I got home after another long day at work and retrieved the mail. I sifted through it…junk, bill, junk, bill….
“What this?” I wondered, looking over an envelope with no return address. “Hmmm?”
I took it upstairs to my kitchen and opened it. Carefully. It contained three handwritten pages of pink paper. I read the first one, a brief cover letter, as it turned out.
I wrote this letter the day I got home after Marcy’s wedding, but it took me months to get the courage to mail it. I’m not sure I should have, but, if you’re reading it, I guess I did.
That’s all that page said. I started pacing the floor. I remembered that wedding well, but the reception was a little blurry. I know one thing, I made a total ass of myself. (Fucking tequila!)
I took a quick peek at the next page. (I had a sneaking suspicion.)
“Yep.” I muttered, suspicion confirmed. Her handwriting was pretty distinctive, right down to the little heart she drew over each “i.” But mainly it was the fact that SHE was the only one I ever let call me “Stevie.”
I sat down. I had figured I’d hear from her again one of these days, but now I was a little afraid to read the letter.
“What if she says she doesn’t ever want to see you again?” I said to myself, as my mind wondered back in time to that wedding.
Marcy was an old high school friend of mine. I’d been out of the loop, so I was surprised to get the invitation. The only reason I went (it was about two hours away with a lead foot) was to see if SHE would be there. I knew she’d been out of the loop, too, but if I got invited….
I had made the trip to the wedding with time to spare, but was a little late (conveniently) in arriving at the church, so I just sneaked into the back row. I saw a few familiar faces, but not many.
I started thinking about the glory days. It had been 12 years since high school. I always thought I was pretty cool back then. I played sports, was a class officer, always got invited to the best parties, shit like that, but now…. Here I am sitting in the back row of the church, no wife, no kids, no date, a lame ass job, a way-too-old truck, and $7,000 of credit card debt just to top it all off. I wasn’t 100% sure about high school, but I knew I was anything but cool now. I wondered how things had turned out this way for me.
I was lost in thought.
I suddenly realized that people were standing and clapping. I joined in and followed the wedding party out into the parking lot. A pretty redhead caught my eye.
It was HER.
And she was still the hottest thing on two legs.
I kept her in my sights, but tried to stay out of hers, because she was holding hands with her husband.
“What a dick,” I thought. “Why him?”
I continued to watch them (while everyone else focused on the bride and groom). They seemed like a happy, good looking couple. I followed them until they hopped into a shiny blue Escalade. (He even opened her door.) I huffed and headed for the reception. Once there I went right to the bar….
And so it began.
I was working on my second beer when our eyes met.
“Oh-my-god!” Debbie ran over to me and wrapped her arms around me. I held her tight. (She is the only woman to ever make me weak in the knees.)
“Ok, break it up, you two.” Her husband pried us apart with a friendly smile. “How’s it going, Steven?”
“Alright. Good to see you, Mark.” (It wasn’t.) We shook hands. The three of us made some friendly conversation before Mark suggested we find our seats. Debbie gave me a quick kiss on the cheek, and they moved into the hall. I went back to the bar and grabbed another cold one — and a shot — before finding my seat at the back of the hall.
It was a normal wedding reception (white people dancing badly), but I just couldn’t get Debbie out of my mind. I thought about our past.
Debbie grew up next door to me. We were same age, so we rode the same school bus. We became fast friends. People used to joke that we were Siamese Twins because wherever I was, Debbie was, and vice versa.
Debbie often used to sleep over at my house. (My mom and I lived in the lower floor, and my Aunt and her kids lived upstairs.) But it wasn’t like at a kid’s sleepovers. She used to sneak into my bedroom through the back door and crawl into bed with me, mostly on weekends. I don’t remember exactly when it started. I just always remember it happening. My mom knew, too. When I’d ask to eat breakfast in my bedroom, she’d joke, “Are we having breakfast for one or two today?”
Only when I got older did I understand that Debbie was fleeing from home more than wanting to sleep with me. She didn’t talk about it much, but I knew she wasn’t happy at home.
When we got into high school, our sleepovers slacked off, but they still happened. I was trying to “take our relationship to the next level” (as they say), but she always said that she wasn’t ready for sex, and I never pressed her, even when I woke up and found her in my bed. It was difficult, especially when she blossomed. Sometimes I’d wake up with morning wood and find her sleeping in these little short shorts and a small tank top. It was all I could do not to…. It was all I could do.
