Trudy The Prude by fbailey

Trudy The Prude

My wife said, “So you want to see ‘Trudy the Prude’ in a bikini, do you?”

Naturally I said, “Yes, That’s what I just said. She is always covered from head to toe and I just know that she has a hell of a nice body under there somewhere.”

My wife said, “Well Trudy is just concerned about the sun and the effect that it has on her skin. That’s why she always wears blouses with sleeves and either pants or long skirts.”

I asked, “So what if we invited her on a vacation to someplace hot where she would have to peel some of those layers off.”

My wife laughed and said, “You would take my sister Trudy on a vacation to the Caribbean just to see her in a bikini?”

I smiled and said, “Yes.”

My wife said, “Wouldn’t it be cheaper to just pay her to undress for you?”

I looked her right in the eyes and asked, “Do you think she would?”

My wife said, “No but I could ask her.”

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A week later at dinner my wife said, “I talked to Trudy. She said that she isn’t a stripper that you can pay but that she would like to go on vacation to Antigua for a month and that she would wear nothing but bikinis if that is your desire.”

I replied, “Where to hell is Antigua?”

My wife smiled and said, “In the Caribbean you idiot. Specifically she wants to stay in Half Moon Bay in Freetown, Antigua in the West Indies. It has a stretch of pink-hued sand, craggy rock formations, and apparently very dramatic views. She said that it would be an experience that none of us would ever forget.”

I shook my head, “A whole freaking month. That’s going to cost me dearly.”

My wife smiled and asked, “Would a picture of what you are getting help any?”

Then my wife slipped a picture across the table to me. I turned it over and saw my sister-in-law in a very tiny white bikini. She was everything that I had ever imagined her to be. She had wicked boobs, a tiny waist, and long delicious legs that went on forever. When I finally found my power of speech I asked, “A whole month and her in nothing but bikinis?”

My wife smiled and said, “That’s right.”

I shook my head again and said, “Okay.”

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I decided that February would be a good month to go. I found a timeshare that I could swap one of mine for, so the accommodations were covered. I made arraignments to fly to one island, take a boat to another island, and then to take a helicopter to Half Moon Bay, Freetown, Antigua in the West Indies. Everything was all set.

Trudy told her parents and her high school that she was going. She was an excellent student and would not endanger her graduation at all.

Before the trip, my wife and sister-in-law went shopping for bikinis and went to tanning booths to get a start on their tan. They suggested that I might to get a good base before I got to the Caribbean too so I went a few times whenever I could fit it in.

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The day finally arrived, we went to the airport and checked in. I had to smile when Trudy placed a very small bag on the luggage counter. I’m sure it was a joke because my wife had packed four big suitcases and I had packed two myself.

The flight was good, the boat trip was interesting, but the helicopter ride was out of this world. We saw the island that we took off from, several other islands, and then the pilot flew around Antigua before landing in Freetown near our condo. Trudy was more excited than we were.

After getting the keys to our condo we took all of our luggage to our apartment. Trudy picked out a bedroom and went right in. Less than two minutes later she appeared. I almost had a heart attack.

Trudy was eighteen years old, she stood five feet eight inches tall, and she weighed about a hundred and twenty pounds. Twenty pounds of that had to be her tits. They were impressive, they were huge, and they stuck straight out defying gravity. That picture of her had been from the front and did not do justice to that young woman. With her height, her long brown hair to her ass, and her dark brown eyes she could pass for a native girl. Trudy not only had great tits but she had a tiny waist, nice hips, and a great ass too. She also had a dark tan and that little white bikini just glowed. As Trudy did a slow turn for me I went light headed as all of the blood in my body rushed to my cock. The first thing that I noticed was that there were no strings on her bikini. The two round patches covering her nipples must have been glued on. They barely covered her areolas. The little white triangle between her legs must have been glued there too because when she turned around there was nothing at all in the back, except for the most impressive woman in the world.

My wife is no slouch for a thirty-year-old but I married her nine years ago when Trudy was just nine years old. At thirty-six I couldn’t help but wonder if I had made a mistake and married the wrong girl.

I had to ask, “Why do you keep that fabulous body covered up all the time?”

Trudy replied, “Because I looked like this at twelve and it was very embarrassing.”

Then she added, “It’s really too bad that I have to wear a bikini all of the time…because Half Moon Bay is a clothing optional beach. I’d love to see your cock flopping around if you could ever get it to go soft that is.”

I looked down and saw the biggest bulge in my pants that I had ever seen in my life.

My wife said, “Trudy you are going to be the death of me here. He’ll fuck me till I’m raw. Thanks a lot.”

Trudy smiled and said, “You’re welcome.”

My wife took me into our bedroom, undressed, and lay herself out on our bed with her hands tucked behind her knees holding herself open for me. It was her sexually submissive position. Over the years that had become her signal that she was all mine to do with as I wished. With both of her holes exposed like that I could lick, finger, or poke whichever one I wanted too, or both of them. I was so fucking excited that I stripped and rammed my cock fully into her pussy slamming every inch of it into her. She let out a grunt but held onto her legs as I assaulted he sexually. It was not lovemaking, it was not even sex, it was raw animal lust…and it wasn’t even her that I was lusting after…and she knew it…but she took it anyway. I literally raped my own wife on that bed after seeing my sister-in-law’s flawless body.

