Session 55

Sometimes I think it is not worth it. The pressure of running a world wide travel agency gets me down. Long ago when it was just me, it was way easier. I took care of my customers with absolute, superb service. I loved drowning them with personal attention, answering their calls for help 24/7 across the US then Europe.

Flight cancelled - I am on it. Hotel sucks, no problem. Car rental reeking of smokers, I got it. It seemed so easy back then, hard work, but extremely satisfying. Single and driven for success I was working `18-20 hours a day covering the time zones. It was not going to last. I needed steady revenue

I expanded to corporate customers, signing deals that exploded my revenue and profitability. I expanded my staff, carefully hiring the right stuff committed to my high level of service.

I solicited investors that bought into my vision. Go beyond booking, expand to vacation destinations. Why should someone else get the revenue for my customers and I only get a fee?

Funding my vision, we bought a cruise ship and a vacation resort. Both first class assets. We started a subtle campaign with both retail and corporate customers to use the companies assets for cruises and destinations, sometimes combining both in a package.

It worked.

The investors pressured me to buy more. I did, but I only committed to traunch 1, then 2 then 3 to control the expansion. I did not want to get out in front of my skis.

It was working, then I met Chris.

He was a talent on the cruise ship. He had something I liked. That night, I was not protected. Nine month later Melanie came into the world. He disappeared giving up his parental rights in writing.

The Board, which was mostly the investors, were rattled. My one outside member Sam was not. Sam was on my side.

The investors planned to push me out because they did not believe that I could be effective as Chairman and CEO with Melanie as a distraction. Sam and I agreed on a plan for the showdown Board meeting.

I called the meeting to order. My General Counsel Lane who was also Board Secretary would take the meeting notes.

'Gentlemen, you have concerns about my ability to manage this company because of Melanie and have requested a no confidence vote.'

My personal secretary on queue, rolled Melanie in via her stroller.

'I disagree with that. I believe the Board members should go on record with their views on this topic.'

'But, before we take a vote, I have an offer to all Board members. I will buy out their shares in the company to relieve them of their concerns.'

'Our GC has drafted, per my directions, my proposals to buy you out. Just raise your hand if you wish to receive your offer.'

'Lane off the record please.' she nodded.

'If you have a limp dick and do not have the balls to take a stance in front of your co-horts, please text Lane privately to arrange a meeting to review and approve my generous offer in 24 hours.'

'Lane back on the record.'

'No members wish to acknowledge the offer. Gentlemen, please decide in 24 hours if you choose to accept my offer.'

'Any questions or comments? Who wishes to call for the no confidence vote? None? No one? I have a comment.'

'Most of you used your wife's successful companies to make your investment. And most of you have children with your successful wife. It appears to me that a working mother can be quite successful.'

I waited 30 seconds.

'No other comments or questions? No vote to call? Meeting adjourned. Melanie, let's go home.'

***

Lane called the next day, no one wanted out, They dropped the no confidence vote. Not surprised.

That was 25 years ago. I grew the company into a publicly traded mammoth travel giant with a $750 billion dollar market cap. Along the way, I married and had Scarlett - a seven year gap from Melanie. The marriage lasted eleven years. When Melanie turned 18, Scarlett's Dad had sex with Melanie, seducing her into thinking she needed sex skills to find a partner. I caught him face fucking Melanie. I threw him out. The divorce was finalized in weeks. I gave him some money. After all, he was the father of Scarlett.

Melanie told me that it wasn't the first time he made her have oral sex. She said she hated it. He made her gag all the time, but he didn't care. He told her he was going to tell me that she begged him to do it. What a liar. She didn't know what to do so she put up with it. She told me she was turned off by men.

I love oral sex and always took care of Scarlett's Dad. Huge cock which I loved. I never understood why he forced Melanie to have sex. My only theory was he needed to dominate which he could not do with me. And... she lost her virginity to him. He was lucky she didn't get pregnant.

At Harvard grad school, Melanie met Ashley. He changed her mind about men. They fell in love and married after graduation. Harvard MBAs are a big deal. I was pumped up about the possibilities of Ashley and Melanie taking over the company at some point, both were busy savvy and ambitious. I would train them up right. I hit 50 so I have to think about a succession plan. I wanted to retire at 55 and enjoy life and travel for fun, not business. I was starting my fun early.

