My Best Flight Day 01

The names have been changed to protect the not so innocent. This is pretty much based on a real experience with some facts 'enhanced' for the reader's pleasure.

Day 1 – Tuesday afternoon

I was flying from New York to Orlando on business several years ago. I navigated down the aircraft aisle to my row and found an older gentleman in the window seat. I already knew that I had the center seat due to booking the flight at the last minute (Thanks boss). After getting seated and situated I had my paperback out and seatbelt on. Passengers were still boarding the plane. Over the top of the seats I noticed a very large woman patiently waiting as passengers were storing bags and wrangling children into seats. By large, I mean large. I would estimate at least 6'2" and over 400 lbs. Now, I have always been a fan of larger ladies but this woman was the freaking superbowl of big girls. She had it all. Big, full breasts, an oversized bottom, thick thighs and a very sweet face that always seemed to be smiling.

As luck would have it, she had the aisle seat to my left next to me. She checks her ticket to confirm her seat assignment and shoves her bag into the overhead. She looks at me (I guess I was kind of staring at her, she was just so overwhelming) and shoots me a little smile. She works her body into the seat and has to kind of push her soft ass cheeks and thighs in between the two arm rests one side at a time. Even after she is in her seat there is a lot of spillage of flesh. She was smart enough to prearrange the seat belt so there wouldn't be the hunting around after she sat down. I sat quietly looking forward while she arranged herself so as not to cause her any embarrassment. In my peripheral vision I saw her extend the seatbelt to the full length and attempt to connect the two pieces. It wasn't even close.

She said to me "Excuse me, would you mind pressing the call button please?"

"Sure" I said and reached up and pressed the blue attendant call button.

"Thank you" she said.

"Your welcome."

I took my paperback from the pocket in front of the seat and started reading. The flight attendant came over after the aisles were clear and the passengers were all seated. "Yes?" the attendant looked at our row.

The woman said "May I have a seat belt extender please?"

The attendant said "Of course."

The attendant stepped away to get the extension. I kept my nose in the book so this lovely lady would not feel self conscious.

A couple minutes after takeoff I folded up my book. I leaned over to woman and in a low voice said "Ma'am?"

"Yes?"

I continued, "I have always been a big fan of larger ladies and I am sure you are uncomfortable being squeezed in there. I would be happy to lift the arm rest to make you more comfortable."

She seemed honestly surprised at my offer. "Really? You wouldn't mind?"

"No, not at all. I am sure that our hips would be touching but I will probably enjoy that."

She gave me a look I guess sizing me up. I guess I appeared harmless enough and she said "That is the sweetest thing I have heard in a long time. Thank you."

We shared smiles and I lifted the arm between us up as she leaned to the other side to make room. Once the arm was up a wave of thigh washed over into my direction and landed right on me. She shifted left to right to redistribute her mass. She looked at me and asked "Is that all right?

"Just fine" I replied.

"Really, you don't mind this?"

I could already feel the heat radiating through her dress into my leg and was enjoying it "I really don't mind at all".

She shifted in her seat again to make herself more comfortable. I could tell that she was glad to have the extra few inches.

I went back to my book half heartily but was enjoying the sensation of feeling all of this woman in such a close environment. Between the vibrations of the plane, the sway of her softness against me and the heat transferring from her thigh to mine was awesome. I was becoming aroused. Apparently it was the wrong choice to wear boxers that day but I like the comfort. I couldn't help the erection growing in my Dockers. Soon it expanded enough and made a noticeable shift in my pants. To avoid embarrassment I closed my paperback and placed it in my lap. I folded my hands at my waist and tried to think of bland thoughts in order to relax. I turned to look out the window to get my mind off my dick and thigh when I felt a hand reach under the book and two fingers gently nudge my hard cock. I looked down and saw the woman picking up my book from my lap but she had slipped some fingers under to touch my dick.

She grinned and she lifted my book "What are you reading?"

Words were unable to be formed at this time.

"Is it any good?" She turned the book over and read the synopsis on the back cover.

"Uh huh" Was all I could manage at the moment.

