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."
"Sensible."
"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 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?"
