True story by Skybear

To set the stage, about a month ago at a impromptu party, things were getting crazy when this woman remarked that she was learning how to scuba dive and tomorrow was her first open water dive. She went on to say too bad she was on her period. I casually made the remark her husband was gonna get lucky tonight. In explaining my remark I stated when wifey was on her period she would get really horny and we would have great messy sex. The slightly tipsy lady made a statement along the lines of her bastard husband would not touch her during her period… he thought it was dirty. Tall husband just smirked and walked away. Of course me being a gentleman, I suggested she give me a call and I would be happy to help a damsel in distress. I also told her to call next month if she would like to go diving since I know all the good dive spots in the area. Lots of laughs and the party continued with her and I talking about diving.

Now almost a month later I get a phone call at the office from this same lady, let’s call her Linda. Linda is asking if I was serious about taking her diving, she has finished her dive course and wanted to learn about spear fishing. I asked the usual questions when, where, who’s going. Linda wanted to go the next week on Wednesday or Thursday and did not have anyone but her. Strange only those two days?

Well, I looked at my calendar and Thursday morning was open with a late flight to New Orleans that afternoon. We talked about her bringing her new wetsuit and dive gear, I would have everything else.

Thursday morning the boat was ready, tanks and dive gear on-board, she arrived early which was a nice sign. She nervously asked if anyone else was going, as I answered no just us, is that OK? She just smiled and said great, I’m excited.

Lines were cast off and the obligatory blast of the horn as the Sea Ray, Nauti***** slid from her slip. We were up on the fly-bridge with her sitting in the other seat when I asked if she wanted to drive? With a big grin she slid beside me saying she had never driven a big boat. Here ya go, throttles, wheel, GPS follow the dotted line. With a little encouragement she managed to keep the boat on track, 4200 RPM from the two engines we cruised out to the Gulf of Mexico. I noticed her beautiful leg stayed in contact with my leg as we talked about diving and how to use the spear gun.

Anchor was deployed over a dive site in 55 feet of water as we went down on deck. After demonstrating the proper use of a spear gun, Linda stripped to her bikini (very nice) and put on her light weight wet suit that only seemed to enhance her body. Big Boy was taking notice and beginning to stir so I quickly donned my wet suit top and helped her into the dive gear on the swim platform. (BTW, my mask still had a slight odor of female pee from Special Friend.)

Once in the water we swam to the bottom as she picked out a fish to shoot. Her first several shots missed and I could see she was frustrated so I signaled to go up to the boat. Arriving at the surface I suggested she relax and take her time since it was only for our lunch. A few additional hints and back down we went, this time I helped guide her to a lazy bunch of B-liners and maneuvered her in close as she pulled the trigger. I could hear her squeal as the shaft struck the fish in an almost perfect shot. We removed the fish and put it on my stringer as I looked at her air gauge we needed to head to the boat (new divers tend to forget to check for air).

Linda was so excited at her first fish all I could do was laugh as she gave me a big hug. With full tanks we went back to the same spot so she could shoot two more fish.

Back on the boat I cleaned and cooked the fresh fish as we sipped wine and enjoyed each others company. She was talking 90 miles an hour obviously tense as all get-out.

After lunch I asked why she has so much stress and suggested a massage explaining I had taken several courses in massage technique. Linda gave it some silent thought until I said there was one rule, “stop means STOP”

I went down to the cabin for my oils, towels, etc and on impulse I put on my Doctor Feelgood lab coat. Back on deck Linda looked at me laughing asking what is this? Oh, I am also an amateur gynecologist known as Dr. Feelgood. Now stretch out on your tummy.

I began with a slow massage of the neck and shoulders, feeling the tension as I pulled oiled hands down her back to her waist. You are really tense, is everything OK? Linda answered that she had never had an impromptu massage like this before. Well, just remember stop means stop, but don’t use it unless you are really uncomfortable. What happens on the Nauti ***** stays on the boat.

She seemed to relax a little more as I was really getting into the massage, I untied her top and continued massaging allowing my hands to slide to those magnificent breasts then back up. When I felt she was relaxed enough I placed a towel over her butt and without a word slid her bottoms down as she instinctively raised up enough to help. Now without clothing in the way I massaged her ass very deeply staying away from her private parts for now. Lifting her feet, I oiled and massaged her legs from the knee down, asking if she was feeling better…. Un Huh, immmmm.

I had brought a bed sheet up from below so I spread it out above her as I held up one side and told her to roll over… Linda did not hesitate in throwing the bikini top away and rolling over on her back as I let the sheet cover her. I removed a cold hand towel from my bucket, folded it and placed it over her eyes with just a little slit so she could peek as I said you are beginning to really relax, does it feel good? "Oh yes, it feels really nice, your so good".

Starting at her feet I massaged up her legs as far as possible then moving to her neck with plenty of oil, massaging first the left side around her breast saving the nipple for last. As I rubbed and massaged down as far as possible. I am saving “possible” for last

Moving to the end of the bench I said I was going to lift both legs and massage the kinks out as I placed her legs on my shoulder one at a time. (They never showed us this trick in school) and began massaging and moving to her thighs. Now she was letting out little moans as I saw the string.