But, otherwise, things generally seemed fine between us. I’d always thought we were a couple until the night of the Bradford Halloween party, our Senior year. Debbie said she was working late (she worked part time at some clothing store), so I stayed home for most of the night giving out candy. Then I hit a couple of hot spots before going on to the party.
Things were kind of quiet, and something just didn’t seem right. People were looking at me strangely. A friend of mine even tried to stop me from going upstairs to the finished attic — where all the couples went to make out. I got this sick feeling. I brushed past him and raced upstairs and searched room after room, until I opened one door, and there she was…there THEY were. Debbie in bed with a boy on top of her. They froze. She wore a look of panic on her face, but she never said a word. I looked down at the trail of discarded clothing, and then back up to his arched back. Even under the covers it was obvious what they were doing.
His head slowly turned in my direction. Like a punch to the stomach, I saw that it was Mark Thomas. (Mark was my nemesis. He was a year older and always seemed one step ahead of me. And, to make matters worse, he was also my cousin, who lived upstairs from me.) His face slowly grew a smile, and he resumed thrusting his hips. He had won again and he knew it. Evil thoughts filled my head. I stepped towards the bed. Suddenly, I was hit in the back of the head by something and then all I remember was being kicked, over and over.
(Yeah, that was a Halloween party to remember. I lost my girl and, thanks to a couple of Mark’s friends, sustained three broken ribs to boot.)
Debbie tried to explain, saying she was really in love with him, while she and I were just best friends. She said if I truly loved her, I’d understand….
Even though I was crushed, I tried to suck it up and be a man. I even went to their wedding a couple of years later. While we didn’t see each other much after that, we still got together at Christmas. It was never easy. I’ll admit my smile was fake, but I always thought that one of these days she’d see who truly loved her.
Then, about five years ago, Mark got a new job, and they moved away. That was the last I saw of them until Marcy’s wedding.
I finally built up enough courage and sat down and read the letter.
Dear Stevie, It was so surprising so see you at that weeding. I used to think about what I’d say if we ever met again, and then we do and I just couldn’t seem to find the right words. You didn’t seem to have the same problem, although some of them were slurred, but you still had that look in your eyes. I know it well.
That’s why I had to write this. It’s time.
Believe me, I’m not that special. I have my flaws. I know I leaned on you pretty hard back when we were younger. You were my savior. You showed me that all men weren’t perverted like my dad. I know you think he used to do “things” to me but he didn’t. But that’s not saying he wasn’t fucked up. I can’t believe I’m going to finally tell you this but here goes.
Most of the time my dad was pretty normal, but when he’d been drinking he’d get weird. One of his things was to watch my step-mom strip naked. Sometimes he’d bring his buddies over to watch too. He made me watch too. If I didn’t, he’d threaten to give me a bare bottom spanking. Even though I didn’t like her that much it was still hard to watch them humiliate her. Sometimes they’d make her touch herself or put things inside of herself.
He also used to have sex with my step-mom anywhere in the house at any time. If I was around, he’d call me in to watch, and that’s why I’d sneak over to your house. If I wasn’t around….
I knew why he was making me watch, before he ever told me. He was training me. He said the day I turned 18 I’d take her place, but he, you know, had that accident. Things were good with me and my step-mom after that. Strangely, it was a real blessing.
I guess you always knew something weird was happening over at my house, so I guess my confession doesn’t shock you that much.
It didn’t shock me, but it wasn’t what I thought. I would have loved to have been a fly on the wall, though. Her step-mom wasn’t much of a looker, but she was really built. Her dad, however, always gave me the creeps, and I knew things were weird for her at home. I was kind of happy when he died. Now, I’m thinking Debbie was, too. It made me feel better about it.
I flipped to the last page and read on.
And that brings me to you.
You were always there to comfort me. You were my rock. Not once did you try any funny stuff after I said no. Sure, I knew you took some peeks under the covers, but that was it.
I’m not sure what I would have done If you had “charged” me for my visits, but I’m sure I would have done just about anything to get out of that house.
But that’s why I loved you so, because you didn’t.
But there is “love” and then there is “in love.” I know you’ve told me more then once that you loved me. (Fifty times at the wedding.) It always warms my heart.
But, did you ever think you just might lust me?
I wonder: If you had a do-over what would happen? If you knew that last time I snuck into your bed would in fact be the last time….
I know we can’t go back in time, but I had an idea that might just square things between us.
