Me, The Stranger and the Redeye to Boston

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Chapter One:

On September 4th, one of my college friends was scheduled to get married in Boston. Usually, when I have any kind of trip planned, I’d take the day before and the day after off, just to account for Murphy’s Law. For some strange reason, I decided to work on that Friday, get off work at 5:00 pm to make it to the airport in time for a 7:30 flight.

One would think I’d have ample time to get to the airport, however, as I drove along in my car on the interstate and witnessed the sea of cars in front of me, nearly at a standstill, I thought, fuck…I just might miss my flight.

As I’m sitting there in the clusterfuck of traffic, one of my jams by H.E.R. sounds through speakers, “baby the sound of you, better than a harmony. I want you off my mind and on me…”

Shit, instantly I was feeling like sexing. Especially since I had not had any human dick in almost three years. My last experience left me traumatized and disappointed.

He was a handsome man, African American. Had this amazing smooth dark skin, tall, so I knew he was going to have a nice-sized cock. We had gone on a few dates and had several phone calls, so I figured it was time.

Now, one of my favorite positions is the cowgirl. I love to sit on that long stick and glide my pussy to the tip and twerk on the shaft while looking right in a man’s eyes, holding his chin and saying, “You like this pussy, don’t you.”

So, I was so ready to fuck this guy’s brains out. I had gotten my Brazilian. She was nice and clean and ready to enjoy. 

He came over and we sat on the sofa, on some Netflix and chill vibe shit. He’s acting all shy, so I decided to straddle him playfully and start kissing his neck and nibbling on his ear lobes. I felt his cock come to life and I was excited to finally be able to enjoy some dick…since I tended to have serious dry spells because I was such a workaholic.

He unzipped his pants and I saw that long wonderful masterpiece. I stroked it in my hand and bit my lip. I stood up and removed my clothes, then kneeled to give him head for a minute, while playing with his balls.

It was a challenge trying to fit all of him in my mouth, but I was always up for a challenge, so masterfully I willed that huge cock in my mouth and hummed on his dick.

Finally, I was ready to mount him. Now my pussy stays nice and tight. I do Kegels all day while sitting at my desk and use my yoni eggs to practice muscle control; so, when I ride I can hug the shaft tightly. All I needed was a good five minutes on his dick and I would have been good for at least another six months.

As soon as I inserted his fatty into my tight wet hole, he grunted, “oh fuck.”

I was thinking to myself, he better not. I stroked once, then twice and by the third stroke, he gabbed my ass and said, “Ahhhhhhh, shit.” 

I eyed him with contempt. I was frustrated. All that build up for the moment and not to mention all that shit he talked on the phone about going all night and he barely lasted thirty seconds. Then had the audacity to say, “Did you cum?”

Sir, if you have to ask, the answer is, “Fuck no.” But there was no way he was about to leave me hanging. He was going to eat my pussy until one of us got dizzy. I lay on my back and opened my legs. He commented, “I don’t do that.”

I laughed, “You should. And since I didn’t cum, you owe me a nut.” He felt guilty, so he finally got between my legs. He kept kissing my inner thighs. I reached for his face and said, “Tongue, lick it,” as I showed him my pearl.

He started hesitantly, but after the first few licks and he heard me hum, he started lapping up my juice as if it was a bowl of warm milk. I started humping his tongue and finally, I moaned, “Shiiiiiiitttt.” My heart raced and I was content for the moment.

He convinced me that his stroke game was indeed good, it had just been a while and my pussy was so tight, he couldn’t help himself. He asked to let him try again. I smiled as he massaged his cock in front of me getting himself ready. 

He inserted and started pumping, but his hip action was stiff, he grunted and made faces and I knew he wasn’t going to last long. It was such a shame; all that beautiful dick and he had no idea how to use it.

After that night, I politely told him it wasn’t going to work out. I needed a man that was skilled at fucking. Someone who could handle tight pussy like a champ and not buckle under the pressure of me coking their cock out with my walls.

