Sheila and I started dating after a year of working together. I was an executive in the company and she was a relatively new analyst so we had to keep our relationship secret. However, we both loved public play and the risk of it all. A lot of buildup at work led to a wild night of sex and a threesome the following day. This is how it all unfolded.
Sales Meeting - Friday, 9:30am
Our weekly sales meeting had just concluded. She stayed to speak with me after. “I have a few questions,” she said. I laughed to myself at the generic nature of her ‘request.’ I ran my finger over her collarbone and down her spine. I felt her shiver as my finger reached the top of her ass. I could feel her nervousness. Our all-glass conference rooms had just a two-foot opaque frosting wrapped around the four corners. And unlike outside of the office, inside of the office she knew we had to be absolutely discreet. She started to ask me a question.
I interrupted her before she could finish. “No, you are going to keep them on.” I lowered the zipper on her pencil skirt. My finger continued in between the crack of her ass, over her asshole. I held my finger still in between the soft ridges of her cunt, stretched over her clit. “Delectable,” I told her as I held my finger at my nose. “You’re drenched and it’s barely 10am.”
I knew the thought of being caught in the office was overwhelming for her. It was for me as well. We worked at a large software-as-a-service company with a very conservative work culture. Grey suits, oxford dress shirts and pencil skirts were unofficial uniforms. Our office personas were necessarily the opposite of our personal personas.
When she wasn’t working or with me, she was likely working out. Obsessed with her health, her figure was proof—5’4”, 105 pounds., long brown hair, piercing hazel eyes, retroussé C-cup breasts, tight sculpted core, and a perfectly plump ass—physically she had it all. Most of the people in our personal lives had seen it. Out of work, she liked to show off. The tight knots on her homemade crop-top white tee-shirts ended between her breasts. The fabric on her body-conscious dresses barely touched her thighs. The silky slips she wore to dinners and occasions were often sheer, always thin and very loose. If she leaned too far forward an areola would peek out. When you walked by her, you wouldn’t be blamed for gazing at the profile of her bare breasts. She loved showing off. And I loved showing her off.
All Company Meeting - Friday at 12pm
I had my assistant interoffice a small box and note to her. I knew the risk of using interoffice mail would drive her insane.
Something to help you focus today. See you at Noon, the note read.
She had to present at the all-hands company meeting. While an important professional moment, this was also an opportunity to ignite her eroticism.
You’re so bad, she texted me, followed by a selfie of her wearing her new anal plug.
I texted her back, Good girl.
We met at the coatroom after her presentation. She said she had to remind herself not to grind on her chair onstage. I told her she did well, though I did notice some fidgeting. She smiled. I left after two of our co-workers walked into the coatroom.
Elevator Lobby - Friday at 6pm
We left the office early. She had a party to host that evening. We met at the elevator banks at 6pm. Moments before the elevator door closed, I tapped her cunt. Timed as I had, I knew no one would see. But, she didn’t know that and she certainly didn’t expect it. Her shame and disgust were washed over by excitement. Her cheeks reddened, her body trembled. Her eyes slowly closed before opening back again. Now teary-eyed, she stared back.
I instructed her, “Take off your thong. Ball it up. Place it back in your pussy.”
She didn’t break eye contact with me as she followed my instructions. Her black heels gently rose over the thin fabric of her thong. She placed her panties all the way up her pussy just before the elevator door reopened.
Black Car Service - Friday after 6pm
As we walked to the black sedan I noticed a single stream of wetness slowly dripping down her thigh. Once inside, I slowly tightened my grasp of her hand as I leaned over and asked her, “What type of girl gets so soaking wet that she is dripping down her thigh even while her panties are stuffed in her cunt?”
She stared back at me. I was struck by how warm her thigh was as my middle finger strode over the top of her inner thigh and across the interior ridges of her groin. I felt her clit vibrate when my middle finger met it.
I pressed slowly before pulling away and whispered in her ear, “The least you can do is clean up after yourself.” I fed her cunt juices back to her. She sucked dotingly, never breaking her gaze as we pulled off.
The yellow and purple hues of sunset filled up the car as we turned down Second Avenue. I felt her hand tighten over mine as we approached the front door of her apartment building. “I’ve got it,” I told the driver before releasing her grasp.
I could feel my bulge shake as I approached her car door and even grew a bit anxious when I saw its reflection in the car window. When I opened her door, she stared directly at my crotch and slowly raised her eyes to meet mine. She grasped my hand as she exited the black car.
We stopped to get her mail. The elevator was out of service and we had to walk up six flights of stairs. She closed her mailbox and held her keys and mail with one hand.
She looked directly into my eyes and stretched her index finger across a protruding vein extending down my penis. She followed it through my entire length. The thin fabric of my blue slacks was no match for the physical heat of our mutual lusts. I squeezed inside so my bulge would pulsate, my way of saying hello. She smirked as she squeezed my crotch slowly. She loosened her grip and tightened over and over again. I could feel my balls squeeze outside of her fingers.
