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“Eight years,” I thought as I left Jennifer’s office. “Eight. Years. Eight. Fucking. Years. And she pulls this shit. Who the fuck did she think she was? If I wanted this, I would have gone to a dominatrix. It would’ve cost me a hell of a lot less, and I wouldn’t have wasted all those lunch hours.”
I could feel myself scowling and clenching my fists. I must have made some sight walking down Broadway to the train. “Fuck her. Just fuck her,” I thought. A woman stared at me. I glowered back. Out of the corner of my eye, I saw her shake her head as she scurried off.
As I passed 74th Street, I heard a woman’s voice, “Steve?”
I snapped out of my misery, “Huh? Yeah...holy shit! Donna? Donna Amalfitano?” I said with a smile. Donna had been the high school and community college girlfriend of my friend Dan Quinlan. We all hung out together when I was back from college on breaks.
“Donna Hicks, now. But yeah, it’s me.”
“Oh wow, it’s been, what, like fifteen years? I thought you moved to San Diego back in 1990.”
“I did. But I came back. My job gave me a chance to come back, and I missed my family. I have a niece and nephew now, and I felt like I was missing out on their lives being cross-country.”
“That’s cool. How’s your family? How’re your mom and Nick doing?” Donna’s dad died when we were juniors in high school.
“Mom’s fine. Nick just got promoted to sergeant on the force.”
“The force? As in police force? Nick? Your brother Nick?” Nick had always had, let’s just say, a difficult relationship with the law.
“Yup, he’s a cop now. Has been for twelve years.”
“Wow, I guess people can change, huh?”
She laughed. “I didn’t say he’d changed. I said he was a cop.”
“Oh. Enough about him. So tell me about the lucky Mr. Hicks.”
She blushed. “Thanks, Steve. I appreciate that. Not much to say. We’re divorced. And you?”
I held up my left hand and tapped my ring. “Seven years or, as I like to put it, two wonderful years.”
“Really,” she said, arching her eyebrows. “That’s, uh, great.”
“What?” I said, girding myself. “What does ‘uh, great’ mean?”
“Nothing,” she said. “Forget I said anything.”
I knew what she was talking about. Back when I was a freshman in college, she attended community college with my friend Quinlan. His given name was Dan but, at some point in high school, everyone started calling him just Quinlan. Teachers, his brother, everyone. Only his mother and father called him Dan. Anyway, I was back on winter break my sophomore year and we were all hanging out.
“Hey, Steve,” she asked. “Do you know anything about American History from 1900 to the present?”
“Kind of a broad area, but yeah I basically do. Why?”
“Well, I’m taking this history class, and my final’s coming up.”
“OK, what do you need? Help studying.”
“Yes,” she said, suddenly grinning. “Actually, I have a better idea.”
I rolled my eyes, “This should be good.”
“We’ll dress you up like me,” she said, cracking herself up. “Leggings, a big shirt. A wig. Makeup. Noone will know.”
I began to sweat, or at least feel like I was. I regained composure. “Great idea. How do you suppose will pull this off? I’m, what, 6" taller and like 50 lbs. heavier than you? Besides, what do we do about Mr. Lucky down there?” I said, pointing at my crotch. Deep down, I was really excited. I wished we could do this.
She pulled out a compact from her bag, and began dusting my face with powder. I was getting more and more excited. “Oh, we could pull this off. So you’ll wear a skirt instead,” she said, looking down at my rapidly growing member. “I mean, if that wouldn’t bother you too much.” I blushed. I knew exactly what I’d wear. She had a black cotton miniskirt and boots that I loved. That, her cute blue top, some bracelets. I was getting really excited.
She giggled. “You would be really cute. And look you won’t need blusher.”
Just then, Quinlan walked in from the bathroom, “What’s going on?”
“I had this great idea for Prof. Rabinowitz’s class,” she said, laughing. “We’re going to dress Steve up like me, and he’s going to take the final.”
“That’s a good idea,” he laughed back. “I mean, so long as I don’t have to sleep with him after or anything.”
