chair. “Turn around and bend over the chair.” My ass was hanging over the arm of the chair with my cock dangling in the air and my chest and face lying on the pillow.
She gave me a quick slap on my left cheek and said, “You know what to do now, Ishy.” I hesitated. “Ishy, now.” I reached back and spread my ass. “Good boy,” she said.
“Relax and it will all go easier.” She aimed her cock at my anus and slowly pushed it in until my sphincter closed around the head with a pop that I thought too loud to be good. She started to push it in deeper, going about an inch and then stopping for a few seconds before going farther. The pain was incredible. I screamed, “I can’t take it. You’re going to split me open.”
“You’ll be okay, Ishy, just relax and go with it.” She pushed all the way in and then began to pull out very slowly. The pain was excruciating. My eyes were tearing and I was crying, “Stop, stop.” But she didn’t. She pulled almost all the way out and then started to push in again. She moved in and out, in and out, slowly but steadily. Gradually the pain started to subside and I felt grotesquely filled up; it was unlike anything I’d ever felt before. I was being nailed to the chair, held in place by her cock.
Mona started fucking me faster and harder. She was plowing into me. She slapped my ass hard a few times, just to let me know, I think, that she was getting off on my helplessness while chasing her own pleasure.
Mona was fucking me like she was possessed. “Say it, Ishy, say it,” she yelled as she kept slapping my ass. “Say it. Say it, goddamn it, say it.”
And I did. “Fuck me. Fuck me. Fuck my ass.” The shame I felt at that moment was astounding. But the cock in my ass . . .
It felt good, it felt unbelievable. I was being fucked in the ass and I wanted it. Mona slammed into me and my whole body slid forward on the pillow. I started rocking back and forth to meet her thrusts; my god, I was helping her fuck me. The pleasure was intense, the shame I felt for wanting this . . . and loving it . . . was intense. I tried to bury my face in the chair and clenched my eyes shut. I was swallowed up by the physical pounding and the conflicting pleasure and shame; or not conflicting – I loved them both. And even though I’d turned away, I knew that Carole was sitting there watching Mona take my cherry, and the thought of that made me even more excited.
Then there was a popping sound as Mona pulled all the way out; I felt empty, abandoned. And then she shoved her cock back in with all the speed and power she had. I screamed, “More. Don’t stop.” And she kept fucking me harder and harder and she starting moaning out loud over and over; my cock was wagging wildly between my legs. Mona’s whole body went rigid, and she shrieked, “Yes,” dragging the one word out. She continued to rock for a good thirty seconds before collapsing on top of me. We lied there, Mona draped over me, four legs and four arms hanging still. The only movement was the twitching of my hard-on, hanging down, mocking me.
Mona slowly got off me and slapped my ass playfully. But I was riveted in place. What had I done? Who was I?
Mona rolled me over and helped me scoot up so I was leaning against the chair, almost standing but not quite. My eyes were still closed; I don’t know why but I was afraid to open them.
“Oh, Ishy,” Mona said. “You did great. And you liked it. I know you did.” But you’re still hard. You want to come, don’t you? Tell me.”
I shook my head. “Yes.”
“Then do it,” Mona said. “Keep your eyes closed and concentrate on how much you want to come. But remember, you’re doing it for me. It’s nothing if I don’t watch. I need . . . we need . . . to see you masturbating in front me after I fucked you.” She took my hand and ran it along the dildo to get some lube on my fingers. “Go ahead, Ishy. Make yourself come now. But tell me right before you come.”
So I started to rub my cock up and down slowly, my head spinning as my eyes shut tighter. My hand moved in the comfortable, practiced motion I used when I was alone, finishing by making slow circles on the inside part of the tip of my cock until the pleasure was almost unbearable. “I’m going to come,” I said, “I’m coming now.”
“Open your eyes and look at me, Ishy. I want you looking in my eyes when you squirt.” And that’s exactly what happened. I squirted and squirted and kept squirting. It had never been like that before, so much come, so strong. And then my head fell to my chest. I was still holding my cock, come seeping through my fingers. Mona took my hand from my cock and lifted it to my lips. “Lick it, Ishy, lick up your come.”
And I did.
Then Carole yelled, “Woo hoo,” and started clapping wildly.
I looked over at her and thought I saw someone else with her on the couch. My vision was a little fuzzy so I blinked a few times to clear my sight.
And there, sitting next to Carole, was Julie.
“Oh my god. Oh god, oh god, oh god.” I fell to my knees and wrapped my arms around myself, shaking like a child woken up in the dark by a nightmare.
Julie got up and walked over to me. She put a finger under my chin and gently lifted my head and looked at me. The expression on her face was ice cold but there was the faintest whisper of a smile. Without taking her eyes from me she said to Mona, “Can I fuck him in the ass?”
