Escort Neighbour Pt. 03


Welcome to Part 3 of Escort Neighbour. I have to admit to genuinely wanting to see just how far Bill and Jennifer will take their relationship. I’m not plotting this story, I’m just rolling with it. Hope you enjoy.

Warning: There is a LOT of anal sex in this. If you don’t like that, please don’t read!

Nancy dropped me off at the airport Thursday at noon. Flights to Saint Thomas left early in the morning from Dulles and I would have to overnight. Nancy drove up to the passenger drop-off area, released the trunk, and kissed me on the cheek. I got out, went to the back of the vehicle and pulled out my carry-on bag. I said goodbye to Nancy through the back hatch and pushed the button to close the hatch. As soon as it clicked shut, she drove off. I waved at her.

I turned to the automatic sliding doors leading into the airport and took a deep breath. This was exciting and nerve-wracking. I was about to fly to Saint Thomas in the US Virgin Islands for a sexual weekend with my next-door neighbour and her female client.

The last couple of days had been a blur. Jennifer had taken care of everything. I provided her with my passport details and she took care of everything else. She said to head to the airline check-in, use the business class line, and pick up my boarding pass. She would meet me in the lounge. She insisted I wear a sports jacket, a white dress shirt with no tie, and nice loafers. And to only bring a carry-on.

I entered the airport, dragging my wheeled carry-on behind me and found the airline queues. I entered the business class corral and was met by a stewardess. She smiled at me, asked if I was business class, and when I said yes, she escorted me to the check-in attendant.

I provided my passport and soon I had a boarding pass for Dulles in Washington, DC. The rest of my check-in to Saint Thomas would be in the morning. The check-in lady told me where the business class lounge was and wished me a pleasant journey.

Security was a snap and in minutes I was walking past gates toward the airline lounge. I followed the signs and entered an elevator that took me up. The elevator opened and I walked into a luxurious lounge. Thick comfortable chairs were spread out all over. I noticed a self-serve bar, a small buffet line with steaming food and soups, TV screens filled with sports and arrival and departure times. A large circular desk met me and I handed over my boarding pass to the woman behind the counter. She checked me in and said my wife was waiting for me in a private conference room.

I blinked at that, and then quickly realised it must be Jennifer. She was calling herself my wife now. I smiled and headed toward the conference room in the back. A small corridor separated it from the main lounge and it looked private. I knocked at the door and in a moment the door swung open revealing Jennifer, dressed exquisitely in the finest business clothes for women.

She grabbed my lapels and pulled me into the room, kicked the door shut and kissed me hard. I let go of my carry-on and embraced her. We kissed passionately, lips mauling each other, tongues licking tongues and probing deep in our mouths.

I felt Jennifer fumble at my belt and I started pulling her skirt up over her ass. I pushed her backwards until her ass hit the table. I had her skirt up and reached between her legs and found her panty-less and soaking wet. She pulled my hard cock out and in one motion I buried it to the hilt in her pussy.

She moaned into my mouth. I lifted her slightly by the ass and deposited her on the edge of the table. She lifted her legs and wrapped them around my lower back and pulled me in toward her. We fucked on the table with passion. My cock loved her warmth and wetness; now a familiar welcome home. We fucked with practice and passion. It never got old. It always felt new and fresh.

We kissed the entire time, grunting and moaning into our mouths. Her hands pulled my head to hers. Mine cupped her ass and helped me drive deep into her pussy. We fucked for a good long time. Every second was memorable and delicious.

“I’m gonna cum,” she said.

“Good, me too.”

“In my mouth. I don’t want to be dripping cum onto the business class seats on the plane.”


“Uh-huh, mostly I need to taste you again.”

“Come then, hurry.”

And she did, a pleasant orgasm that curled her toes and had her holding me tight until it passed. It took everything I had not to cum with her. Her pussy clenched me hard and added feeling to my cock that almost took me over the edge. When her breathing resumed, her eyes opened.

“Thank you, Bill.”

Instead of responding I yanked my cock free, stepped back and gripped my cock hard. Jennifer pushed off the table and fell to her knees in front of me and sucked my cock into her mouth. I let go of my cock and ejaculated into her mouth.

Jennifer swallowed and made happy noises. I came down from my bliss and watched her suck and lick my cock clean. She hadn’t spilled a drop. Finished she stood gaziantep escortları and kissed me and smiled against my grimace. She knew I hated tasting my own cum and thrilled herself forcing it on me every chance she had.

