Loading...A courier brought the package that morning, my secretary had told me. I opened the express envelope to find a key card with the name of a high profile hotel near the airport. A room number and a time were written in permanent marker on the back scribbled next to her initials.
The appointment was for that day of course, not more than a few hours away. I’d had to make excuses and told my secretary rearrange my schedule. I wouldn’t miss this appointment. I’d been waiting for so long for her to come around. At that point she knew I would even blow off a board meeting to get in her pants. We’d spent too many nights in the last few years hanging on my office phone whispering desperate, deep, dark fantasies to each other while my wife slept obliviously two floors above. She’d become a habit, and worse a fixation.
But lately, I hadn’t called her at all. We had to slow down because of my wife. Now that the heat was off, I tried getting her to meet with me by email for two weeks but she were always too busy or something. Oh yeah, she knew I’d drop everything and come. I always came when she wanted to play a game.
I parked discreetly in the hotel’s lot to avoid the valet. I couldn’t have my name officially tied to a sordid affair. Although, I really got off on the time she’d tied me to whatever she’d wanted to. I made it to the suite evading help and dodging eye contact, acting like I knew where I was going.
I let myself into the room. There was a note sitting on the coffee table of the suite. “Steve, there is a suitcase in the bathroom. Put on everything in the case. Everything. Shave if you have to-no facial hair-no moustache, no beard. When you are finished, turn off all the lights and light the candles. Put on some music and wait for me. There are wine coolers in the refrigerator. Be on the last one when I get here. Do not drink the beer.”
What the hell!! I had to shave my moustache and drink wine coolers. Good god. I was going to have to make up some bullshit story for my wife to cover my bare upper lip. She was pushing it this time. And we both knew she was in the position to do it.
I checked out the fridge. There were three cartons of wine coolers. I started with a grape and headed for the bathroom. I had about an hour. The first cooler was very sweet, that I definitely remember. I was glad I hadn’t been able to break my lunch meeting. My idea of a good time was not twelve wine coolers on an empty stomach.
I hung up my suit and dress shirt. I opened the suitcase and rifled through it first. After pulling out some of the clothes, I was really starting to wonder what game she had in mind. I found the razor and shaving cream. Given the contents of the case, I considered myself lucky the razor wasn’t pink and plastic.
After loosing my moustache, I returned to the case. I pulled out the thigh high black stockings. I vaguely remembered telling her about wanting to wear hose once. This wouldn’t be the first time she’d gotten me drunk and had her way with me. I took a swig of the cooler and shrugged. I pulled a stocking up one leg and was instantly hard. I thought, “Whoa I need to slow down.” I had to reign this in already.
I pulled out a short black skirt next. I rolled my eyes wondering what the hell she’d been thinking. She was either really pissed at me or… or what? I finished the cooler and pulled the skirt up over my hips and briefs.
On a trip to grab another cooler I saw myself in the mirror. I was blown away. My cock jumped under my skirt. God, I liked how prissy I was starting to look. She must have known I would get off on that.
I think I grabbed a strawberry cooler that time. It was still hideously sweet but I stomached it. It wasn’t a far stretch from the Kool-Aid we used to drink as kids.
I dug into the case and found a bra with falsies attached in the cups. She was always so retentive— I wondered how long she’d devised a bra with fake tits already attached. I rolled my eyes at the thought. It might have been funny but I loved that detail orientation. It made her a great lover.
It took a hell of a struggle to get the bra on- I realized how much easier they are to remove than put on. Next I found a pair of panties at the bottom underneath a long blond wig. I haphazardly stuffed the wig on my head-my focus was all about the panties at that point. They were a silky black pair with a thong running up the back. The front just covered me. My cock throbbed as I danced out of my briefs and pulled the panties up. They held my cock with a constant silky pressure against my cock and the thong strap ran up my ass like a wedgie. A very sexy wedgie.
I shuffled around in the case to find a pair of shoes in there. I slipped on the black heels. They weren’t too high, but high enough to make me wobble. The wobble reminded me to keep the pace on my coolers. I went to the fridge to grab another. I think I had a pina colada cooler next. I realized then that she was one of those people who mix and match coolers at the store before buying them. I hate that.
There I was in the mirror again, standing there with my pina colada cooler. The wig was all-wrong. And well, the rest looked pretty wrong too. But it was right enough to have me straining against the panties. What was right was that I looked so… humiliating. God. My head was spinning and my cock was so heavy. I wondered if I should wack off before she got there. I decided I had better not and went back to finish getting ready. There wasn’t much left in the case. There was only a button down shirt and a bag of make-up.