I got up, and punched him in the arm. “Yeah, like I’d sleep with you, you dickwad. This is nuts,” I said, protesting too much. “I’m going to wash my face.”
Donna came over. “I was just teasing, Steve.”
“Yeah, I know,” I said. “Besides, I’m a lot of things, but an attractive woman isn’t one of them. Anyway, I’ll help you study, if you want. Let me know when.”
“How about tonight? The test is day after tomorrow. I’d really appreciate it.”
“No problem. Not like I have plans.” Which was, unfortunately true. I got together with friends from college on the weekends, but during the week I reverted to my high school loser self.
That night, I went over to Donna’s to study. I rang the bell. Her brother Nick answered.
“Hey, Nick, how you doing?”
“Hey, Donna, your girlfriend is here,” he sniggered.
She came down the stairs, and punched Nick in the stomach. “Shut up, asshole. Hi, Steve. Thanks for coming over.” Nick stared at me, shook his head and said, “I’m going out. Ladies.”
“You didn’t have to do that,” I said. “I don’t put too much stock in Nick.”
“He’s just a dick. Let’s go to the kitchen.”
We studied for several hours. Donna wasn’t stupid, by any stretch of the imagination. She just had no ambition, which was kind of to be expected. The women in her family worked as secretaries and store clerks, and said of any woman who tried to do better “Whaddaya think you’re special?”
After about three hours, she said, “You know, Steve. You’ve actually made this interesting. I think I could do well on this test.” She leaned over and kissed me chastely on the cheek.
I blushed. “Thanks, this stuff really interests me. Besides, you’re smarter than you think.”
“Thanks,” she said. “You’re really a great guy. And I want to thank you.” She reached into her purse.
“You’re welcome,” I said, “You don’t have to give me anything. It’s really no big deal. I like helping you.”
She pulled out her address book, and wrote a name down on a piece of paper.
“What’s this,” I said, looking at the paper.
“It’s my cousin Todd’s number. He’s a sophomore at Yale. I told him all about you. He’s really excited. He likes intellectuals, especially blue eyed ones.”
Subconsciously, I wanted to squeal with delight like her girlfriend. I wanted to ask her all about him, what he looked like, what he liked to do and all of that. But I was in deep denial, so instead I growled, “What? What’s this supposed to mean?”
“I just thought...” she said.
“You thought wrong,” I snapped. “I’m not gay or anything. What the hell made you think that?”
“I’m sorry,” she said. “It’s just that you’re smart and funny. And no one’s ever seen you with a woman. I mean, you don’t try and hook up when we’re all out or anything.”
“So what, Dean and Lucas never hook up. Do you think they’re gay too?”
She rolled her eyes. “Please. Come on. Lucas tries to hook up, but he’s not exactly fuckable, if you know what I mean. And, Dean is, well, Dean. He’s in his own world. Don’t lump yourself in with those two. You’re better.”
“Thanks, but even still...maybe I’m just shy, did you ever think of that?”
“Maybe, but you talk to me and Erica. You’ve talked to my friend Sheri. She was into you, you know. All you had to do was make a move, and you didn’t.”
“First off, I talk to you guys because you’re my friends’ girlfriends, so I don’t feel subconscious or anything. Plus, Sheri was really into me? Really?”
She laughed, “OK, maybe you’re not gay. Just dense. I mean, if you were gay, we’d be cool with it.”
My eyes widened. “Oh, jeez, we? Who else did you share this with? Not Quinlan, please?”
“No, no,” she said, holding my hand. “Quinlan would be all freaked out. I told Erica.”
“Oh no, she’ll tell Jason, and he’ll tell Quinlan,” I groaned.
“No, she won’t. She understands. She’s totally cool with it...”
“There is no it to be cool with, Donna. OK?”
“OK, OK. I’m sorry. I didn’t mean to hurt your feelings. I just thought...”
“I know. Next time, remember, I like women.”
“Yeah, OK. Whatever...”