I continued massaging at the edge of the V letting my hand move up and over the top of her mound several times feeling her quiver as I got close to her special place until finally I cupped her “possible” without waiting to hear any words like STOP. I simply asked ,good? Ummmmmmm (That was a good answer.)

As I would brush her clit Linda would arch up to try and add pressure but I wanted to control this exciting time. Finally I reached for a paper towel as I coaxed her to just relax and enjoy. Then pulling on the string, she tensed as I said just relax,,, and continued to remove her tampon and wrapped it in the towel as I replaced it with my oily finger. This time she arched up with OHHHHH as my finger entered her, turning my hand so my finger could curl upward. Searching for the waffle feeling area of her G-spot, as my finger found the place she grabbed my hand to pull it tightly to her. Waiting for this to pass I gently began to curl and rub inside with first one finger then two. Using the “come hither” curl, I was causing her to breathe faster and faster, then with my other hand I massaged her nipple until she grabbed my hand and pinched my fingers on her nipple and pulled upward far harder than I would have normally done so on my on.

This was the moment that sent her over the edge into a loud convulsing orgasm, squeezing my hand between her legs so tightly I was afraid my hand would be broken. Just as suddenly Linda fell back on the bench seat trying to catch her breath as I just kept my fingers inside her enjoying feeling the spasms subside.

As I reached for a towel to wipe my hands she shuttered at the movement, yes my hands were bloody but it wasn’t my blood and I was not about to comment. Instead I casually reached for a washrag from the warm water bucket and cleaned her special area so she would not be embarrassed. Big Boy was dripping a huge amount of pre-cum at this point…

I went back to massaging very lightly as she recovered… Reaching my stash of towels I found the condom and rolled it on Big Boy anticipating entry. As I moved on top of her I gave her a big kiss, asking if she was happy…Ummmmmm

I feel her hand around Big Boy guiding him into her most intimate wet place, who am I to argue with this damsel in distress. I ease into her feeling all the massage oils being very slippery and tantalizing. Our hips seemed to slide so comfortably together as my cock was finding a very wet & warm pussy.

Linda was looking at me with big brown eyes giving approval of our coupling. The massage oil was doing a wonderful job of keeping her from getting sore as menstrual blood can be a little gritty. I tried to last as long as I could, but her final orgasm pushed me over the edge as I relaxed on my elbows trying to catch my breath but still feel those slippery titties on my chest.

Thinking a shower was in order I got up and offered my hand as we stepped nekid out on the swim platform and enjoyed the sun and warm shower cascading down our bodies.

I used one of the large towels to dry and wrap her before I finished drying. As we sat close together on the bench I reached for her bag and without comment I found her tampon. Silently I tore open the brightly colored wrapper and pulled the plunger into position as her eyes became wide with wonder of what was happening. I put a drop of oil on the tip and asked her to open wide for Dr. Feelgood. Nervously, she complied as I opened her lips and inserted the applicator until I felt her lips on each side of my fingers, then pushing the plunger and removing the applicator I asked if I had done it correctly. Her reply was “No one has ever done that to me before, felt a little weird and exciting at the same time, but very well done” Ah well DR. Feelgood aims to please,,, always….

Sad to say I must haul anchor and get ready to pick up passengers in New Orleans, Ya wanna go along for the ride?

She sat close to me and drove the boat all the way to the marina where I took over and backed it into the slip. The guys were there to secure the lines and happy to hear the holding tank did not need pumping as they gathered up her bags and carried them to her Hummer.

In the parking lot I gave her a hug and kiss saying if ya wanna fly, be at the hangar no later than 3:30 wear dark slacks, white shirt and high heels are not advised. We will be back no later than 7 PM

I went to the office for another shower & change clothing. then pre-flight inspection of the Turbo-prop. 3:15 Linda walked into the office looking great. I took her around the aircraft for a final inspection and up the steps closing the door behind us. Nice big kiss behind the closed door, as I said follow me to the front office. Here is how you get into the right seat (stepping over the center console and sliding into the seat) , here is your seat-belts, oxygen mask if needed and a head set so we can talk to each other and you can listen to the controllers. This is a kinda sit down and watch, after we are in the air I can answer questions but for the moment it gets busy.

Although I have performed this routine a thousand times I still get out the check list to follow sequence…….Master switch on, Engine start, left then right, radios and electronics on, frequencies set along with flight path in the GPS. Call to departure for clearance which was amended to get us away from Air Force traffic and then clearance from tower to taxi.

Just before the runway final check list, I lean over for a kiss and check her seat-belts saying ya ready? Yes, wow you were busy.. Uh Huh, not bad for my first time, here hold the book on how to fly this thing…. Laughter..

(Radio call) Tower, Tango Whisky rolling, see you before 7 tonight.. Tower, have a good flight “Fox”

Throttles full, we lazily lift off, I call for Gear UP and point to a little wheel and tell her to pull back and lift up.. Following instructions the gear tucks neatly into the wings. Tower switches us to departure frequency,On course and climbing through 3000' for 21

OK now we can talk, it will hopefully be uneventful for the next hour and 15 minutes… Linda looked at me with those big brown eyes large as saucers. You do this all the time? Yep kinda routine with moments of unwanted excitement thrown in to keep you on your toes… So how did you like the dive this morning?