I pulled my arms into the shirt and buttoned it over my straining breasts. It was cropped and barely covered my stomach. The buttons pulled across the front when I turned certain ways. I wondered if she had known when she’d packed how nicely my bra would pull across my chest?
I took the make-up over to the mirror and start pulling it out. Let’s see… the instructions said put everything on. I set it all out and looked at it. And then I decided I needed another wine cooler before I started. Margarita was next. I thought I must have been getting drunk because that one sounded like it might be alright. I caught my reflection in the mirror and feel a surge of power. It made my cock throb against the silk panties. I kind of strutted back to the bathroom. The power was so heady I forgot the wobble that almost toppled me earlier. I swayed my hips and rolled my shoulders across the room and nearly spilled my pina colada down my shirt. I sobered a bit. It would not be a good thing to fall and sprain something and have to explain that outfit to a paramedic.
When all was said and done, I must say that I didn’t do a bad job with the makeup. I’d watched the women in my life enough that I knew what goop went on what part of my face. It looked subtle except for the lipstick. The lipstick was whore red, glossy and tasted sweet. It was very striking against my blond wig. I realized what a bad job I had done on the wig and adjusted it, hiding the stray hairs. I blew myself a kiss. My lips were heavy, pouty and wet. I even wanted them.
Then I really wondered if maybe I really was getting drunk from the wine coolers. I had some serious beer-goggles– only without the beer. Coolers were really a girl drink. I checked the clock by the bed; it said 3:00. Where was she? She was supposed to be there.
I lit the candles. There are at least a dozen in there-each smelling of vanilla or flowery. I set them around the suite and turned off the lights. When I saw that I still had more coolers to go through, I was glad she was running late. I swiped a wild berry one and something lemon-lime and sat on the couch in the lounge area of the suite. I cringed at the lipstick I left on the bottle. I would have to keep re-doing it. I wanted her to see what a good job I’d done. I wanted her to want my mouth like I had.
I finished another cooler and thought about masturbating again. I walked over to the mirror and watched myself. I turned one way and then another and swayed my hips a bit and remembered I was supposed to play some music.
Thankful for something to do, I found a station on the hotel TV channels whose music wasn’t too terrible, soft rock and mushy. I am sure that she intended me to pick that for this game.
I worked on my cooler and glanced at the clock.
She was almost 45 minutes late when I reached for the last half of my last pack of coolers. I was starting to get mad. And worse I was mad and drunk. Surely she would show up. I thought there was no way she could stand me up after she went to all this trouble. I relaxed a little at that. Was there a ballgame today? There might be. Traffic was always hell down by the airport on game days. I thought to myself as I finished the coolers from that pack that I would drink her beer since she was late.
But I didn’t. I wanted to see how the whole thing would play out. I had to check my makeup three times and pee twice before there was finally a knock at the door. I got to the door on wobbly legs and peered through the peephole. There she was… only she looked different.
I opened the door and said, “Where have you been?”
She looked down the corridor one way and then another to see if anyone had seen me. She tossed her head back and laughed at me. I realized how vulnerable I’d made myself and waved her into the room.
She was beautiful-only she’d cut her hair. “Your hair-it’s short.”
She smiled… “Yeah baby, and yours is long.”
I waved my hand. “But…”
She walked in and shut the door behind her. She turned to me and reached up and kissed me. I bent down and began to get into it.
She pulled away… “You got a beer for me babe?”
” You are late.”
She shrugged. “Something came up. Get me a beer. I want to watch you walk, you sexy thing.”
She pulled her leather jacket off and tossed it on the bed. She sat down at the end of the couch. I brought over two beers. She took both and said, “Where’s yours?”
I started to laugh until I saw her face. It was completely serious.
“You don’t like beer, sweetheart. Go and get one of those coolers you like so much and come sit next to me. And wiggle your ass a little more on the way over.”
I did what she said down to the wiggle and then sank down in the center of the couch next to her drinking another cooler. She stared at my legs spread apart in front of me. “Sit like a lady sweetheart. Don’t be a slob.” She smiled into her beer bottle. I crossed my legs and looked at her.
“You look beautiful today darlin’.” She put her arm along the back of the couch behind me. I smiled and said thank you. I decided I would play along.
“You look great in skirts.” She leaned into me.
I smiled a little, “Thanks.”