After that, whenever we all went out, I made a real effort to try and “hook up,” or at least look like I was. It felt like I was acting, and acting poorly, and not surprisingly I always struck out. I’d catch Erica and Donna out of the corner of my eye, staring at me and shaking their heads. Whenever I’d come back to the table, Donna would always say something like, “Boy, Steve, you have no luck with women. I wonder why. Just bad luck, I guess, huh?”
“Hey, Steve,” Donna said, snapping me out of my reminiscence. “I bet I know what you were thinking about.”
“Yeah, yeah.”
“Do you live around here?”
“No, actually coming from therapy. My shrink’s on 72nd.”
“You’re in therapy, huh?”
“Yeah, everyone in New York is. You’ll start soon. Or else you’ll have to move back to Jersey. It’s an obscure law.”
“No kidding,” she laughed.
“Yeah, anyway, you look like you were on your way. Let me give you my card,” I said, fishing through my briefcase. “We should get together sometime.”
She looked at the card. “Attorney, huh? I figured you’d do something like that. Actually, you would’ve been a great writer too.”
“Thanks. All lawyers are frustrated writers. Except for litigators. They’re frustrated actors.”
“What kind of law?”
“Municipal bond financing.”
“Wow,” she said, “That sounds, really, uh, exciting.”
“Yeah, I know. It’s not. But good job faking it. All those years with Quinlan must’ve paid off.”
She laughed. “Actually, what are you up to now? I mean, if you don’t have to get home or anything.”
“I was just going to get something to eat. My wife goes out with her friends on Wednesdays.”
“Mind if I join you?”
“That’d be great. Otherwise, it’s just me and the New Yorker.”
“Terrific. How about Italian? Oh, shit...not you, too, Steve,” she said, staring at my face.
“What? What me too?”
“The lipstick, Steve,” she said, angrily, “Therapy, huh? Yeah, my ex used to get the same kind of therapy. I guess I was wrong about you.” She turned to walk away.
“Wait,” I said. “It’s not what you think. Believe me, it’s not.”
“Oh really,” she snarled. “What is it then?”
“This is really, really private,” I said, with tears in my eyes. “I don’t want to talk about it on the street. Please believe me.”
I must have convinced her with my tears. She said softly, “I live on 75th and Amsterdam. God help you if you’re fucking with me, though.”
“Believe me, I’m not,” I pleaded. “When I tell you what’s wrong, you’ll know.”
She cracked a smile, “Well, this is getting good.”
I have no idea why I wanted to tell her. Maybe it’s because of what had happened between us. Maybe it’s because I knew her but, fifteen years having passed, I didn’t really know her. Maybe I just needed to tell someone, anyone. We came to her building, and walked up to her apartment.
“Home sweet home,” she said, flicking on the light.
It was a small one-bedroom. Very tastefully decorated. Very feminine. Not Laura Ashley explosion feminine, but you knew a woman lived there. Actually, if you knew Donna, you knew she lived there.
“Nice place,” I said, looking around. “I like your style. My wife’s not much for decorating.”
She gave a half smile. “Thanks. I figured you’d like it.”
I laughed, “I won’t even say, ‘What’s that supposed to mean.’”
“So, what’s with the lipstick?”
“Can I get a drink first?”
“Wine?”
“Great.”
She poured two glasses, and gave me one. “So,” I said, “this is good wine. What kind is it. And, boy, these are nice glasses. Crate and Barrel. I like Crate and Barrel.”
“Nice try, Steve. Speak or get out.”
With that, I let loose. I told her all about my fantasies. I told her about the dress. I told her about Tom. About how his massage made me feel better than I had ever felt. About his chest. About his gorgeous abs, and I how wanted to touch each muscle forever. I began telling her about how he penetrated me through the panties. I told her about blowing him. Everything.
“Whoa,” she said when I finished. “Well, that certainly explains the lipstick.”
“Shit. I’m sorry. I should never have said anything.”
“It’s OK, Steve. I’m not so sure what I think of your therapist though. That’s a little, uh, fucked up, don’t you think?”
“I’m not really sure what I think, or what’s right, you know.”
“Go with how you feel. How did it feel when he penetrated you through the panties?”