She carefully replaced the book back in my lap and again used her fingers to feel my hardness for a few seconds before withdrawing her hand. She leaned in closer to me and in a low voice said "I guess you really do like big girls. I noticed your dick growing."

My face was now glowing bright red from embarrassment. That brought out a hearty laugh. "That's OK sweetie, I'm glad I inspired that reaction."

I didn't know what to say so I said "I don't know what to say."

She said "That's fine, your actions are speaking volumes."

This broke the ice and I figured she wasn't going to bust me as a pervert. I looked over at the older gentleman in the seat next to me. He was leaned against the bulkhead apparently sleeping. I took my book and slipped it into the pocket in front of me.

The woman said "I guess you want to have some fun. Am I right?"

"Yes I would. But you need to stay PG-13."

"Agreed."

I decided to get a little forward and see where this would go. "I'd like you to lean over and get my book. If it's OK with you I'm going to feel your breast when you do. I figure fair is fair."

If it was at all possible her smile got bigger. She took my hand and put it palm up on my leg just at the point of impact where the tit would hit the hand. She loosened her seatbelt a bit to give her some bending room. She then leaned over to get the book out of the pocket. Her massive boob hit my hand and I gave it a squeeze. She seemed to take a very long time to retrieve the book but eventually she sat upright. There was a twinkle in her eye, she was enjoying this too.

She leaned in close again and said softly "That was very nice. What can we do now?"

I replied softly, "I don't know. I really didn't have a plan for this."

"I know, me either. But it's fun, right?"

"Yeah!"

She took my hand and placed it in the area between our thighs. "Feel free, but be discrete please."

A quick nod and a slowly felt her thighs. I moved my hand up and down. Squeezing, rubbing, stroking. She was obviously enjoying it. She leaned in and whispered "I am going to lean forward. Please play with my butt."

I was hoping I could do that. I repositioned my hand to get it in place, ready to make a move when the opportunity presented itself. She game me a wink and leaned forward like she was looking out the cabin window and I slipped my hand behind and grabbed a handful of ass cheek. It was so big and soft, just like I like it.

When she leans forward she effectively blocks anyone from across the aisle from seeing in the row due to her size. She took the opportunity to rub my still hard cock through my pants while 'innocently' looking out the window. After a minute she gave me a quick squeeze to warn me that she is sitting up.

"This is so much fun. I really don't want to excite you too much and get precum soaking through your pants."

"I'm really loving this too. This is hot as hell." I said.

"I would invite you to the lavatory and get you off but I can barely fit in there alone."

"That's OK, I appreciate the thought. Is there anyway I could get you off here?"

She sat upright and looked at me. "Really, you would do that even though I can't do the same for you?"

"Sure." I said. "I'd be happy to."

"You really are the sweetest man I have ever met. That's so unselfish of you. Most guys I know work hard till they cum and then its snooze city. Don't know too many guys that are interested in my satisfaction without theirs."

I replied "Well, we are few and far between but are worth the search. So, what can I do for you?"

She pondered this for a moment. She leaned back in and said "I can get off from breast play but it's going to take a little bit of work."

"Do tell."

"Can you do the one handed bra opening thing? Keep in mind this has four hooks and is fairly tight."

I grinned "I am right handed and would have to use my left but I think I can manage."

"Here is what we'll do. Take it in nice, easy steps. First, I am going to twist around to look at the back of the plane. You unhook my bra. Then we'll take the next step. Try to be discrete please."

"Obviously" I said. I took a look at the older man seated next to me who was still leaning against the bulkhead with his eyes closed. I took my book and opened it holding it at just below eye level so I could watch the aisle for visitors. After seeing everything appeared normal I looked at the woman and nodded.

She turned to look towards the back of the plane. I slipped my hand behind her. After feeling around for the bra hooks I attempted to do the two finger unhook method. Her position further stretched the fabric and made it impossible to make any movement. For a woman of her size, her brazier is a major piece of equipment to be able to handle the weight of her massive tits. In only a few seconds she realized the issues involved and turned back forward. Then in a brilliant piece of improvisation she lifted her arms up as if stretching out her muscles after being confined to the seat for too long. She also rotated her shoulders backward. This allowed me to unsnap the hooks in two simple steps, the top two first and then the bottom two seconds later. She twisted left to allow me to slip my hand out then turned back to face me.