An hour later my wife and I joined Trudy in the living room. My wife had on a real string bikini and I had on a skimpy pair of Speedo’s.

Trudy had changed into a normal string bikini saying, “I thought that the other one was too much for you.”

I asked, “Why would you think that?”

Trudy smiled, walked over to my wife, and pointed to the large red area surrounding her pussy. Trudy then said, “I think you pounded her black and blue in that hour and I counted at least five orgasms on her part.”

I looked over at my wife. She was holding up five fingers on one hand and three on the other. She then held her tender pussy for a moment and then went back into our bedroom to tie a scarf around her waist to help cover up her well-used crotch. Then we went out.

Both women drew attention but it was definitely Trudy that they were staring at. Men were walking into things, tripping and falling, and I swear one guy drooled all over himself watching her. My wife was counting bulging crotches as we walked.

We found a quaint outdoor restaurant where we sat down for a bit to eat. The waiter could hardly take his eyes off from Trudy. The food was okay and the service was exceptional. That waiter didn’t do anything else except stare at our table and to come running at the slightest opportunity.

Trudy enjoyed the attention, held her breasts up with her hands, and said, “If I had known the power that these things had, I would have shown them off years ago.”

My wife smiled and said, “That’s how I landed my husband, that and the fact that I’m terrific in bed.”

Trudy then said, “I don’t know if I’m any good in bed or not…I’m still a virgin.”

I don’t know why that surprised me but it did. You always think that the beautiful sexy girls have boys hanging all over then and trying to get in their pants. In reality I guess boys are to scared of rejection to ask the prettiest girls for a fuck.

I squeezed my wife’s knee under the table just a little and then I looked at Trudy and asked, “Would you like to know if you’re any good in bed?”

Trudy blushed and my wife stepped in, “Hey don’t knock it until you try it. He is terrific in bed and with you in nothing but bikinis this month I’ll be too worn out to handle him all by myself.”

Trudy said, “I’ll have to think about it.”

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The following day we went to Half Moon Bay. It was not the most popular beach on the island but it really did have a pink color to its sand. Some of the women were topless and some were nude so when Trudy asked if she could remove her bikini, I said yes. For some reason I felt like her father and that bothered me. I was twice her age and I guess that I could have been old enough to be her father but I didn’t want to be her father…I wanted to be her lover instead.

Trudy talked us into taking SCUBA diving lessons to become certified so that we could go out in the water deeper and see the magnificent coral and the brightly colored fish.

The classes were interesting. We had a lesson in the morning and then practiced that afternoon. Each day we learned something new and were allowed to go out further and deeper. By the end of the week we were fully certified divers.

My wife and her sister never wore anything on the beach so I opted to go nude too. I would often sport a hard-on and my wife would always try to take care of it discreetly. However, after that first week my wife finally said to Trudy, “It’s your turn. Take him behind those rocks and take care of his problem.”

Trudy smiled and took my hand as she practically ran toward that clump of rocks. We were both naked so there was nothing to slow us down. I watched as Trudy dropped on the sand and got in my wife’s submissive pose. Oh my God, was Trudy actually surrendering herself to me? Yes, she was. I remember my first fuck on the island where I attacked my poor wife. I did not want to do that to Trudy, not her first time at sex anyway, but I couldn’t help myself. I dropped down onto her like a bag of sand. Luckily my cock hit the right hole the first time and went clear in to touch her cervix and for me to knock the wind out of her. My balls caressed her exposed asshole. As I pounded down into my sister-in-law I kept pressing her body down into the sand. By the time she regained her breath I had plunged her into her first cock induced orgasm and she cried out in pleasure. I kept pounding her like that forever. She held her knees up and out keeping herself exposed to my pleasure. In exchange I rammed her constantly like a man possessed. I gave her another orgasm and another one before I finally cum in her. I pulled my cock out for a minute or two before it got hard and I shoved it back into her again. In the next hour I must have cum three times and Trudy must have orgasmed about seven times.

When we finally returned to my wife she was lying on the sand enjoying the view. She took one look at Trudy and panicked. I followed her eyes to Trudy’s crotch. She was all covered in blood. We helped her to the edge of the water and washed her off. She was chaffed pretty good and she was all scratched up…so was I. We headed back to our condo.

Once inside we headed to the master bathroom, filled the tub with water, and put Trudy in it. Upon closer examination it looked like the course sand had been responsible for most of the surface scratches and probably the internal ones too…however the bleeding wouldn’t stop. Just short of calling for an ambulance Trudy started laughing and said, “Your fucking me so hard brought on my period a few days early. It was nothing to worry about.” What a relief. What about the ocean?

Our diving instructor suggested putting in a tampon, covering that with a pad, and then wearing tight rubber shorts. It worked and we had no trouble with sharks. A few days later Trudy was okay but then my wife wore the rubber shorts.

Despite everything I had the best time of my life. I got to fuck two of the most beautiful women in the world on one of the most beautiful beaches in the world.

I traded two of my timeshares for that one in Half Moon Bay. Now every year the three of us will spend the month of February in Antigua fucking our brains out, enjoying the sand, and SCUBA diving.

And to think that it all started by me wanting to see what my sister-in-law was hiding. I’ll never call Trudy a prude again.

The End
Trudy The Prude
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