She leaned forward and finally removed her grasp. Even while pushing her body off of mine, I could feel the electricity of her suppleness. She ran up the stairs ahead of me to show me the result of all the day’s teasing.
“You didn’t answer my question,” I whispered to her. I bit and nibbled on her earlobe while I leaned my warm bulge against her skirt’s thin fabric. “I asked you what type of girl leaks cunt juices down her leg?” I released my grasp of her ass and moved my forearm between her legs.
She stopped trying to turn the key as my forearm slipped back and forth across her cunt. Her soaking wet lips glided across the veins of my forearm, tickling ridges that had gone previously unnoticed. I grazed her belly as I slid my forearm out. I groped her ass as her eyes reopened. She regained her awareness and opened the apartment door.
Sheila’s Apartment - Friday Early Evening
Her apartment building was unique. The eight-story building, zoned for commercial real-estate, held eight lofts. Her 1,800-square-foot loft held three bedrooms, one bathroom and a very large living room. This is why she and her roommates tended to hold gatherings there. The ceiling was remarkably tall at fourteen feet and the living room boasted floor-to-ceiling windows facing arguably the busiest street in Manhattan. Her bedroom was immediately behind the living room, so close that it looked like it could have just been an extension of the living room. Her roommates’ bedrooms were both on the other side of the loft with an adjoining bathroom.
“Ariela? Johanna?” she shouted as she opened the door. She expected her roommates would be home since they were in charge of setting up for the party that was just an hour away from starting.
As she placed her keys on the dining room table, she received a text. She turned to me and said that they would be home in thirty minutes while she rubbed her thigh over my bulge.
I reached behind her and rotated her plug. As we kissed, I opened my hand and cupped her ass and cunt at the same time. I placed two fingers inside her pussy and pulled her thong out. I turned her around and placed the thong in her mouth while I slowly milked her pussy with my fingers. I could feel her wetness on the palm of my hand, dripping down my wrist and forearm. I pulled her breast out and teased her nipple, licking around her areola, sucking her nipple, then sucking her areola until her entire breast was in my mouth. As I sucked her breast, I finger fucked her deeper. I could feel her body tremble and knew she was close to cumming. She used her hands to hold her body weight up on the table while she panted.
Just as she was about to cum I pulled my fingers out and spanked her cunt. “No, not yet.” I continued, “You have such a greedy little cunt.”
She nodded knowingly. I placed my fingers back in and pumped them faster. “Fuck, I need it,” she pleaded. “Please,” she begged as she turned to face me and unbuckled my pants. I lifted her up and laid her on the table. I held her down while I tapped her pussy with my heavy cock. “Please,” she begged.
I took the head of my dick and parted her pussy lips. She was absolutely soaking. I moved my head clockwise slowly while I squeezed her nipples. I circled her cunt faster, never pushing further than the head of my cock. I could hear the air bubbles from her cunt juices pop as she gasped. I changed direction, moving the head up and down, then left and right, and up and down over and over again until I finally pulled away. She squirted all over the table onto the floor.
When I lifted my head up, her roommate Johanna was standing there staring. Sheila turned her head around to see her roommate. The silence seemed to last forever until Johanna broke it. “Wow,” she said as she walked back into her room and closed the door.
I went back into Sheila’s room while she went to Johanna’s to smooth things over. Sheila came back while I was changing out of my suit.
“She’s fine,” she said.
I told her that I was sorry, that I didn’t think anyone was home. Sheila hadn’t expected Johanna to be home either, but said she thought she “enjoyed the show.”
Sheila changed into a very short, very thin silk dress. As usual, she didn’t wear a bra or panties. As she turned to leave the room, I asked her where she was going. She called me silly and said she was going to set up for the party.
We heard the apartment door open. Her other roommate was finally home. I grabbed her arm and told her that it sounds like Johanna “has help now.” I pulled her back toward me. “I’m not done with you yet,” I told her while turning her around and pushing her against her dresser. I wrapped my hand around her throat while I slowly pulled her plug out and back in again.
She gasped and let out a few “fucks” while I fucked her ass. She noticed the curtains were drawn and onlookers could easily see. She looked back at me and whispered that her roommates were going to hear.
“What is the answer to my question?” I whispered in her ear while moving her plug in and out of her ass.
She muttered something inaudibly.
I pushed the plug all the way in her ass before placing three fingers in her pussy. “What kind of girl drips down her leg while her panties are stuffed in her cunt?”
She moaned and panted, but couldn’t gather her words.
“A dirty little bitch,” I whispered back to her as I finger fucked her cunt faster. I covered her mouth when she started to orgasm.