I still had my looks, worked hard to have a trim body and had an occasional lift here and there. And... my sex drive was still there, but you never know when it may die out. My dates were usually way younger than me, I liked the energy they brought. I am sure they enjoyed my oral skills. I just love the feel of an erect cock in my mouth.

Melanie would pester me about dating someone my age. She reminded me that most of my dates were Ashley's age. I kidded her that I would rather have two 25's than a 50.

We had an 18th birthday party for Scarlett in the Bahamas at one of my companies resort properties. We used the corporate jet to fly in style. One of my 25's was the pilot although he was closer to 30. We have plans for later.

We had a sumptuous lunch on the beach with a wait person for each one of us. What the heck, I was spending the kids inheritance on them. I had my eyes on Scarlett's waitperson. He clearly took care of his body. No hiding the muscles in the white Bahama shirt and matching shorts. His tanned skin blending nicely with his sun bleached blonde hair. His blue eyes were captivating.

He flirted with Scarlett, She was loving it. I was always amazed at the different body types Melanie and Scarlett had. Melanie, long black hair, dark brown eyes, high cheek bones, ample bosom with pilates sculpted ass cheeks. She stood about 5 foot 10, slightly taller than Ashley.

Scarlett looked more like a 14 year old right now. Relatively flat chested, blonde hair in short little pigtails. She had a nice bottom and legs, stood about 5 foot 5. She was in the last stages of braces, she started late. I saw her changing into her swim suit yesterday, she had a hint of pubic hair. A virgin. I wasn't overly concerned with his attention, but maybe I should be.

He knew who I was and maybe tried to make points with my daughter hoping that had a positive effect on me. The only positive effect on me would be if he and I... stop it.

I have my private pilot lined up for later. We were going to meet on the jet. He asked that I ride him while he was in pilot seat. A fantasy he had. I am so bad, I agreed. He called me his favorite MILF although he admitted he didn't have another.

All of us ladies were going shopping. Ashley of course said no. I had to tear Scarlett away from her now favorite wait person. We would be here for another week I told her. We were off! Look out Bahamas! Shoppers on the loose!

***

I waited about 20 minutes. I pulled out my iPad Pro, connected to the room WiFi. I used private mode to find my favorite site. Small Tit Teens. I loved those videos, I liked the puffy nipple videos especially. I hoped that is what Scarlett had. I fantasized it was her sucking my cock, bare chested with her little tits and puffy nipples well in my grasp. I pictured a hairless smooth pussy that I finger fucked till she was wet enough to take my cock. I hoped to see the real thing this trip, but more of a dream.

Yesterday, I started to sneak into the cabana where Scarlett was changing. iPhone ready for pics or a video. But her Mom was there, I retreated.

But all that was a means to the end. Melanie had no interest in oral sex, something in her past turned her off. She was straight laced in bed, missionary only, cum only in her pussy. Sometimes I thought she didn't like me, or just men. After about a year of asking for a blowjob, I gave up. I thought about contacting my old girlfriend who was the exact opposite. She spent more time sucking my cock, then I spent fucking her pussy.

But I loved Melanie and would not do that. After a while, masturbation was fine. I watched blowjob videos. When I met Scarlett, I switched to small tit teens. Still not satisfied. Then... oh boy... then... I ran across a self suck video site. That was for me!

I watched intently on how they did it, then researched how I could give myself a blowjob. I had a pretty good cock size, more thick, then length, but nothing like some of the guys and shemales who made it look effortless. Spread legs wide, dip down, take cock in mouth. stroke and overfill mouth with cum. I was so jealous.

The other method - laying on your back, legs raised and pulled up and over the self-sucker's head. Usually a side video view of the cock dropping down to a waiting mouth. Some able to take at least the head, some down the shaft, some close to deep throat, some just stroking cum out into the mouth and face. I decided to train for that position. It was a start.

I took yoga, swimming and pilates classes to fill out my physique and improve flexibility. I was extremely disciplined about it working on it for over a year.

Typical self-suck session, I would set my iPad up on one side of my body tuned to small tit teen videos, my iPhone on the other side recording my session. I used the recorded videos to refine my technique.