She leaned back her head and smiled at me. “Hi, handsome.”

“Hi beautiful.”

“You look really sharp, Bill. You’ll turn heads looking like that.”

I snorted in disbelief.

She smacked my shoulder where her hands were placed. “Trust me, dummy. A woman knows. You’re very handsome, Bill. You have a confidence about you, too. It attracts women. I’ll point it out to you.”

I looked at her. Her makeup was flawless. Her hair perfect and shining red. I loved the freckles on her face and on impulse I kissed her. I watched her eyes widen a little. When I finished she looked questioningly at me.

“What was that? Not that I mind.”

“You’re so beautiful, Jennifer. I’m so lucky to have you in my life.”

Her eyes softened. “You too, Bill. I’m glad we met.”

“Best friends?”

She kissed me. “Always.”

We kissed for a little while until it started to get heated again. It was Jennifer that said we needed to stop and laughed when I pointed out my cock didn’t agree. She said she needed to clean herself up and dry herself off. I finally agreed and pulled up my pants and tidied myself up.

Jennifer pulled down her skirt and then stepped up to me and placed a hand on my chest and kissed me on the lips. “So handsome.”

She smacked my ass and told me to head to the lounge and get her a drink. She asked for an Irish whiskey on the rocks with water, turned me toward the door, and then pushed me out of the room. I only just managed to grab my carry-on.

I wheeled it past the woman at the entrance counter. She was really cute and dressed in the airline uniform with a scarf around the neck. She looked at me, her eyes opened wide, and then beckoned me over to the side entrance. When I stepped into the opening, she stood up and came over to me looking around to make sure she wasn’t noticed. She pulled out a Kleenex and wiped my mouth with it.

“A little lipstick, sir.”

I blushed hard and she chuckled. She took a small sniff and then arched her eyebrows at me.

“How was your conference with your wife, sir?”

“Uh, uh, fine?”

“Mm-hmm,” she murmured. “There, all done. Have a lovely day, sir.”

“Uh, thanks?”

She smiled at me and returned to her station. I wheeled my carry-on into the main lounge and found a quiet place by the window that looked out onto the runways. I dropped off my bag and then went to the bar and fixed two whiskeys and returned to my seat. As soon as I sat down, Jennifer walked into the room.

She stole my breath away. Her poise, the way she walked, the way she held her head drew looks. She was a powerful woman. She exuded confidence. Man looked at her with lust, and women looked at her with envy. I could see the airline lady at the front counter tracking her and then saw her look toward me. An expression crossed her face that I couldn’t fathom.

I rose when Jennifer came close and handed her a whiskey. We clinked glasses, sipped our drinks and I waited until she seated herself before sitting down.

I smiled at her. “You looked stunning crossing the room. You owned the place.”

Jennifer laughed lightly. “Years of practice. I actually took classes on how to do that.”

“Looks natural to me. You are a thing of beauty, my dear.”

“Thank you, darling. I have to admit hanging off your arm is going to boost my worth. You look all sorts of dashing. You really dress up well. Betty is gonna love you.”

Betty was her client in Saint Thomas. She had paid for our travel to Saint Thomas. All expenses were covered. This was the life Jennifer was used to, but not me. I felt like I was playing a role. “Tell me about her, this Betty.”

Jennifer pulled out her phone and spent a minute scrolling through it. I had never wanted a smart phone. I had no use for one and it annoyed Jennifer. She said she wanted to text me all the time. She handed her phone over to me. The screen was filled with a picture of a couple sitting close to one another at a restaurant table smiling at the camera. The man looked about my age, but with more hair and a little more grey. He was deeply tanned and his teeth looked perfect.

The woman next to him was stunning. She looked like a porn star I had seen, but one who had aged really well. Plastic surgery had to be the answer to her gorgeous face. Only the slightest wrinkle around her eyes gave her away. She was blond and I could see the tops of what appeared to be massive breasts at the bottom of the picture. She wore fake eyelashes, bright red lipstick, and her smile was wide and gorgeous. She was a real looker. “Wow,” I said and started to hand the phone back to her.

Jennifer shook her head and told me to swipe the image.