I got on my knees and took her plug out. I tongued her asshole while she rubbed her pussy on my chin. I sucked on her clit and made out with her cunt. She moved her hips back and forth, grinding her cunt over my cheeks, my nose, my lips.
She pushed me off and turned around. She placed two hands on the back of my head and told me to lick. And so I did, licking her from her asshole through her lips up to her clit. She moaned. She pulled my head more forcefully and held it still, using my face to fuck her cunt on. She climaxed with my tongue in her pussy, my nose against her clit.
We could hear more people outside the room. A few more of her friends had arrived. Neither of us cared. We kissed deeply with her wetness dripping off of my chin.
I grasped her throat, looked her in her eyes and told her to get on all fours. She obliged. She dropped to the floor, placed her palms and knees on the ground, faced the window and rested her head on her mattress. We noticed someone across the street. She began to say something to me about it but stopped as she felt me mount her. My thighs hovered above her ass as I reached forward and pulled her hair back.
While tapping her pussy with my heavy cock, I whispered to her, “Now, I am going to fuck you like a bitch.”
I placed the tip of my cock inside of her and she gasped. I pushed a few more inches inside and very slowly thrust in and out of her. Her pussy was drooling. She was panting. A few more inches inside and her pussy squealed. A few more inches and she screamed.
“Shhhh, you have company,” I told her. I moved my hand from her head to her mouth as I pushed a few more inches inside of her. Her screams muffled by my hand, I pushed a few more inches inside of her until I was fully inside. I fucked her slow and deep. My balls tapped against her drooling cunt with every thrust. I growled, moved my hand from her mouth and pulled her hair back again while I fucked her like a bitch in heat.
She bit the sheets on her mattress. I pumped and pumped until I unloaded inside of her. I turned her head around and told her to look at all of her cum on my dick, that it didn’t belong there and needed to be back in her belly.
She knew what this meant. She turned around, rested her back against her bed, opened her mouth wide and stuck her tongue out.
“Good girl,” I told her while I grabbed the back of her head and fucked her throat. After unloading again in her mouth, we both gasped and finally lay in the bed for a well-earned rest.
Sheila’s Apartment - Friday Night During the Party
We got plenty of stares when we finally re-joined the party. It probably didn’t help that Sheila’s nipples were on display all night. Her nude silk dress was loose, sheer, and very short. You could see her breasts shake with every step, every laugh, every movement of her body.
Sheila certainly was not the only stunner that night. Johanna was wearing a short mini-skirt that hugged her hips. Her ass was spilling out the bottom. Her cutoff t-shirt ended slightly above the bottom of her breasts, showing off just enough to drive me insane. Her well-toned core looked absolutely delicious.
I was glad that seeing us earlier didn’t set her off and ruin the party. I would come to find out that it did spark something else inside of her. A few times that night while walking past me, she “accidentally” moved her ass in my crotch and looked up at me with her big green eyes, smiling. The last time she did, she said, “Excuse me, big boy,” and dragged her hand over my bulge. I looked back at her. Now, standing next to Sheila, she laughed and stared at me before looking away again. She was always friendly but now was outright flirtatious.
The party was a success and after we cleaned up, Sheila, Ariela, Johanna, James and I kicked back to smoke a well-deserved joint. When James went into Johanna’s room to roll it, Johanna decided to use my lap as a pillow. He wasn’t happy about that. They argued in Johanna’s room while the three of us smoked the joint.
In James’ defense, Johanna was also a knockout—5’7”, toned body, gorgeous breasts, a plump ass and eyes that could convince you of anything—you would be insane not to want her. But, he wasn’t ready for her and that was the problem.
Sheila’s Apartment - Saturday Morning
The next morning, Sheila and I fucked in the shower. When we went in the shower, Johanna’s bedroom door (which was adjoined to the shower) was closed, but when we got out of the shower it was opened slightly. I didn’t think much of it and went back to Sheila’s room to change. Sheila put on a sleeveless cutoff t-shirt that showed off her breasts and abdomen and a high-cut G-string thong. While she was leaving the room I asked her if that was all she was wearing.
She giggled and said, “Come out in whatever; it doesn’t matter.”
After sending out a few emails I went to the living room in boxer-briefs to see how she was doing. She was laughing with Johanna in the kitchen. Johanna was barely wearing anything. She had on a loose, short sleeveless mesh shirt, no bra and a thong. I was taken aback because this was the first time I had seen her like that.
I teased them, “You two are always giggling.” They just looked at me and laughed more. I shook my head and sat on the couch. “Where’s Ariela?” I asked.
“Clinicals,” Sheila replied.
I asked Johanna if she was okay after her argument with James last night. She said that she was fine, but he was too jealous and she couldn’t stand it. I told her I understood that and that jealousy wasn’t healthy in a relationship. She said that he wasn’t even worth the headache. Sheila quickly agreed.