Once a year (the last weekend in October) my husband goes away fishing, and that time is near. I would never cheat on him. I vowed. But, if something happened, and I didn’t have a choice, then I guess that wouldn’t break my vow. I’d never tell anyone if that happened. Mark thinks he’s been the only one.
Confused? Well, last Halloween a good friend of mine told me she was awakened by a large man wearing a Halloween Mask. He had this large knife, and, well, you can guess the rest. But he didn’t hurt her. In fact, it turns out he was an old flame. She was pissed, but ultimately understood. I know it happens, but still sometimes I forget to lock the back door.
“What the ….” I cried out. I read the ending of the letter ten more times to make sure it said what I thought it did. Putting the letter down, I looked at the wall calendar. I had four days to prepare.
I snapped on the small lamp on the nightstand and slid onto the edge of the bed. Even sleeping, she looked like a princess.
Moments later, her eyes fluttered open, and she let out a gasp. She tried to shuffle away, but I grabbed her by her blue nightshirt and put the knife to her throat.
“No screaming, or I’ll use this.”
“Oh, god, Stevie, that better be you,” she squealed.
I pulled the knife away. I was a little confused. I just shook my head.
“How did you get in here? I mean, I locked the door.”
“Quiet bitch!” I snarled, flashing the knife. “Or I’ll slash you.”
She let out a giggle, her eyes directed to my obviously plastic knife. (I bought it at a joke store. I didn’t trust myself with a real one.)
“Okay, maybe scratch you,” I said with a chuckle, taking off the Gene Simmons mask (same store), although I didn’t know what was going on. I mumbled, “Wasn’t I supposed to be some masked man?”
“Yeah, it was kind of scary when I first woke up, but then I remembered you were a KISS fan.” (She hated them.) “But that’s why I locked the door. I mean, I changed my mind. How did you get in anyways?”
“French doors are pretty easy with a credit card. But forget that. What do you mean you changed your mind?”
She looked down. “Yeah, I mean, I can’t go through with it. I thought I could, but now…. It just wouldn’t be fair to Mark. Right before he left he finally told me he’s ready to start a family. I’m going to be a mom. I’ve waited so long.”
“Fuck that!” I snapped, starting to get hot. (I’d waited even longer!) “What wasn’t fair was making me sit there and watch him marry you; THAT wasn’t fair.”
She closed her eyes and shook her head. I knew she was tired of hearing it.
I shrugged. “Yeah, but what’s done is done…. Is that it?”
She nodded, looking away. I started pacing the floor alongside the bed. “I drove seven fucking hours, and now you say you’ve changed your mind, just like that.” I snapped my fingers. “No, not this time. I’m done being kicked aside.”
“Please, Stevie, let’s talk,” she pleaded, pulling the covers up.
“No, this time you listen to me.” She tried to interject, but I snapped my fingers again. I ripped her covers away. She wasn’t going to hide from me anymore. She gasped and slid up to a sitting position.
“Listen, Debbie, all those years, we were inseparable, and then you chose him. Okay, I’ll live with that. I guess he treats you okay, and you two seem to be doing well. (He owned his own company, and she had some fancy marketing and research job.) But you still owe me one. You must know that. That’s why you wrote that letter…. Guilt.”
She shook her head, a tear rolling down her cheek.
“Yeah. You must remember promising me that I’d be the first. Well, we know that didn’t happen. You said in that letter that I could have a do-over. That’s what I want…that’s all I want.” I was having trouble keeping my composure, a tear joined hers.
“But we can’t. Not now.”
“We can, and we will.”
She smacked her lips. “What…? Have you been drinking?”
“No, not tonight. Tonight, I want to remember everything that I say and everything that happens, unlike that stupid wedding.”
“You were a dick. You even said you should have charged me to sleep in your bed. I know you didn’t mean money.”
(My face flushed, embarrassed that I’d actually told her that.) “Yeah, maybe. I guess I’m not the nice guy that gets walked on, anymore.”
“Well, I liked that nice guy.”
“Oh, yeah, that guy got lots of lovin’. I got to first base the same night I lost my cherry…. Fucking Prom Night. Now, I couldn’t even tell you her frigging name. It was so special.”
“I think it was Samantha.”
“Gee, thanks. I’m sure I rocked her world. It just dawned on me that I’ve never even kissed you on the lips.”
“So, you want a kiss?” She blew me a kiss.
“And that I’ve never seen you naked.”