She put her beer down and turned my face to her and kissed me. We kissed and started tonguing each other. I started getting really hot. Her lips were on my neck and then nipping my earlobe. Her hand cupped my breast. Her words were in my ear, “You’re gonna let me finally go all the way, right baby?”
I groaned, ” Oh yeah.”
She looked me in the eyes and smiled sweetly, “Really baby, you’re gonna let me go all the way?”
I grinned. “Really.”
She kissed me hard and pushed me on to my back on the couch cushions. She leaned over on top of me, shifting carefully. “Am I too heavy?” I laughed and said no. The role reversal on top of the alcohol was making me feel silly. I stretched out underneath her with our legs twined together.
She was kissing me thoroughly with a lot of tongue as she unbuttoned my shirt and palmed my breasts. I was on the verge of laughing when she dipped her head and pulled the bra cup and falsie down. Her teeth grazed my nipple. She latched a hold of it and flicked her tongue back and forth. My hips bucked her.
“You like that huh? You like to have your titties played with?” Her grin was evil.
I laughed and nodded. She switched and went to the other breast. And it made me crazy. She asked me, “Now is that first or second base?”
My mind was a little fuzzy as I thought it out before I answered, “First, I think.”
“Hmmm.” She smiled and her hand crept up my thigh and under my skirt. She palmed by crotch, outlining my cock and cupping my balls. She slipped her hand to the top of my panties and down them rubbing the top of my cock, circling it, stroking the head with her thumb.
“Is this second?” Her voice was soft and serious.
I laughed. “Yeah, I think so.”
She pulled her hand out and sucked on her finger. Her eyes were on mine. Her hand went back under my skirt.
“Spread your legs.” I did and her finger pushed and prodded the thong of my panties aside. She watched me as she worked her middle finger into my ass to at least the second knuckle.
I dug the heels of the shoes into the couch. Once, she’d put a slim little vibrator in my ass and I fucked her ass as she lay across the hood my wife’s BMer in the corner of a parking garage where my wife worked. She said the vibe balanced the game. I just thought it was something I’d wanted to do again. She knew this. We always talked about our games when we finished each one-fine-tuning what we got off on. We griped about what we didn’t like-especially if the other one was into it. Those little acts could be used for bargaining power for the upper hand in the next round.
She kissed me once and then again deeply. Then, she started to finger my ass, pumping and probing deeply. “So do you think this is third base, then?”
I moaned a little. “Ummm. I’d say.”
I was starting to get tired of the games pace. My cock was straining against the waistband of the panties and I wanted to be inside her.
“I want to fuck you. Soon. Now.” I said as I pulled her closer to me.
She raised her eyebrows and wriggled her finger deep in my ass and then pulled it away. I was a little sorry for it to go. “That’s good. Cuz Darlin’ I can’t wait to fuck you.” She shook off my arm and pulled my hand to her crotch.
I gasped when I felt a bulge under her baggy jeans. I wondered what the hell she has under there but managed to get out all of “What…?”
“Yeah-I can’t wait to go all the way with you baby.”
Her hand left mine and slipped back under my skirt. Her middle finger crept under my balls, between my cheeks to my asshole and traced around in feathery circles. “You said we could go all the way…”
As my mind started to grasp what she ultimately wanted, she pushed her finger into my ass. Her thumb rubbed the top of the base of my cock. She alternately stroked the base of my cock and finger fucked me with deliberate sharp flicks of her wrist. I moaned and spread my legs a little to allow her room. She added a finger in response and started to reach a rhythm. She started in with words to match and began to negotiate my ass in another way.
“I… won’t…. tell.. a… soul,” she plunged her fingers into my ass with each word and pulled out with each pause, running her thumb up my cock alternately.
“It… won’t…. hurt… I… promise,” she was starting to talk and finger me faster.
“It’ll… feel… gooooood,” she wiggled her fingers in my ass as she stretched out the word good.
I was panting by the time she said, “You… will… love… it”
“You…won’t…get… pregnant,” she laughed then.
“C’mon darlin.’ You said you would. I know you’re not a prick tease.”
I couldn’t help but laugh at her. And unfortunately, this she took as yes.
She pulled her hand from under my skirt and stood up. She led me to the bedroom and the bad. I still hadn’t said yes. But she wasn’t waiting for an answer. It was part of the game. I could stop if I wanted. I could leave if I wanted too. But I was so scared and nervous and turned on by the thought of what she was going to do to me.