“Oh, jeez. This is, uh, god, shit. Never mind.”
“Speak,” she demanded. “Just tell me what you’re feeling.”
I stared at the floor. “I felt it in the pit of my stomach. I’ve never cum like that,” I said, blushing.
“You are so lucky, bitch. Most women rarely ever have orgasms like that. And you got it with your first try.”
“Great. I’m a woman now. Just what I wanted to hear.”
“Stop it, Steve. How was everything else? What did you think of the blow job?”
“Taking notes?”
“Stop being so sarcastic. How was it?”
“I gagged.”
“Don’t worry. Everyone does. It takes getting used to.”
“There’s no getting used to anything. It was a mistake.”
“Was it? Come on.”
I began bawling. “What the hell am I going to do?”
She came over and hugged me. “It’s OK, Steve. It was OK fifteen years ago. It’s OK now.”
“But, it’s not fifteen years ago. It’s now. I’m married. I have a job. I have a life. And this will fuck it up royally.”
“It will not, Steve,” she said, continuing to hold me. “I know your family. They’ll support you no matter what.”
“It’s not that simple...”
“Steve, I know. Remember my mom? Mass every day? What do you think she did when I told her I was getting divorced?”
“It’s not the same. It’s not like you had to announce to the world ‘I like sucking dick.’ Besides, I didn’t notice eleven states passing constitutional amendments against divorced women...”
“Yeah, OK, I see what you’re saying. But, still, you need to be happy. You need to be who you are.”
I started bawling again. “I don’t know who I am anymore.” She came over, held me and wiped a tear from my face. She leaned in and kissed me gently on the lips. “There, there,” she said. Then, she kissed me again, harder. I opened my mouth and our tongues began probing the inside of each other’s mouths.
She pulled back. “You kiss nice. Soft. Gentle. I like that.”
“Boy,” I said. “Soft and gentle. I feel good now.”
“Shut up,” she said, kissing me full on the mouth again.
I stopped. “I don’t know. I don’t what else I am, but I know I’m still married.”
“That’s fine,” she said, coyly. “Whatever you want.”
I grabbed her, and began kissing her.
“Gently, Steve. I liked it gently. Let me control everything.” With that, she began kissing me forcefully. She put her hand on my groin. “Looks like someone still likes women, too. Come this way,” she said, wagging her finger towards her bedroom.
I shouldn’t have done it. I owed Beth that much. But I did. I went with her.
She pushed me onto the bed, and began taking my shirt off button by button. She ran her fingernails up and down my chest. “Mmmm, do you like, Stevie? Mmm, do you, little girl?”
“Unnnh. Yeah. Mmmmm.”
“Yes, good little girls say ‘yes.’”
“Oh, yes. Donna. Oh, yes,” I moaned.
Then she unbuttoned my pants. “Oooh, someone’s enjoying himself.” I tried to sit up, and take off her blouse. “No, no, no,” she said, pushing me backward and straddling me. “I’m in control, you little, what did you call yourself, bottom. I like that. You’re my little bottom.” With that, she reached up under her skirt and pulled off her panties. She threw them at me. “Smell. You like?”
I took in her musky scent. I loved it. I had always liked going down on Beth. She didn’t like it though. “Mmmm, you smell great.”
She brushed my penis with her vagina.
“Please, Donna, please,” I cried.
“No, no,” she said, inching her way up my chest, “Remember, you’re the bottom.. I’m the top. You will do what I say when I say it.” With that, she put her pussy over my face. I began licking her clit.
“Faster, now slower, now faster,” she said, as she fingered her nipples. “Ooooh, that’s good. Oh, yes, Stevie girl. Oooh, you know what to do.” She jerked involuntarily. “Yes, yes. Yes, yes. Oh, Stevie.”
She crawled off me, and reached into her nightstand. She pulled out a baby doll nightie and a condom. “Put these on.”
I put on the condom. I held up the nightie, “But...”
“Little girl, do you want me to do something about that?” she asked, pointing at my penis.