She didn’t say anything this time. I know I was being a whiny brat, but I just wanted some satisfaction. I’d also waited a long time for this, and I figured this would be my last chance. It was time.
“So, are you prepared now?” I said, raising my voice, “to show me that bod?”
She answered by pulling her night shirt down over her knees and shaking her head. “Please leave.”
“Jesus! I always believed you when you said you weren’t ready for sex, but now, I know you’re no virgin. Just let me fuck you, once. Like you promised me many years ago.”
“But, I’m married now.”
“Yeah, you’ve pointed that out. So it will be our little secret. You know I can keep a secret.” (I’ve never said a word to Mark about our sleepovers — even after.)
“B-b-but,” Debbie stammered and sniffled. “That was a long time ago, and nothing happened.”
“Yeah, I know that all too well. But to this day you’ve never really thanked me for that. I mean, guys would have killed to be in my position. Do you know how hot you were…and still are? Wow, the things I could have had you do. Like you said in your letter, you would have done just about anything to get out of that house. I should have been the one to show you the joys of sex.”
“B-b-but, I wasn’t ready.”
“Bullshit! Maybe when we were younger, yeah, but what about high school? You weren’t that innocent.”
She rubbed her chin like she was trying to think what I might know.
“Like, I know about that clothing store.” I winked at her.
Her eyes flew open.
“Oh, yeah, I know what you used to do with that manager guy, under his desk.”
“H-how? I mean, what…?” Debbie seemed flustered.
“Wendy told me. She seemed to take pleasure in the pain it caused me.”
“Sure, it wasn’t until years after you married that she told me.” I shook my head with a chuckle. “To think, you blew the guy for a night off, or to leave early…. Wow, Debbie.”
Her face turned pink. She whispered, “It was nothing. What else did she tell you?”
“Oh, concerned now? I guess Mark wasn’t the only one….”
“I didn’t sleep with him. It was just….” Debbie’s voice sank, “Oral.”
“You sucked his cock.” I snapped, and, just to be lewd, I added, “And swallowed his cum.”
“Ewww,” Debbie groaned. “It wasn’t, like I said, it was nothing, and I didn’t swallow.”
“Nothing, huh? Ok, then where was my blowjob?”
“Yeah, if it was nothing back then…then why when I asked was it? Hmmm? I couldn’t even get you to give me a handjob after my 18th birthday party. Am I that repulsive?”
Debbie closed her eyes. “No. You know you’re not.”
“Gee, thanks.” I raised my voice. “Yeah, you know how many hardons I had to wish away. I always thought it was some sort of phobia or maybe you weren’t that type, but now I know differently. No, tonight I’m not leaving here until you’ve sucked me and….”
“I’m not having sex with you, and that’s it,” Debbie shouted. “And I’m not doing that with my mouth either.” She paused. “You’ve changed.”
I looked into her puppy dog eyes. I guess I had because usually they would melt me, but not tonight. I had to think. I’d said too much and gone too far to stop. After a couple minutes of thought, I pulled out her letter and read it out loud. When I finished, I added, “This is your letter, inviting me, the weekend your husband goes fishing?”
“Yeah, so?” Debbie sounded concerned.
(I thought, “This just might work.”) “Well, what if I showed this to Mark and told him what a great time we had living out your masked intruder fantasy. He must know about it.”
“What?” Debbie screamed out. “You wouldn’t!”
“Yeah, it would be a little lie, but with this letter…. I’d tell him how I came in with my shiny steel knife and scary mask and tied you up and fucked you silly on his bed. Just like I do every time he goes away. I’d also tell him how much you enjoyed it, and how you had me do it again and again and….”
“He wouldn’t believe you. He wouldn’t.”
“You don’t sound so sure, Debbie.” I started reading the part of the letter about the masked man again.
“Ok, ok, I get it,” Debbie interrupted, before lunging for the letter, which I held just out of reach. She whined, “God! How pathetic. I can’t believe you’re blackmailing me. I’m married. I just can’t have sex with you.”
(I wasn’t proud of that fact either. It made me re-think.)
“Ok, Debbie, just give me that do-over, and I…well, I won’t even ask for intercourse. I promise.” (It was a promise I didn’t know if I could keep.)
Debbie perked up. “No intercourse.”
“Nope, but don’t sound so victorious. We’re still going to play and do everything else. I’ll just keep my dick out of your pussy.” I moved over and brushed her bangs. “Right, just play out MY fantasy of a do-over, and things will be square with us. I’ll give you back your letter, and we can go on with our lives.”