"Well done!" I said to her.

"Yeah, I forgot that turning like that puts a lot of stress on it."

"Nice moves though, it worked well. Now what?"

She smiled wickedly at me and then slipped a hand into the top of her dress as if scratching an itch. I noticed her right boob suddenly drop free of the cup.

"Now, I am going to lower my right bra strap over my shoulder and out from under my dress. I need you to pull it down low enough so I can pull my elbow out. That way it will hang only on my left shoulder and my girls will be free."

"But what about getting it back on?" I asked.

She laughed heartily, so loudly that several near by passengers turned to look in her direction. "That's not going to happen in this aircraft. I don't think I would have enough room in the bathroom. When we get to Orlando I will go into the ladies and readjust. You ready?"

I nodded in the affirmative. We both checked to confirmed that the other passengers had turned back to their own business and that the man next to me was still snoozing. I crossed my arms over my chest to put my hand in the right position taking the opportunity to diddle her exposed arm a bit. She grinned and pretended to scratch her shoulder again as she pushed the strap off her shoulder. I slipped a finger into her sleeve and captured the strap. I slowly pulled it down to her elbow. She slid her elbow back and then fake scratched again to release the massive breast. She gave a sigh of relief as she was free of the confining garment. I could see under the dress her tit had sagged and flatten out. I extended the fingers of my right hand to test the weight and was pleasantly surprised at the shear volume of tit meat presented to me. Our eyes met. She looked at my book and then looked at the pocket in front of me. I knew whet she was thinking. I dog eared the page and put the book in the pocket. I unfolded my arms and placed my hand in position to receive the breast again.

The next set of moves was a beautiful display of mutual pleasure. She leaned toward me and fumbled for the book with her left hand placing the right boob firmly into my hand and with her right hand she carefully went back to massaging my still hard cock. She moaned with pleasure but I can't say from which action. Since my hand was pinned under a huge breast I had limited accessibility and was frustrated in locating the nipple. She removed the book and placed it in my lap. Then she reached up and lowered the tray. Took my book and placed it on the tray and slid the tray towards me mostly hiding her right hand. Why hadn't I thought of this!

She moved back upright removing her hand from my crotch. I had a supreme look of satisfaction on my face. I leaned in and spoke softly. "That was so cool, I wasn't expecting that. Well played!"

"It all just sort of fell into place. I was planning on one thing and everything else just worked out well. How's that hard cock holding up? Any leakage yet? I don't want to soil those pants."

"I am incredibly turned on but am in good shape. I couldn't find your nip. Where should I be looking?"

Her smile was now ear to ear. She tried her best to half turn in her seat towards me which unfortunately broke most of our thigh contact. She was able to look more directly at me. She then slid her right arm under her right breast lifting it up and presenting it to me. She rested her head on the seat back looking at me. "That should give you good access now. Don't worry about being too rough. They can take it."

"Good to know." Readjusting my arms in the crossed position I felt around and located the very erect nipple. I began teasing it through the dress material and working over the entire area.

Her eyes showed me that she was enjoying the experience. She said "You know what is amazing to me? I don't even know your name. I have never done this before. It's really thrilling me to have all these people around and the possibility of getting caught."

I was enjoying tweaking the nipple and was amazed how responsive it was. I replied "I know, I was thinking about that a few minutes ago."

"What I'd really like to do is be able to jack you off under that tray."

"That would be amazing but I would cover the seat, floor and probably my pants. I guess a blow job is out of the question."

"In here? Yes."

I continued to discretely diddle her nipple which seemed to be enjoying immensely. Another thought crossed my mind.

"What are you doing after we get to Orlando?"

Her eyes opened wide. "No! I can't. I have to... I just can't."

"OK, it was just a thought. No pressure." It seemed like I hit a nerve.

Her body language changed suddenly. She seemed to pull away from me. She folded her massive arms over her boobs to hide them from the world.