I did and the picture changed. I could now see everything nature had given Betty. She was lounged back completely naked on a couch, sitting back with her legs spread. Her breasts were massive but clearly man-made. They were gorgeous though. Her areolas were massive with thick, protruding nipples in the middle like little towers. Her pussy was completely shaven. Not a hair or blemish could be seen. Her clit was the largest I had ever seen. Her inner labia was small and I could see right into her gaping vagina. I noticed a C-section scar on her abdomen. She was gorgeous, clearly an older woman, but well-preserved.

I swiped again and was treated with an image of Jennifer being eaten by Betty. It was fucking hot. I could see the pleasure in Jennifer’s face and knew it was real. I swiped again and again. The images changed position of the two of them. I guessed Betty’s husband was taking the pictures. I froze when the next picture was Jennifer with a strap-on sodomizing Betty. I swiped again and this time it was a real cock sodomising Betty. I could see the strap-on buried in her pussy.

With my hand shaking I handed the phone back to Jennifer. I grabbed my drink and took a big gulp.

“What do you think?” she laughed.

“Unreal. Fucking hot.”

She glanced at her phone. “You stopped when Betty’s husband entered the pictures.”

“I stopped when my heart couldn’t take anymore.”

She smirked at me. “This is gonna be so much fun, Bill. I’ve never travelled with anyone before. Not like this. With a client sometimes. But that was all business. This is fun.”

I calmed down and squirmed a little when my cock, hard again, strained against my pants. Jennifer watched my crotch and sipped her drink. “So far, this has been the best. Betty is really good looking. How’d you meet?”

Jennifer looked out the window and watched a plane roar down the runway and lift off. “They found me.”

“Through your website?”

She looked over at me and smiled. “No, they found me in the Ritz-Carlton in New York, half-dressed, drugged, and clearly out of my mind.”


* * *

Jennifer was messed up. She knew it. She had gotten away, though. From what? She couldn’t remember. She sat at the bottom of the elevator car in the corner. She was missing her shoes. Her stocking feet were covered in what looked like caviar. Her skirt was missing, too. Oh no, wait, there it is, torn off and lying beside me.

The elevator dinged and she pushed herself off the wall to stand up. Her balance was messed up. What happened? Where am I?

The doors opened and noise filled the elevator. The sound of conversation flooded her ears and she held her hands up to her ears to block it. She staggered out of the elevator and right into a couple waiting to get in. They caught her as she slumped forward. She felt herself being sick and then all went black.

She woke in a bed. It was dark. Her head pounded horribly and she moaned. She heard a rustling near her and the face of a woman swam in front of her eyes.

“Shh, it’s okay, you’re safe,” said the woman.

“Safe?” asked Jennifer. She tried to remember where she was. New York, she remembered. The Ritz.

“Yes, my dear. You were drugged with a date rape drug. I don’t recall the name.”

“Date rape drug?”

“Yes, it seems you recognised the symptoms just in time and escaped.”


“Yes, your companion. Room 1516. Security has handed him over to the police. Your belongings are here with my husband and I. You’re in our room. My husband is with the police giving a statement. The hotel doctor drew blood. I hope you don’t mind. We needed evidence.”

In a flash, Jennifer remembered everything of the day before. She had met her client here in New York. Went to his room. They were to spend the weekend together in New York. He was new but recommended by a client she trusted. She went into his room. Met him. He gave her a drink, they ate caviar. Then she remembered feeling strange. She tried to leave. He fought her. She… Oh my god, I stabbed him!

“Oh no!” said Jennifer and tried to sit up.

“Shh. It’s okay. Your companion was seen by the doctor. It was a superficial wound. Minor. He’s pressing charges against you. But don’t worry about that. It’s a clear case of attempted rape. He’s fucked, if you don’t mind my expression. Lovely, really. We even have footage of him coming out the hotel room after you. He says all sorts of interesting things.”

Jennifer sank back and tried to relax. “How?”

“I’m Betty, by the way. My husband is Roger. The fellow you were with is an adversary of ours. Business adversary. He’s going to jail, my lawyers – your lawyers now – will make sure of that. Suddenly my business ventures are looking up.”

“I don’t understand.”

“This incident, and having that bastard thrown in jail, will probably net me close to two hundred million dollars, young lady. So you relax right there. The doctor told me to give you something when you woke. I’ll go fix it up. You’re my guest and I’ll take good care of you, my dear. Lie back, sleep if you can. Okay?”

Jennifer sank into the pillow and sighed.

“I know who you are, Rachel.”

Jennifer said nothing.