When I first started, my cock head was 3 inches from my lips. It was disappointing, but over the year I continued to get closer. Last session I was able to lick the underside of my cock head, enough to trigger a cum explosion. Watching the video became another satisfying masturbation option.

My next goal - wrap my lips around the cock head, all of the head in my mouth, lips below the corona. I would stroke and cum in my mouth. I had to do it. I was so excited. It was a goal worth achieving.

I figured I had hours for a self-suck session today. They were shopping. I moved to our bedroom, stripped naked and set up the iPad and iPhone. I watched my favorite Small Tit Teen video, one that always got me off. The girl could have been Scarlett's twin, short blonde hair in pigtails, puffy nipples, smooth pussy. Scarlett is going to give me a blowjob!

It didn't take much for me to get hard. I was worried that I had missed my exercise routine for three days. But... this might be my only chance to do this in the next few weeks. Moving into position, I spent a moment to admire the big head of my cock only an inch away. I stroked it hard and pulled it closer to my lips. I raised my head up, stuck out my tongue and made contact with the head. Yes!

Stroking harder, I felt like I gained some ground. I strained hard to move in close. My lips contacted the head, I pulled down hard and raised my head up further. My lips were under the head touching the shaft! It was a struggle to hold there. I stroked hard. I was so excited, harder, lips still in place, harder. My balls tingled. Precum leaking. One more stroke, the first explosion. I couldn't hold position, my head fell down, the cum continued to spray in my open mouth, some landing on my cheeks, some hitting my eye and blurring my vision. I kept stroking, all of my cum pouring out, leaving nothing in my balls.

My legs were weak so I dropped them to the bed. The recording turned off. I laid there for a second. Unbelievable, not a blowjob but heading that way. I was proud of myself. Such a load! Well it has been almost a week. Melainie was having her period. And... I wasn't even thinking about Scarlett! Progress.

The excitement of a cock in my mouth was something I did not anticipate. Maybe I like it too much? Maybe I... no, I can't picture me sucking another cock. But it was pretty damn exciting.

I looked at the video. Awesome, one of my better videos. I clipped off the dead slices in the front and end and saved it to my iCloud folder, I didn't notice which one. I would find it later.

***

We were shopping. Yes, look at everything mostly not knowing what we were looking for. My girls found some knick knacks and some interesting items beyond the normal tourist drivel.

I decided to check my emails. I saw that Ashley had shared a something called Session 55.

I asked that he share any pics on the trip with me. I opened it, a video.

Oh my God! What was he doing? Jesus Christ! He was self-sucking. What is wrong with him? Why is he sharing this with me? Is he sending a message? Was he showing off his thick cock? So thick, such a big head. I turned the volume down.

I could see an iPad. It was playing a video. I caught glimpses of a flat chested teen sucking a cock, she looked a lot like Scarlett.

'Mom, what are you looking at?' Scarlett asked

I was so surprised I dropped my phone.

'Mom, I can get it.'

I pushed Scarlett aside knocking her down to pick up the phone.

'Mom, that hurt.' She rubbed her shoulder.

'I am so sorry Scarlett!' I gave no other explanation.

'Were you watching porn or something Mom?'

'No, no, nothing like that. So sorry. Big problem at work.'

'I am sorry, should I get Melanie to help? Should I call Ashley?'

'No, no I got it.'

I walked away. My phone screen was cracked. I closed the video. Time to think.

***

I was going through the motions of shopping. I couldn't stop thinking about the video. I need to watch it again to confirm what I saw. I was in shock the first watch. But, what I couldn't get out of my mind was the thickness of his shaft and the size of the head. It stimulated me to think about it. It has been too long since I had a cock in my mouth, looking forward to tonight with my pilot friend.

Maybe Ashely and I can help each other out? I am sure Melanie is not helping him out, she told me she was totally turned off by oral sex due to the step-dad incident. Still not convinced she is OK with men, OK with Ashley. Mom's intuition.

No! He is my son-in-law, not just some big cock 25 year old. Stop it. Don't watch the video again I told myself. I should delete it, but I couldn't bring myself to do it. Maybe later after I make my plan to address it with Ashley.

***

Back to the resort I decided I needed some time in the sun to think about the video. I don't know how I will handle talking or even looking at Ashley right now.

Knock on the door.

'Come in, it is open.'