After a moment she leaned into me and said, "Look, I am sorry for teasing you like I did but we have to stop. Now it doesn't feel right. You reminded me about what is at home. I am sorry. I was having a lot of fun with you."

I did understand the situation; she wasn't going to run off with some guy. She didn't even know my name. I took out a business card and pen. I wrote Orlando Suites on the back of the card and handed it to her. "This is me. My cell number is on the front and where I am staying is on the back. My offer to get you off is still open. No pressure, honestly. Don't tell me anything about you, I respect your privacy. All I ask is that if you decide to toss away my card, don't do it in front of me."

She took the card. "OK, but please don't expect a call."

With that exchange we returned to being to anonymous passengers on a plane again.

When the plane landed she got out of her seat quickly and took her overhead bag and never looked back at me. I didn't want to appear like a stalker so I waited in my seat as passengers slowly moved down the aisle. After about 20 passengers passed my row I stood up and looked for an opening to exit the plane. As I was leaving I noticed that the older man in the seat next to me gave me a grin and a wink. I guess he wasn't asleep.

I walked through the terminal slowly towards baggage claim, got my checked bag and went outside to catch the bus to the car rental lot. The bus arrived and I climbed aboard and sat facing the terminal. Apparently the bus had to wait a few minutes at the terminal. I noticed the large woman step out from the terminal rolling a checked bag behind her. She dropped the bag as a shorter woman came running up to her and embraced her hard. They hugged and kissed passionately ignoring the stares of the other people around them. As the bus pulled away I realized her issues. I knew she wouldn't be calling me but I had a fond memory of a great flight to keep with me.

I checked into the hotel, dropped off my bags in the room, washed up and headed back to the lobby for a good meal. The nice thing about business travel is the expense accounts. I could blow my full per diem amount on one great meal since I hadn't touch my food allowance for the day yet. At the Italian restaurant in the lobby I ordered a full bottle of nice red wine which always mellows me out, two appetizers and a great piece of veal. Not being a desert person I put the meal on the company card. When the wine was gone and headed up to the room. I planned on a nice shower and to masturbate to relieve the pressure that I built up this afternoon before I could try to sleep.

After unpacking my bags and getting everything ready for tomorrow's meetings I found the hotel supplied bottle of lotion next to the shampoo and conditioner. I had a few tissues ready and striped naked. I was laying alone on one of the two queen sized beds and was stroking away when there was a knock on the door.

"What the fuck!"

Who the hell could this be? Maid service looking to turn down the bed? Just my luck. I had to get up and grab my boxers before she let herself in and catch me in the act. Then there was another knock. I almost tripped moving to the door and pulling up my shorts just to avoid the embarrassment of getting caught jacking off.

Upon reaching the door I opened it a few inches and was surprised to see the woman from the plane.

She had a very serious look on her face and said "Hello David."

"Uh, Hi."

Just then the shorter woman stepped into view. She looked like she was seething in anger. She pushed the door open and walked in saying "We need to talk."

The larger woman followed and closed the door behind her. I was standing in my underwear by the bathroom as the two women walked into my room. My right hand had lotion all over it, my hardon still was sticking up and the lotion was laying on the bed where I left it. They stood by the bed looking at what I have been doing. The smaller one said, "Wow, you really are some kind of pervert, aren't you?"

"What?"

"I heard all about you two on the plane. You think you can feel up my girlfriend and get away with it?"

"I... I... Well..."

"All you men make me sick. All you do is think with your dicks. I bet you never gave one thought that she might be in a relationship. Did you?"

"Well, I just offered her more room. I couldn't help it if I got excited."

"I guess so, we can see you're excited right now. Bet you were spanking your meat thinking about her tits, weren't you?"

"Well, I got real worked up on the plane. I needed to release the pressure."

"These tits right here, they got you worked up?" The little one went over and lifted the big ones tits in her hands taking the weight. The larger woman groaned with pleasure. During the exchange my dick was headed south, but it suddenly reversed direction.

"What?"

"Sara said that you like big women. Is that true?"

"Yes, always. I haven't touched a woman under 200 pounds since college."