Silence as she stared straight ahead, for a moment I thought I had screwed the pooch asking such a loaded question but then Linda said the dive was great as she expected it would be. “The massage was unexpected but the sex was everything I had hoped it might be. I had thought about what you said at the party and realized I had been married twice, and thought I was the only girl that got horny during that time and to suddenly hear you say that was normal really took me by surprise. I found out I was not screwed up as I was told I was…. Then when I got up the courage to take you up on the diving offer I convinced myself it was just a dive lesson but secretly wishing to experience what I have been missing… you think I am a kook now I know….” Linda turned and looked out the window with her head down slightly…

I reached over and asked her to look at me.. “You are a beautiful woman that overcame the guilt from listening to other people and their ideas of what is proper. By allowing me to guide you on the path of what you were missing I am truly thankful and I would never betray your confidence. I can only hope you will think of me as a special friend to whom you can say anything without worry or being talked down to. Or you can make this a onetime thing and we can be dive buddies in the future.”

Now, would you like to fly the plane or should I keep the auto-pilot on? She replied, I have never …. I interrupted, had, period sex? She smiled & laughed saying no I have done that now and it was something I would like to do again. But what I meant was I have never flown a plane… Ah, no worries mate (in my best down under accent)

OK, put your hands on the yoke, feet on the rudder peddles follow me as I coach…. I turned the autopilot off, and showed her how the plane turns, climbs and descends…. This instrument is our course; follow the red line by making small corrections….

I never get tired of watching someone’s eyes as I take my hands away from the controls, and fold my arms… As we wing our way to LA. I make small talk about Dr. Feelgood, the wife and Special Friend which gets me a puzzled look as she seems to be saying “You have got to be kidding”

Close to New Orleans on decent, I give center a call that we have a visual for Lake Front airport. Switching frequency, the Tower clears us to land on 18… Calling the FBO on the second radio I hear a familiar voice, Crystal… ‘ Beautiful Crystal, Tango whisky,,, marry me today darling… let’s just run away….. Crystal replied “You always say that but you couldn’t survive the wedding night!” Oh but I would die a happy man…. Are my passengers there yet? Crystal replied “they called and are on their way,, be here shortly You’ll be on spot 1..” Copy Crystal, thanks-- don’t need fuel but ask the guys to help with any bags..

Gear down, three green lights, float down the long runway so I will have short taxi and pull up in front of the FBO, the guys chock the main wheels as the props stop… Inside I introduce Linda to Crystal, and hit the restroom as I hear “your PAX’s are here coming through the gate…” That is the best part of charter flights, your taxi can pull up to the aircraft, no security check, baggage check ETC.. By the time I have taken care of business the Taxi is pulling away, my three passengers are ready to board… (As I exit the office I hand my usual envelope containing 3- $20.00 bills as a tip for Crystal and line guys, that’s why I always get exceptional service)

I Introduce the passengers to Linda saying she will take the right seat (usually the co-pilot) unless “the boss” (Bryan) wants’ it. Bryan smiled, shook her hand and said no thanks, the guys and I have some confidential strategy to discuss…

Everyone is on the plane as I pull the door closed and check the locks… OK,you guys know the drill, in case of emergency pull this handle…blab bla bla. I finish the briefing they have heard before but is required by GOD and the FAA…. Linda looked like a pro sliding in the right seat up front as we all stopped and watched her cute ass go over the console..

Bryan, your scotch and ice is in it’s usual place, beer ect in the mini-bar, help yourself as I can’t afford a stewardess ha ha…. We will pull the curtain and be on headsets so you will have to tap me on the shoulder if you need anything.

I climb in the left seat, hit the master and motion for the guys to pull chocks and twirl props… Soon we are back in the air as I tell Linda I should let the autopilot or me fly the plane since we have passengers..

I mention to her that the folks in the back cannot hear what we say over the headsets unless we shout… so we talked about life in general and then she asks about “this Dr. Feelgood…”

Well years ago I discovered a desire for medical fetish or medfet. I explained how people like me were turned on by things like gyno exams, enemas, ect in a play environment and how good it felt, hence the white coat and name tag. When I mentioned enemas I saw a twinkle as her eyebrow came up. I choose that point to confide in her my like of the occasional enema from someone I trust… I followed that by asking “am I being too forward and putting you off since we have not known each other very long?”

Now it was her turn to laugh saying she “had the most sensual & sexy massage ever, you made love to me while on my period, that was a first, removed AND replaced my tampon also a first and NOW you want to know if your TOO FORWARD?,,, shit,,, that went out the window a long time ago… I felt like a virgin again and I don’t think my eyes will ever be so closed.”

Landing was uneventful, as the guys cleaned and put the plane away; I walked Linda to her H2 and of course asked when we could meet again. She looked down and said “ya know I am married and will stay that way but I have to give this some more thought…Sorry….”

I know….. don’t be sorry, Just be yourself ...

I kissed her on the cheek… Bye for now, I will never forget…