Debbie asked several question as to my intent, but I remained stone-faced. She thought it over for a couple of minutes, and then she nodded sheepishly.
Gentlemen, start your engines!
———————————- Part 2
Debbie emerged from the bathroom about a half-an-hour later. I smiled, liking what I saw.
“I feel silly,” she whined.
I checked her out. She didn’t LOOK silly.
She was dressed in the outfit that I’d picked out for her. It reminded me of the one she wore the last time she shared my bed, except for a pair of black open-toed high heels to satisfy my fetish. (She tried to get away with some silly flip-flops.) Her outfit consisted merely of a pair of shiny pink shorts and a thin black top. She sulked when I handed her the outfit, but it was her clothing, and I reminded her that it would soon be on the floor anyways.
Now standing before me, the simple outfit looked sexier than I had remembered. She blushed under my scrutiny. I examined her nicely made-up face, another instruction she had followed well. She seemed amused that I cared so much about her hair and makeup, until I finished by telling her to use that lip-gloss that she had on at the wedding. (“Lots of it.”)
She smacked her lips (obviously reading my intent), while shifting her eyes to my crotch. “Why? It will just rub off on your, you know, anyways.”
“Maybe I want a souvenir.” I winked. “Because I’m planning on leaving you with a little something, something.”
I was laughing to myself, like a bad comedian, when she cleared her throat, breaking in on my thoughts. I moved her over to the far side of the bed and pulled up this fancy cedar chest and sat down. Her head swiveled. She was boxed in, and she knew it.
“Ok, lets get this over with,” she pouted.
I sat there and continued to look her over. I had waited a long time for this, and I was going to take my sweet-ass time.
Finally (as if to take us back in time), I snapped my fingers. “Well, Debbie, I see you’re back, and you want to spend the night in my bed.”
She sighed. (I wasn’t sure if she was going to play along.) “Yes, please, may I?”
“I don’t know. My bed’s pretty small and…well, I might need a little convincing.”
Debbie rolled her eyes. “What do you want?”
(She wasn’t doing a real good job of acting. I didn’t care much, because I had waited a long time to say this.) “Why don’t you show me your tits, for starters.”
“Tits.” Her hands flew up to her chest.
“Yeah, let me see those puppies.”
“C’mon, just let me spend the night, you know I don’t snore.”
(She didn’t.) “Let’s see…, I’ve seen you in a bikini, and some skimpy tops, but I’m looking forward to finally seeing the mystery that is your nipples.”
“M-mystery?” Debbie mumbled.
“Yeah, I’m pretty sure about the shape and size of your breasts, but the exhilarating part is the nipples. Like what color are they? How long and hard do they get? How sensitive? I still have no idea. It’s still a mystery.”
Debbie looked down at her chest. (It hit me that she probably hadn’t thought about her nipples as much as I had.)
“Lift that top up and reveal your mystery.”
Debbie’s head flew up. “Ah, maybe I could show you my ass instead.”
I chuckled. “Oh, I’m planning on seeing that, too, and more…. Now, show me your tits…FOR STARTERS.”
“Wait, time out. Just what else are we talking about?”
“Nice try Debbie, get going.”
She huffed and turned her head to the side and pulled up her top, just over her breasts. I gasped. There they were, after all these years. Her nipples were seductively pink. They were surrounded by brighter pink areolae. I licked my lips. Set against her creamy white skin, they were very erotic, and looked very suckable, but there would be time for that later.
“Now, lose the shorts.”
“Hey!” She whined, yanking ’em down. “You don’t have to be so fresh.” She threw them at me. I picked them up and made a show out of sniffing them. (I, at least, had no problem acting 18 again.)
She twirled (to show me her ass) and then posed, hands on hips in a show of bravado. My eyes took in every inch of her full frontal nudity before she tried to hide behind her hands.
“Ok, you’ve seen what I got.” She picked up a pillow and held it in front of her. “Do-over: done.”
I just shook my head with a sly smile. “Done? Not yet. Not hardly.”
She huffed. “But you saw me….”
“Not all of you.”
“What?” she gasped. “You Pervert!”
“That’s right. I want to see your pussy.”
“But you saw it.”
I laughed. “I saw your cute little landing strip, but I want to see where the plane parks.”
(Maybe, but I was having fun.) I ordered her over to the bed.