Would it hurt? If I left, I might never know what it would be like to be fucked in the ass by a woman. She pushed my shirt off my shoulders and pulled my skirt down over my hips. She told me to sit on the bed still wearing my panties and bra, and stockings. She bent and kissed me deeply, and reached around and unhooked my bra. She slipped it off my shoulders and tossed it aside.
She took off her shirt and kicked off her shoes. She slipped out of her bra. I marveled at how fast she could manage that. She stepped in front of me and unbuttoned her jeans. She let them fall down to reveal what I’d felt under them. She’d skipped the underwear for a strap-on dildo. I was eye to eye with a cock that was bigger than mine was. And she knew it. It was at least nine inches long and was also visibly thicker than mine. I looked up at her really unsure for the first time about what we were doing together that afternoon.
She smiled. And pressed her hand on the back of my head in the universal unspoken signal for “suck my dick.” I leaned forward and took the tip of it in my mouth. I had never sucked a dick before. She sighed.
“God you look hot doing that.” Her hands were on my head and mine her on her hips. We guided each other as she fucked my mouth.
“Hmm. I wish you could see this. Cock-sucking looks good on you.” I must have really looked good for her to break with character. I slipped a finger down between her legs in hopes that I could finger her. I felt that the strapon had a backside that was already imbedded in her.
She must have realized my break in character because she pulled away. She told me to lie down in middle of the bed on my stomach. I thought this was it. She was mad and was going to do it then. She ordered me to hand her one of the pillows and put my head on the others at the headboard of the bed. I felt her nudge my hips and I lifted them and she stuffed the pillow under my hips, raising my ass in the air. She crawled up behind me and peeled my panties down past my knees.
“Spread your legs,” she said as she nudged at them. I did and she licked my inner thigh from the stocking edge up to my balls on one side and then did the same on my other leg. In unconscious response, I spread my legs even further. She settled on the bed between my spread-eagled legs and started with by balls, sucking them into her mouth. She flat tongued them in long strokes up to my ass. She pulled the cheeks of my ass apart and licked in long strokes up from my balls to my asshole. She rimmed the circle of my asshole slowly. I was panting by then, whimpering. She broke the rim and poked her tongue gingerly into my ass. I strained to open myself to her. At the opening, she tongued me fiercely. And then, she started to finger me. I felt her body shift.
I turned my head to see her reach for her jeans. She dribbled cold fluid along my crack and into my ass. She worked the fluid into my ass and gave another skirt into my ass for good measure. She pumped her finger in and out and around. She squirted a little more here or there. I wasn’t sure about the rest of her campaign promises, in particular the one that it wouldn’t hurt. But by that point, I wanted her to go all the way. Fuck it– if I got pregnant. Anything that started with a deep oil message was something I was into… even if it was in my ass.
She crawled up beside me and told me to roll over. I thought I would cry. I actually wanted her to fuck my ass at this point. I think I had actually wanted it for quite some time.
She kissed me and laid on top of me cock to cock with her hips and legs between my legs. She told me to lift my ass up and she shoved a pillow higher under my lower back. She pulled my knees up and held my stocking clad legs at the back of my knees, high and wide. I got stage fright when she pressed the tip of her strap-on to my ass and pushed. My ass shut her out completely. I watched her looking intently at me as she shoved her way in regardless to what my tight little ass had in mind. “It’ll be easier if you work with me Darlin’,”
“Relax…push out.” She pressed on.
I was squeezed tight. My head pushed back in the pillows. “I know. I know…” I did know. I’d coached her when I fucked her ass for the first time.
I pushed open a little to her and groaned from somewhere deep inside because her cock immediately pushed through.
“Oh yeah. That’s it. Keep pushing out.” She was staring down into my eyes.
This was wider than anything we’d tried before when we’d played. And it was much longer. Oh god, was it longer. It just kept coming. And she was smiling slightly; her eyes were dilated, as her cock pushed deeper and deeper. I was spread wide and she kept coming. I tried to pull my hips back a little but she kept invading me. When she broke past my ass’s resistance, she was everywhere inside me. My head turned back and forth as if to shake her loose from my mind. By that time I knew there was no shaking her loose from my ass, she felt too deeply imbedded.
“Now I really wish you could see this. I’m not even all the way in yet.” I cried out at this point and she laughed a little.
“And you are spread so tight around my cock.” She was fascinated by my asshole and touched it with her fingers gingerly.
“So tell me how it feels to lose your virginity, sweetheart.”
I moaned.
“What was that?” she goaded.
“Ugh… ugh… it’s so huge. This is too much,” I whimpered.