“Roger and I looked at your website. Then we made a few calls. We know quite a few of your clients. I’m only saying this because I want you to know you’re safe here. We respect what you do. We have your belongings here. We had to go through them to see who you were. So, Jennifer is your real name? From Canada?”

Jennifer hesitated then nodded.

“It’s a pleasure to meet you, Jennifer. I used to be a stripper before I met Roger. Get some rest. I’ll get your medicine.”

Jennifer looked at me and waited for me to say something. I watched another plane take off outside the window. I didn’t know just how dangerous her life could be.

“You seem to have all sorts of trouble,” I finally said into the silence.

“It’s how I met Betty. She did porn and stripped all over the US before she met Roger. They fell in love, got married, and had a kid. They’re swingers. They crave sex all the time.”

“What happened next?”

“They took care of me. Got me back on my feet. I gave testimony to the lawyers. I never saw the police or talked to anyone other than Betty and Roger’s lawyers. Next thing I knew, it was all over. It was settled out of court. I signed some paperwork, was handed a check for five hundred thousand dollars, signed a non-disclosure agreement and went home. It took four days to settle.

“The check was the first of four. I was given two point five million dollars to keep my mouth shut and drop the charges. Betty and Roger were able to progress some deal they were after and after my client was forced to back off, they landed it and secured some prime real-estate in Manhattan.”

“Who was your client?”

“I’m not allowed to say. Everyone knows him. He has a history of abusing women and paying them off.”

I blinked at her. “Are you serious? Him?”

She nodded.

“The good that came out of it was I met Betty and Roger. They started hiring me and they insisted they pay for my services. I meet with them about twice a year. Usually somewhere warm and sandy. They know me better than anyone else. I love them and they love me. They take care of me. Watch out for me. I send them new client information now. The details I mean. They run checks and tell me yay or nay. They say they’re my pimps!” Jennifer chuckled. “They’re so good to me.”

“And what do they get in return?”

Jennifer raised an eyebrow at me. “Are you kidding me? I fuck their asses off, Bill. Happily, I might add. Sex with them is amazing. I swear I lived for it until I met you. You’re a lot like them, Bill. Kind, caring, gentle, and so sure of themselves. I’m attracted to that. Strong, good people.”

“Okay. I’m glad to hear you have good friends like that.”

“They are good friends, and I love them, Bill. But I only have one best friend. And that’s you.”

I stared at her. I didn’t understand why she had chosen me. “Why me?”

Jennifer looked away and didn’t answer.

I sighed and rose and got us another round of whiskey. I doubled the amount. Jennifer took hers without a word and sipped.

We sat quietly for a few minutes before Jennifer stirred.

“You’re my best friend because you are. Bill. Don’t ask me why. I have never talked about my life with anyone. Not even Betty and Roger. Not like with you. I trust you and I don’t know why. I just do. So don’t ask why, okay?”

I nodded. “You are mine, you know. I haven’t had a best friend since high school. Then I was married and imagined my wife was my best friend. You hear that all the time: my wife is my best friend, blah blah blah. I don’t believe that. My wife is my wife. But you? You’re my best friend, Jennifer. My only friend. I’m sorry I asked why. I shouldn’t have. I’m just not used to this. I’m gonna say lots of stupid things.”

Jennifer nodded and I could see her eyes were a little wet. “You are pretty stupid.”

I laughed and in a moment she joined me. She smiled at me and then wiped her eyes careful not to smear her makeup. She raised her glass and toasted us. “To us, best friends forever.”

“With benefits,” I added.

“Oh yes, so many benefits!”

* * *

The journey to Saint Thomas was amazing. We boarded our plane to Dulles and I enjoyed first class for the first time. Jennifer and I were treated like royalty. At Dulles we took a limo to a nearby airport hotel and retired to our room. It was a simple room, with a king-sized bed, but had a Jacuzzi whirlpool bathtub.

We made it our home for the night. We drank and fucked in that tub until our skin was so wrinkled we escaped just to dry ourselves out. We climbed in bed and then realised we were going to sleep together — actually sleep. Jennifer couldn’t wait and snuggled up naked against me and draped a leg and arm over me and laid her head on my chest.

I smiled when she fell asleep in seconds. It took me longer. I was enjoying the feel of her in my arms.

I woke to a blowjob. Then we fucked, showered, made out again, dressed, and headed to the airport with a croissant and coffee in hand.

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