“Just think of me as a doctor.” Her story of her first visit to a gynecologist rang in my head. Especially about how embarrassed she was to have to put her feet up in those metal things and spread her thighs wide so her doctor could put his finger and various metal objects inside of her pussy. All for a man she just met. It almost made me go to medical school.
“You know I hate doctors.”
I nodded, knowingly. I watched a small tear roll down her cheek. It didn’t move me. I knew it wasn’t a tear of pain, but of humiliation. And I wanted more. I don’t know why I wanted it this way, but there was just something inside me. I mean, I knew all about her past, and yet I made her strip for me. (Like her step-mom did all those years.) And I knew she had a thing about doctors….
I snapped my fingers, and she slouched over to my side, dropping the pillow. I felt her hand brush the side of my hair. It was electric. Her womanly aroma danced into my senses. Out of the corner of my eye I could see her left nipple begging for attention. I turned my head slightly and took it between my lips. Debbie purred as I sucked it in. She pulled me tighter and continued to stoke my hair, her fingernails lightly scraping my scalp. “Yes, that feels good.” she moaned. “But the other one is jealous.”
I slid around (not that I need any encouragement) and took her other nipple into my mouth and sucked on it with vigor. She told me how good it felt. I felt my cock flutter and start to grow. I reached up and cupped both of her breasts, pulling them close so I could switch back and forth between nipples.
“See, you feel good, and you’re making me feel good,” she whispered, as I continued to suck on her nipples. “You don’t want to do bad things to me? (I shook my head.) “You want to do GOOD things.” (I nodded.) “I’ll be nice to you too, and do that thing you want, that every guy wants, with my mouth.” (My ears stood up.) “And you won’t cum in my mouth or on my face, will you? (I shook my head.) “Right! ‘Cuz that’s bad.” (I nodded.) “But you can cum on my breasts, I see how much you like them.” (I did.) “Ok, so let’s switch places and let Debbie make you feel good and then we are even, Stevie, OK? (I nodded.)
I stood up, and Debbie started kissing her way down my body until she was squatted down in front of me. She lightly brushed my crotch. “Looks like someone is good to go,” she snickered. That broke the spell. I reached down and pulled her to her feet and tossed her back onto the bed. She looked surprised.
“Nice try, Debbie.” I grinned, because she almost had me. “Seduction 101. It might have worked if I was still 18, but, let’s face it, we can’t go back in time.” I sat back down and patted the corner of the bed. “I’m a grown man now, and I know what I want and how I want it. So where were we? Oh, yes, you were about to show me your pussy.”
Debbie wasn’t happy and did some bitching, while I just kept patting the corner of the bed. Even though I didn’t say a word, she finally slid down to me and dropped her legs off the side of the bed.
I slid forward and spread her legs farther apart and pulled her towards me. Satisfied, I leaned in for a look at her shaved pussy. Her pussy lips were clearly visible and snuggled tightly together. (Jesus, just like I like’em.) I took some deep breaths before I gently rubbed along the edges of her pussy, circling my target. I sucked on my right index finger, making a show of it. Debbie saw, but looked away.
I ran the moist finger up and down through her pussy lips. (I wanted pink.) Not satisfied, I gathered some spit and released it on target. I used my spit to spread her pussy lips, fan like, until they stayed parted. (I had pink!)
I picked her legs up and bent them back, her thighs moving farther and farther apart, until she was fully displayed. She looked down at her new position and gasped. I reached out and began stroking the surfaces of each of her perfect pussy lips, while admiring their smooth, elastic texture. Once again I spread her lips way out. (It figured.) She had positively the most exquisite pussy I had ever seen. My eyes watered. (This was sleeping right next to me all those years!)
I blinked my eyes and focused. It was time to find out how she felt inside. I told her to “relax.” She exaggerated a sigh. I slipped my right index finger, ever so gently, into her hot little pussy. Slowly at first, I moved it in and out, letting her get used to the feeling, and then began using two fingers. Harder, deeper, faster…. Then my left thumb joined the fun and ran small circles around her very noticeable clit. Bit by bit, I threw in every trick I knew…and some I dreamed up on the spot. (There goes my medical license.)
When I got my first moan out of Debbie, I licked my lips, figuring it was time to move on. Her pussy looked great, and it felt great, so there was only one more thing to do. I threw her legs to the side and slid my hands under her ass to cup her cheeks. Then, while lifting up, I leaned forward and ran my tongue from the bottom to the top of her pussy.