I laughed out loud for the moment as that memory flashed in my head. I was wearing a wrap-around dress that tied in the front that went to my mid-thigh. I had one hand on the steering wheel and my right hand touched my clit. I figured, if I’m stuck here, I might as well enjoy myself and make the most of my time.

For some odd reason, I looked to my right and I saw this mixed-race Hispanic man sitting in his truck looking down into my vehicle enjoying the show. I could tell that he was stroking his cock because he had that “oh” face going on while biting his lip. 

I pulled my fingers out of my pussy and showed him my juices. He smiled and motioned for me to lower my window. So, I did.

“Hi beautiful, what’s your name?” he asked as he looked down at me.

“Lelani,” I replied.

“Can I take you out tonight?”

“I would love that, but I’m on my way to the airport. I won’t be back until Sunday evening.”

“What about when you get back?”


He asked for my contact information. I told him my Instagram name. Moments later, I got a notification that I had a new follower named Mario. I smiled and followed him back.

The traffic finally started to clear up and we had to say our goodbyes. I watched him get off at an exit before Tampa and I headed to the airport.

Chapter Two:

Just when I thought, I might get to the airport on time, I ran over something and a tire went flat. It was just a crazy day. I was beginning to think I was never going to make it to Boston to witness my friend get married.

When I arrived at the airport, it was almost eight o’clock. My flight was long gone. I was able to book a redeye that departed at 11:25 that night. The ticket agent could see that I was frustrated and had had quite a day. She said, “At least you’ll practically have the whole airplane to yourself.”

I smiled. I received her perspective, after all, that little traffic jam did allow me to relieve some sexual frustration and allowed me to meet Mario. I was excited at the possibility of riding his cock when I got back. I smiled as I began my walk to the gate waiting area.

As I approached the area, I saw this older White man, very distinguished. He had sort of a Pearce Brosnan vibe. He had salt and peppered hair, with a beard and mustache, he wore glasses and I could tell he was fit as he sat there checking out my ass, as I strutted by.

I sat in the seats across from him. He halfway looked at an iPad,  then stared at my legs. I was a gymnast in high school and college and my legs were extremely toned. I grinned inside as I sat sending naughty messages to Mario.

He had sent me a picture of his cock, nice and full, “Thinking about you.” It read. 

I smiled, “I can’t wait to get back. I want some of that cock in my mouth and my pussy.”

When I looked up, Mr. Distinguished stranger smiled as if he knew I was being naughty. I returned the smile.

The time to board had arrived and I grabbed my bag and went to check-in. I found my seat in business class and sat by the window. Moments later, I saw the handsome blue-eyed stranger walking down the aisle. 

He put his bag away and smiled, “Hope you don’t mind. I know the airplane is near empty, but I would love to sit here.”

I nodded, “It’s fine.” I replied as I watched him take his seat.

I sat, content with trying to take a nap, but I was getting serious vibes from the man sitting next to me. I decided to look over at him and I saw him scrolling through a playlist checking out songs by H.E.R. 

I smiled. He looked, “Do you know about this artist?” he asked. I thought to myself, of course I know…how do you?

“I do. And you like H.E.R?” 

“Yes. I also listen to Jazmin Sullivan and Eryka Badu, Jill Scout. My kids keep me up on the best tunes.” He saw the shocked look on my face, “What? Is it because I’m an old white guy?”

I laughed, “I’m just surprised and you’re not old.” I said flirtatiously. 

He blushed, “I’m fifty-two. And you must be like what twenty-three?”

I shook my head, “I’m thirty.”

He smiled as if he was now considering me a viable possibility.

After the airplane took off, we had a few cocktails and we sat telling stories about trips, music, and favorite foods. I placed my hand on his thigh and every time I laughed, I’d glide my hand up his leg until I felt his package. He looked around nervously.