I reluctantly put in on. It was tight, but it fit. She pushed me onto my back. “Now, put your legs on my shoulders. I’m going to fuck you the way you need to be fucked.” This was one of my deepest fantasies, to have a woman fuck me while I was in a nightie. If she’d throw in handcuffs, I would’ve truly been in heaven. I kept expecting to wake up.
She began rhythmically pushing herself on and off my penis. “That’s good,” she said. “Feel the motion. Start pushing back with just your little pussy there. That’s right. That’s right.” Then, suddenly, she began putting her finger in my asshole. I jerked.
“Calm down, little girl. Relax. Do you like it?” she said, thrusting it in out, while we rocked in time.
“Oh, yes. I like it,” I whimpered.
“Which do you like better?”
“Both, I like both.”
“Say, ‘Fuck me. Fuck me harder.’”
“Fuck me. Fuck me harder. Please fuck me.”
“Nice. I like that.”
“Who’s my Stevie? Who’s my little girl?”
“Me, Donna. Me. Please don’t stop,” I said, arching my back.
“Good girl,” she said. “You know just how to please me.”
I jerked my back one more time, and came violently. “Oh, Donna.”
“That was a quite a little performance there, Steve. You are one little rug muncher. If you switch sides, it’ll be a real shame. Although, there will be some lucky guys.”
That snapped me out of the post-coital glow. “Oh, shit. What did we just do, Donna? Oh, god, look at me,” I said, turning to the mirror.
“Do you like what you see?”
“It doesn’t fit right. But, I like the way it looks and feels.”
“There’s nothing wrong with that.”
“Would you be with someone who liked it?”
“I just was.”
“Pity fucks don’t count.”
“I don’t do pity fucks, Stevie. Don’t sell yourself short.”
“What the hell did we just do?”
“Are you happy at home, Stevie?”
“Not really.”
“I’m no shrink, but you seem lost. Like someone trying to find his way.”
“Wow, that’s deep...” I said, with a smile.
“I’m trying to help.”
“Sorry. You’re right, though.”
“How many women were you with before Beth?”
I didn’t answer. I looked away.
“Were you a virgin?” she said.
“No.”
“Don’t lie.”
“Yes.”
“Whoa...sorry, that was mean. How many men had you been with?”
“Before today, none.”
“Wow, you really don’t know what you are, do you?”
“I just want to be happy. To be with the right person. Whoever, or whatever, that is.”
She kissed me again on the cheek. “I want to help you, Stevie. Figure out who you are. Whoever you are, I like you. I always have.”
“Thanks,” I said, “What the hell do I do now.”
“Go home. Don’t do anything rash. If you need anything, call me.” She took a piece of paper. “Here’s my number.”
“Thanks,” I said, taking off the nightie and getting dressed. “Now, I’m really fucked up.”
“You’re just confused. Go.” she said, putting on a t-shirt and shorts.
As she took me to the door, she kissed me again. “Seriously, if you need anything, call. By the way, Todd’s still available.”
“Ha, ha,” I said, with a smile. “Besides, how good could he be if someone hasn’t snapped him up yet.”
She laughed, “You are such a bitch, girl. Leave,” she said, pushing me out the door. “Anytime you want to go down again, let me know. You have one hell of a tongue,” she said, as the door closed.
I walked downstairs. The world seemed all at once better and worse. What the hell was I going to do now?
{to be continued, if there’s interest.}
Comments
I'm enjoying the story and lo
I'm enjoying the story and look forward to future chapters.
Me too...
Excellent please more.
JC
The Legendary Lost Ninja
Jennifer/Tom ???
<< How many men had you been with?â€Â
“Before today, none.†>>
I don't get it. At the beginning he was coming from Jennifer's office, mad at her. Was jennifer the therapist and she hired Tom to fuck him?
"All the world really is a stage, darlings, so strut your stuff, have fun, and give the public a good show!" Miss Jezzi Belle at the end of each show
BE a lady!
Excellent Story
I'm enjoying your story very much. I look forward to many more excellent chapters. You've got me hooked so please write more.
John (dooey52)