In walked Ashley and Scarlett. He was wearing the smallest white Speedo I have ever seen. I could not help but look at his cock which was bulging out of the little bit of cloth keeping it in check. The big head was neatly outlined. I had to look away but then I looked back. A tingle of desire rolled through me. I want it.

Scarlett was wearing her modest two piece swimsuit. Her nipples were pressing up against the white top. The bottom piece tight against her pussy, the lips easily seen. Need to talk to her about that.

'Hey Mom, Scarlett and I are going to surf a little bit. Want to join us?'

'No thanks Ashley, I am just going to work on my tan.'

'Got it, see you at the cabana!'

He held Scarlett's hand and they walked out. 24 hours ago, I would have thought nothing of what looked like an innocent, cute gesture.

I put out the do not disturb sign and double locked my door. I locked the adjoining door to Scarlett's room. I retrieved my skimpy bikini and laid it out on the bed. Nothing but strings and three small pieces of cloth. I still looked good in it. I convinced myself I would wear that to maximize my tan - yeah right.

I looked at my phone, I picked it up and crawled onto the oh-so comfortable bed. Way too big for one person. I opened up the video and was about to hit start when a FaceTime call came through.

'Hey boss what are you doing?'

It was Steve, my 25+ pilot.

'Well I was about to masturbate while thinking of you.'

I flipped the camera and showed Steve my naked body, showing him my breasts with a up close of the nipples. Down to my pussy. I squeezed my lips together, then slipped two fingers deep inside.

'Stop it! I am so turned on.'

'Take it out, let me see how much.'

He complied, he wasn't totally erect but getting there. He zoomed in on the head. A view I would have right before plunging down on him.

'I can't wait for tonight. I am so horny for you.' I said.

We flipped our phones back to our faces.

'You will have to wait a little longer. Your cruise ship EVP's assistant just called. He needs to be in Cozumel tonight, an active shooter incident on the Princess Scarlett. He is in Miami, can't get there with commercial. The other corporate jet is in Thailand. All your resort exes there for the opening of the new property. I am his only hope.'

I should have received a notification. I double checked, it came in right after the video. Shit. I should have seen it. So bad, totally distracted by Ashley.

'Well I could just fire him and let his second in command handle.'

Long pause from Steve.

'You would do that?'

'Either that or fire your company.'

We just leased the jets and pilots. He was speechless.

'Steve, that was a joke. Lighten up. Go take care of the situation.'

'OK boss. I was worried there for a moment.'

'Bye!' I hung up.

I was so looking forward to getting laid tonight amongst other things.

I looked at my phone. I picked it up. Opened the video. The start triangle staring back at me, the screen crack running right through it. I turned up the volume. I pressed the start. This time I paid attention.

I could tell he was setting up the iPhone to record and the iPad for porn viewing. Phone was on and recording. He was naked, his sizable limp cock laying on his pelvis. So desirable. Stop thinking that way!

He appeared to navigate to the video. I could hear the audio.

'But Uncle Jim, I am still a virgin, won't it hurt the first time.'

'Oh no Ann. It might pinch a little but after that you will love it.

She could have been a double for Scarlett, Same type of body, small chested with puffy nipples, smooth pussy but probably shaved.

'First, you have to help me get an erection. Will you do that for your Uncle?'

'Sure, what do I do?'

'First take off all my clothes.'

'OK.'

'Now move between my legs and hold my penis. Start by licking and kissing it, then take it in your mouth and gently hold my scrotum where my testicles are.'

'Ok'

'Good girl, can you tell it is getting nice and hard.'

'Yes Uncle Jim. I can't believe I am making that happen. It is growing so fast. I love it.'

At this point Ashley moved into his self suck position It was amazing how he just lifted his legs up in the air and over his head without effort, great for Amazon fucking, one of my favorites.

Nice camera view of the thick hard shaft and head dangling down to his lips. I was getting aroused, picturing that cock heading my way.

He kept stroking and pulling it down while forcing his head up.

I could hear on the video, 'Ann, stroke it harder, keep it in your mouth, I am going to give you a big surprise.'

Ashley picked up the pace, he was getting closer and closer, he stuck his tongue out touching the top of the head. He pulled down harder, moved his head closer. Contact! Lips halfway up the head.