I reached for a blanket that was provided and placed it over our laps. I opened my legs wide, draped my right one over his left leg. I found his zipper and went inside to find his cock full. The length of it felt nice and I peeked under the blanket to see it. It was pretty, all veiny, and had that nice mushroom tip. I stroked him nicely under the blanket while placing my lips on his neck kissing until I found his mouth.

He paused and removed his eyeglasses, reached over with his right hand and found my clit, started massaging it in a circular motion. Our eyes were locked, occasionally we’d look up to make sure the coast was clear. It felt naughty, dangerous, and extremely fucking hot.

His two fingers found my wet center and slipped in and out. I started humping his hand. It felt so nice to have someone other than myself touch me below. “Are you normally this friendly with strangers?” he asked.

I shook my head, “Actually, I haven’t had sex in three years and I’m dying to fuck someone. I figured why not a handsome man like yourself.”

He smiled and continued fingering me to my delight until I let out a soft sweet moan in his ear. 

“You’re so sexy and beautiful,” he said. This was true. I had what most people called an exotic look. My father was African American and my mother Polynesian. I had deep caramel skin, flawless, almond-shaped brown eyes, high cheekbones, jet-black wavy hair that reached my shoulder blades.

“Would you like to meet in the restroom?” he asked. I nodded. He adjusted himself and left. A few minutes later, I followed him. Mostly everyone had fallen asleep or was not paying attention to anything but their phones.

I stepped into the restroom, saw his dick standing at attention. I thought about all the fun I could have riding his huge cock, but with the space being so tight…I’d have to settle for being fucked on the sink, doggy style or fucked against the wall. I was down for either, maybe if time permitted, we could do all three.

I untied the strap that held my dress closed and opened up so he could see my amazing body. Tiny waist, toned legs, thick ass, tits nice and full. Immediately, he pulled me close, kissed my mouth, and then started sucking my nipples. This was a man with experience, I knew he was about to fuck me good and put me to bed.

He kneeled and pulled down my panties, then licked my clit repeatedly. My hands were in his hair. His hands gripped my ass, “fuck.” I said. He continued until I dripped on his chin. He stood and smiled.

I went down and filled my mouth with him, I licked the tip and tasted him. He held my head and fucked my mouth to his delight and when he had had enough, he said, “Turn around.”

His strong hands parted my ass cheeks and I felt him penetrate. “Ummmm.” I moaned as I took all of him inside of my tight wet pussy and started squeezing. I felt all those veins rub against my walls; I was ready to pop. 

He stood still for a moment and let me throw it back on him. He watched as my ass jiggled and my pussy swallowed his cock. He reached around pulled me up, so I could see our reflection in the mirror. His hands caressed my thighs, then my clit and then he held my breasts. I had not been fucked that well since senior year in college with my ex-boyfriend. 

His pelvis slapped against my ass, my tits bounced, I moaned, he whispered in my ear, “You’re about to cum for me, right baby. That’s it, cum all over my dick.” He bent me over so he could see his cock gliding in and out of my hole, “yes, that’s it, I see it, that’s nice.” he said as I creamed all over him.

He slapped my ass and picked up the tempo. I knew he was about to bust. He held my hips tightly while thrusting and finally, he pulled out. I turned and reached for his cock and stroked it in my hand until all of his cum oozed out. “That was fantastic,” he said. 

“It was,” I replied. We got cleaned up and went back to our seats like nothing ever happened. 

“I suppose I should let you get some rest before the plane lands.” He commented.

“Thanks,” I replied and then I fell asleep.


Chapter Three:

Wedding day. My girl Jade had a simple ceremony with family and friends and a hotel near the harbor. It was the first time; I met her man in person. 

“This is my husband, Bill Harris.” Said Jade. He was a handsome young man, our age, dark brown hair, tall, darling blue eyes.

He reached out his hand to shake mine, “Nice to meet you, Lelani.” he said. 

We were taking pictures when he said, “I want one with my dad too.” He looked around then walked off and returned moments later with his father, “This is my father Richard Harris,” he introduced him to the group.