“Awww. I bet you say that to all the guys.” When she pulled out a little, I relaxed and breathed. I hadn’t even realized I’d been holding my breath. She ran her finger around the rim where my ass stretched around the cock. ” Do you like it?”
I started to answer. I knew what she was doing. She was giving me time to get used to her. I nodded and answered, “Yesss..”
She started pushing in further again, I responded, “Aahhhhh… oh god.”
“Do you still like it?” She continued to sink the strap-on deeper into me while she talked.
“Yeah..”
“Yeah what?” She rocked in and out slowly.
“Yeah I like it.” I said it in a rush.
She stopped moving. “Beg me to fuck you, Steve. Beg me to fuck your ass.”
“Fuck me.”
“Fuck you where?”
“Fuck my ass.”
She started to pump my ass in a slow even fuck.
“What’s the magic word, Steve?”
I shook my head and she stopped.
“Oh.. Oh please, fuck my ass.”
She smiled, “Ah’ight then.”
She wrapped my legs around her waist and moved above me. Her arms bent slightly at the elbow, holding her weight over me. Her arms were really toned. Had she started working out since we’d last played?
She held my eyes with hers as her hips rocked the strap-on in and out of my ass. I glanced down to her breasts swaying over me and reached up to touch them, rolling the nipples between my fingers and thumbs. I ran my hands down her back to her ass clenched in concentration. I pulled her deeper into me. I moaned but she grinned and followed my lead. She was finally flush in my ass and started to grind it in small circles. Whatever was on the other side of the strap-on started to work on her now that she was in me full to the hilt. She stretched her head back to the ceiling and closed her eyes. I touched her neck, graceful and bowed. She looked down at me making intense eye contact as she fucked me very, short, deep thrusts.
She changed rhythm and pulled most all the way out, and then I pulled her back in with my hands on her hips. We did this over and over again. Eventually, she fell down onto my chest and smashed her breasts against me. Her arms wrapped under mine and gripped my shoulders from behind for leverage. I held her in the circle of my arms and wrapped my legs around her. For awhile she gently and rhythmically stroked in and out, her face turned and her cheek resting on my chest. The moment was almost sweet… I felt like she’d completely possessed my body. I found her rhythm and could match her. My cock burned between us. The friction of her stomach moving over it kept a bead of cum at its tip. It reminded me of a dry fuck when I was fifteen.
Then she looked up straight up from my chest and tightened the grip she had on my shoulders. She started to speed up and was soon driving into me, and grinding when she plunged really deeply. She was too fast and too sporadic for me to match her. When she hit a good deep stroke, she stayed there pumped in tight fast circles. She was frigging her clit with backside of the strap-on while the friction between our bodies stroked the head of my cock. My mind was racing to catch up with her. She bury the strap-on and grind and then pull way out and slam it home over and over. When she came, the combination of her moans and her face reflecting her orgasm shocked me. This shock and her sharp thrusts, and the friction on my cock sent me over the edge. I started to come. I hugged her hips into me with my legs when everything in me centered on the cock in my ass. My fists clenched tight against the bed forcing me to arch my back. And my ass clenched repeatedly like a vise around her strap-on for every spasm of cum I spurt between our stomachs.
She lay on top of me for quite awhile. My breathing slowed eventually and I stroked her hair. The tenderness of the gesture brought her around. She pushed herself up and pulled out of me. I moaned a little when she did. It hurt and it didn’t. After I came, her strap-on felt so hard and foreign up my ass. But when she pulled out, she left a lonesome, empty spot where the strap-on had been. She bent and kissed my lips. I wondered wildly what my lipstick looked like.
Off she went to the bathroom. That was usual for her. I closed my eyes and tried not to think about where our game had gone. She was playing again, at least and we’d talk about it after. We generally did.
Except when I opened my eyes, she was back in her street clothes. I propped myself up on an elbow and said, “What’s up? Where are you going?”
“You know how it is. I have to get going. Work, you know.” She was at the door.
“But…” I started. We always talked about the game after we finished. It was her favorite part. And fuck it, she was really blowing my afterglow.
“But….?” She led me to finish.
“Can I see you next week?” I was brought up a little short.
She paused on the other side of the door to the outer part of the suite. “Mmmm. I don’t know. I’m going to be pretty busy. Meetings, work. And don’t forget that out of town conference. You know how it is.”
There was an awkward silence in the room.
“Tell ya what…” she started and blew me a kiss. Her last words before the heavy hotel door rushed shut behind her, hung in the air “I’ll call ya.”