“Oh no, no you don’t!” Debbie cried out.
“I do,” I said, before taking another lap.
Debbie put her hands over her face, but she didn’t move from her position. (Why would she?) I continued my munching. Once again, I used everything I knew and probably did some stuff just by accident. For a while there, I was just a wild, pussy-eating madman.
When she finally climaxed — or at least cried out like she did — she started begging for mercy. I stopped licking, but I wasn’t finished with her yet. I fished out the tube of lubrication that had been warming in my pocket. I slid her down to the end of the bed and pressed her legs back, way back. She looked concerned, but still a little hazy.
Warning her to stay in position, I grabbed the lubricant and squeezed some out onto my index finger, making sure she could see me do it. Then I ran my finger around her asshole. She gasped. I slowly started working my way inside. The grip was extremely tight. I added some more lubricant and went back to work. She recovered a bit and screamed out, “NO!” That was OK, but when she kicked me in the shoulder, I figured I’d crossed a line.
I wanted to apologize, but couldn’t find the words, so I grabbed her again and went back to eating her pussy. When I added a finger, she started to moan again. Then I slid my finger out of her pussy and slithered it into her asshole. She cried out (“Why?”), but didn’t kick me this time. I didn’t answer, but I did slow down…and finally stopped, taking one last look before climbing up onto her body. I held her face in my hands and pressed my lips to hers (our first kiss). She tried to break away (for obvious reasons), but I had a good hold and a quicker tongue. She finally relaxed and helped out, while I ground my hard crotch into hers.
I spent some time kissing her neck, and nibbling on her ears, before bouncing off the bed. I grabbed a pillow and dropped it on the floor in front of me.
It was time to get my dick sucked.
I summoned her by whistling and tapping my crotch. She burned, but slid off the bed and took her place on the pillow. I patted her on the head, which drew another dirty look. I used my thumb to trace her glossy lips, while trying to keep my composure. She started sucking on my thumb. This, and the realization that, after all these years, the lips that I had dreamed about would soon be wrapped around my cock, made me pick up the pace (before I came in my pants).
“Now, suck my cock like you should have done, way back when.” I slid my pants down and kicked them free.
She whimpered, but pulled my underwear down my thighs. I think she closed her eyes because she banged her face into my cock a few times before taking it into her lips. (Yes!) She swirled her tongue around and didn’t really move her head much. I was thinking that maybe she was out of practice because I was assuming she didn’t do this with her husband.
A handful of hair was all that was needed to get her going and for her sexy dark eyes to open. I fucked her face until she pulled back, begging me to let her suck. That’s what I wanted to hear. I folded my arms behind my back, pompously, and waited. Debbie did some muttering, but when she returned to my cock, she did better, though she still she wasn’t into it. (It hit me that the last blowjob I’d had was from a paid professional. It was great, but over too fast.) One good thing about this one was I was going to be able to last. I figured this would be my only one, so I was planning on making the most of it. Anytime I felt I was getting close, I’d make her stop and lick the shaft of my cock. (She flat out refused to lick my balls, but that’s never been my thing.)
When I knew I couldn’t take much more, I tossed her onto the bed. I flipped her over and dragged her to the bed’s edge. Then I had her reach back and grab her heels. She was now in position. She started to complain, but I shoved my cock back into her mouth. (I’d heard enough.) Fucking her face, I closed my eyes and resumed my day dreams. I changed her from one position to the next, each one designed for my pleasure. I finally had her back on the floor kneeling in front of me, held there by a handful of hair. I began stroking my cock. She was trying to pull away.
“Don’t come on my face!” she cried out, but it was too late. Her protest was met with flying streams of cum. (Now, I’m not exactly a human sprinkler system like Peter North, but I did make my mark.) I ran my cock along her lips, and she took me in, ever so briefly, before she got up and scampered into the bathroom, slamming the door shut. I immediately felt remorse. Normally, I wouldn’t have thought twice about it, but she was different in so many ways. And, like I said earlier, I also knew about her past.
My mind drifted back to THAT damn day….
It had started off pretty normally. I had gone over to Debbie’s house to see if she wanted to go to the Mall. But, as I was about to knock, I heard loud cheering from inside. Curiosity compelled me to peek into the living room. There were some thin drapes in my way, but I still could make out four men standing in a circle. I suddenly realized that there was a naked body lying on the coffee table beneath them.