Then out of nowhere, she said, “He doesn’t even make me cum.”
I was shocked that she just came out and said that. Before that morning, we all hadn’t been nearly this open with each other, and there we were sitting in the middle of their apartment nearly naked, talking openly about her sex life. I went to the refrigerator to grab a water and hide the surprise on my face.
Sheila told Johanna that was “fucking tragic.” After agreeing, Johanna said that the hardest she climaxed in months was this morning while listening to us fuck in the shower.
I almost spat my water out. I was shocked. Apparently, I was the only one because Sheila shouted that she “knew it” and called Johanna a “sneaky bitch” while laughing.
Sheila’s nipples hardened while Johanna continued, “I mean, can you blame me?” She blushed and said that she couldn’t “unsee” what she saw yesterday evening and couldn’t get it out of her mind. Sheila started playing with Johanna’s hair.
“Well,” after pausing, Sheila continued, “maybe.”
She moved her fingers down from Johanna’s hair, tracing her collarbone, over her breast and down to her nipple. Her finger circled Johanna’s areola.
She continued, “Maybe you want to try him?”
I have had women objectify me before, but the way she posed the question shocked me. She posed the question as if I didn’t have a choice or as if she already knew that I was willing.
She looked at me and said, “Come here.”
I moved next to Sheila. She kept one hand on Johanna’s nipple and moved the other to the bulge in my boxer briefs. She grasped the base of my cock through my underwear as she looked Johanna in the eyes.
“I’m not jealous. I won’t mind,” she said.
Johanna was flushed with excitement and nervousness. And to be honest, so was I. On top of the present circumstance, I was intolerably horny because of the day prior.
Johanna asked Sheila if she was sure. Sheila responded by kissing her while pinching her nipple. When she pulled away, she reassured Johanna again, “I’m positive.”
Sheila pulled me by the base of my cock to move towards Johanna. They kissed again. I kissed Johanna and then kissed Sheila, looking her in her eyes as I pulled away to make sure she was certain. She nodded.
So I moved my attention back to Johanna. My hands roamed her body. She was a different version of perfection. Her skin, her scent, the valleys and arcs in her body were intoxicating. I moved my fingers all over her ridges, between her breasts, over her areolas, down the sides of her ribs, over her belly, tracing the outer regions of her cunt.
Sheila and Johanna kissed each other while I pulled Johanna’s thong aside. She was drenched. I traced her clit, her lips, the outside of her asshole and back again. Sheila moved from Johanna’s lips to sucking her nipple while I teased her cunt.
Johanna dropped her head back to enjoy the sensations when her phone rang. James was downstairs. She hit the red phone icon, sending him to voicemail.
I pushed my ring finger and middle finger in her cunt. Fuck, she felt amazing. I circled around, clockwise then counterclockwise, then extending, bending, and extending my fingers again in her cunt to tickle her clit while I pulled her wetness out of her. She panted, lost breath and continued panting.
Sheila moved over to her other breast, back to her mouth, back to her breast. She moved behind me and lowered my boxer briefs and whispered in my ear, “Fuck her good.” It all felt unreal.
I lifted Johanna up and laid her on the same dining room table I fucked Sheila on the evening before. She looked at Sheila. “Fuck,” she said while she laughed.
Her phone rang again. She ignored it. Sheila grabbed my cock from behind and spanked Johanna’s cunt with it. She whispered filthy things that I can only half remember at this point. She used my cock to play with her holes, moving it from her ass to her pussy and back again. When she released, she sucked and bit my neck before telling me to “fuck her good” again.
I obliged and teased Johanna’s cunt. Just the head inside of her rhythmically, clockwise, counterclockwise, up and down, left and right, over and over. She was leaking out.
Her phone rang again. She let it ring this time while she leaked down her thighs. She yelled “Fuck!” as she climaxed. Her phone rang again. She said James was either on his way or already downstairs.
Sheila said something like “fuck him” and grabbed my hips, telling me to fuck her. I obliged and pushed inside of her slowly. Her moans picked up speed. With every thrust, her cunt squeaked.
Then, a few text alert sounds. I ignored them and kept pumping her. Sheila moved from behind me to standing over Johanna. She kissed her and sucked on her nipples while I fucked her. Her body trembled as she climaxed again. I pulled out, licked then finger fucked her cunt until she squirted all over the table and floor. I went back in again and fucked her faster this time.
A few minutes into our second round, a few knocks rapped the door. Sheila muffled Johanna’s screams before removing her hand.
Johanna whispered, “It's James.”
Sheila smiled and covered her mouth again while I continued fucking her. She came again shortly after. We all fucked again a few hours later and then a few more times before Ariela got back from clinicals the following morning.
James was pissed. Johanna broke up with him the next week.