My eyes nearly popped out of my head when I saw that he was the Stanger that I fucked on the airplane. He shook my hand, “Nice meeting you.”

I nodded, “Likewise.”

As the night progressed, everyone danced and had a good time, I was taking a break away from the noise, when he walked up, “small world.”


“Are you staying at this hotel tonight?”


He nodded. “Would you mind at all if I visited you tonight? I’d like to show you what I can do when I have more space and opportunity.”

I grinned, reached inside of my clutch, and handed him one of my card keys with the room number.

When the reception was over, and everyone had gone their way, I went to my room to prepare for my visit with Richard. I was excited to get a chance to twerk on his pole. I had intentions of making him say my name. 

I was wearing a tight halter top that barely covered my breasts and a thong when he entered the room and saw me standing by the window. He walked over and placed his hand on my ass and rubbed. I leaned in to kiss him, but he placed his hand in my hair, pulled and turned my head so he could kiss my neck and then he sucked my nipples through the shirt, later lifting the shirt to squeeze my breasts. 

“I’ve been thinking about licking your pussy since we left the airplane.”

I smiled. I took off my thong and walked over to the bed and opened my legs wide. I watched as he undressed and I strummed my clit, getting it nice and juicy so he could sip, lick and slurp and he walked over and did just that.

He locked my thighs in position and French kissed my lips, then flicked my clit with the tip of his tongue. I was shaking. I tried to squirm, but he held me in place until I nutted all over his lips. He gave it one final kiss before laying on the bed. His dick standing at attention ready for my mouth to savor all of that precum that was on his tip.

Up and down, I let my tongue wet his shaft, then polished his tip, sucking on it like a blow pop. He pushed it in and I hummed on it. When he was sufficiently satisfied with my performance, he said, “You want to ride my cock?”

I nodded. He waited and watched as straddled and mounted him, slowly we watched it disappear inside of me. I was in ecstasy. A nice long pole to twerk on and it was lasting more than twenty seconds. I had my fingers in his mouth while working my magic. I felt a wave come over me. I paused to enjoy my orgasm, but he pulled me into him, spread my ass cheeks, and thrust with reckless abandonment from below. I thought I was going to make him say my name and there I was, “Oh fuck, shit, Richard, baby.”

“That’s it, cum all over my dick.”

After I climaxed again, he said, “Turn around.”

I put my ass in the air. He pulled my legs out, so my belly rested on the bed, my ass spread, he licked up and down, then I felt him dive into my pool once and again, grinding and thrusting. His hands reached around and he played with my clit, while kissing my back, shoulders, and neck. I turned my head and he slipped his tongue in my mouth for a quick kiss.

And just when I thought he was done, he pulled out and said lay on your back. I turned and he placed my feet on his chest, while he dug me out quite nicely, then he let my legs down, hovered over me, pushing and pushing, going faster and deeper, until he said, “You want it inside?”

Since I was on the pill, I said, “Yes.” He released and then collapsed in my arms. We were both panting and moaning still glowing from the residuals of our orgasms. 

He rolled off of me, “What time do you leave?”

“Tomorrow at ten.”

“Should I let you rest?”

“Do you want to leave?”

“I want to stay and have you for breakfast and then take you to breakfast before you go.”

“I’d like that.”

In the morning, we enjoyed one another for a snack in sixty-nine. Then had a quickie in the shower before going to eat breakfast. It was 9:00 am and it was time for me to head out. He kissed my mouth, “Thanks for making this old guy feel young again.”

I smiled, “I had a great time.”

He started to leave, but paused, “I come to Florida like once or twice a month for business. Would it be okay if I called you sometime?”

My face lit up, “Of course.”

“Safe trip.” He left.

I headed to the airport and got on my flight. As I sat there by the window, I smiled. My Friday had started a hot mess, but then, meeting Richard was like a breath of fresh air. 

I smiled thinking about him visiting me in Florida. I received a message from Mario, “How was your trip?”

“It was fantastic,” I replied.

To be continued…