“DEBBIE!” my mind screamed, but then I saw her off to one side, out of the corner of my eye. I found a better spot. I could see that Debbie, wearing a white bikini, was sitting in a chair…tied and gagged. I was about to rush in like some sort of hero when I saw her father’s face. (Oh, god!) He was one of the men.
The men flipped the woman over and made her grab her heels. They moved around the head of the woman, and they all appeared to be jerking their cocks. (They still had their pants on.) I couldn’t believe that a circle jerk was happening right next door, in the middle of the day. When the group finally broke up, Debbie was released from the chair. I kept a close eye on them now, but she wasn’t touched. However, she didn’t get off easy. Under her father’s belt swatting ordears, she had the job of cleaning up the woman’s face…with her tongue. It almost made me sick. (I never realized that it was her step-mom until later.)
After that day I came up with all kinds of plots to get Debbie out of there. I just had to. Then, on Halloween night, her father was killed in a car accident coming home from his favorite pub. The car was mangled so badly, and with his blood alcohol level, they never did check the brake lines. No, he was just another dead drunk driver….
I shook with the memory. I stood up and paced the floor. Debbie took her time returning from the bedroom. In fact, I wondered if she would at all, and several times I thought maybe I should leave.
Suddenly, the door swung open. “God, I can’t believe you did that to me.” Debbie marched into the room. “I’m not a whore. Give me that letter and get out.”
I handed her the papers, and she tore them up and tossed them away. “There, that takes care of that. I hope you had your fun.”
(I did, but I didn’t feel like I thought I would. The night hadn’t gone as planned.)
She sat down on the bed. “Well, what do you have to say for yourself?”
I didn’t want to, but I started spilling my guts, while pacing. “This is the only thing I know, that if you’d have chosen me, I would have treated you like a princess, because that’s what you were to me. Why do you think I never tried anything with you all those years? I knew something was screwed up at home, and I knew there was more to you then a killer body. So I was there for you. You know what that is? That’s what they call love, Debbie…not just lust. No, I loved you. I loved you so much. I wanted the sound of you breathing to put me to sleep, night after night, forever.” (I wonder if she would ever know the lengths I would go for a loved one.)
I moved over to the bed and lifted her chin up until our eyes met. “But maybe you’re right. Maybe lust is all I have left. I think things changed the night you decided to break a promise and fuck my cousin.”
She pulled away and dropped her head and murmured something.
(What was that?) I froze, finally managing to mumble, suavely, “Huh, Debbie?”
“I said, I’m sorry.”
“Sorry?” (It’s had been the one thing missing. She’d never said it, not once, in all these years.)
“Yeah, I-I-I was young, and things were messed up, but something about the way you loved me…it was scary. It was like if I didn’t get away soon, I knew I never would. No one’s ever looked at me like you did…do. I didn’t understand it. I’m sorry. I’m sorry.” Debbie burst into tears. It took me only seconds to do likewise. I sat down next to her and slowly took her into my arms.
We sat up and talked and talked, clearing the air. It was painfully clear how much she loved her husband and how happy they were. After two hours, I was pretty sure she’d made the right decision — for her, anyways. I finally figured it was time to leave. I leaned in and kissed her…for one last time.
“Take these,” Debbie said, picking up my mask and knife. “Go out and come back in, wearing this, and do whatever…as many times as it takes. Just get me out of your system. I can’t be your dream girl anymore. There is someone out there waiting for you. Life doesn’t end at 18.”
I was shocked. She slipped off her robe (giving me one more look) and slid into bed. I grabbed the stuff and walked out of the room. Taking a last look, I closed the door. I stood there for a minute, thinking. She was right. I had to get her out of my system, but I knew if I opened that door and went back in that I’d never do that. I dropped the mask and knife (they were her fantasy, anyway) and walked to the back door.
I sat for a time in my car, taking one last look at her house. It was a long look. After awhile, the lights came on in room after room. Debbie, I figured, looking for me. I shook my head, already wondering if I’d made another bad choice.
I took a deep breath. I had to stop using her as a crutch. I pulled out the well-worn photos that she and I had taken in that amusement park booth so many years ago. I gave them one more kiss. “Bye, Debbie, have a nice life. Be a good mom.”
I tore up the photos and tossed them out the window as I drove off in search of someone new, someone who would love me back.
It was time.
Thanks for taking the time to read my story. I’ll appreciate any feedback you think I deserve.
Edited by C. Lakewood