Virgin 5

"Are you sure this is how you want to spend your vacation?" my friend Claire asked. She had taken me to the airport. "You are a beautiful woman and I am sure you can find a man who would want to be with you without spending all this money."

"We've talked about this." I replied. "I am a 30-year-old virgin, Claire. I don't want to just lose it for the sake of losing it with some man who is not going to make it really good. I want it to be a complete experience. I think this is the best way for me." I gave her a quick hug and was off on my adventure.

I am not an ugly woman, in fact, I am quite attractive. I am 5'7" and I have dark blond hair that I wear shoulder length, large blue-green eyes, a small nose and a big smile. I exercise regularly and am in very good shape. My breasts are my own. I have always thought them a little too large at 34 D, but that's what I have been given and I accept that.

My mother and grandmother raised me and I went to all-girl schools throughout my education, including college. I have a job that I love that keeps me comfortable financially but work mainly around women. I don't get a lot of opportunity to meet men and, when I do, I don't know how to act socially. I don't know how to attract men. I have been out on a few dates but found it awkward, so have since avoided it. I am not sexually attracted to women: my life has been chaste.

I had found a site on the Internet about a resort for women to have their sexual fantasies fulfilled and I had explored it and researched it for the past year. As a birthday present to myself I had decided to try it. I had followed all the instructions, I was on the pill and I could always back out at anytime. As I was a virgin, I had been sent a kit of dildos in varied sizes to insert into myself so that I would be stretched. I had found this exciting and had even made myself cum on a few occasions. I knew that after this experience I would use them on a regular basis. The resort was close to home: an island in the San Juan's.

This was a very thought out decision, just like I have lived my life. I was going to the resort a virgin and would come away from the experience a completed woman.

I arrived at the Seattle airport and there was a tall handsome blonde man dressed casually with a sign that had my name on it. When I approached, he looked a little surprised.

"Hi, I think you are looking for me." I said. He asked to see my ID and reservation ticket.

"Come right this way." We got my luggage and then went to a black BMW. "Please join me in the front seat" he said. He opened the car door for me and helped me in.

As we were driving to the ferry, he said, "I have read your profile and am surprised. I wasn't expecting someone that looks like you." I smiled and asked him what he had expected. "Oh, I don't know. Your picture was just a face. I guess I was expecting someone without as much self confidence".

"So you know my story? I am very nervous about all of this." I said.

He smiled, "Don't worry. This is going to be fun for you and us."

"Us?"

"Yeah, you will have four men to make your fantasy come true. I am one of yours."

"Oh," I replied with some concern.

To make me feel more comfortable he started talking about the resort and the island. The time flew and we soon arrived. There it was: a rambling wood structure with multiple wings nestled in a grove of old growth cedar.

"Lets get you settled," he said.

He took my luggage in through the entry and then we went through a large door. "This is your wing. You will not see the lobby again until you leave at the end of your time with us."

We entered my wing. There was a great room with all the amenities: a large rock fireplace with comfortable couches around it and a wide-open space with a tub by the windows over looking the ocean.

"The sleeping area is in the loft. Lets go unpack for you." He took my luggage up. There was a huge bed with a view of the ocean. It was covered all in white.

"That is in honor of this being your first time," he said as he ran his hand down my back. The walls and ceiling were all mirrors and I could see myself at every angle. Alex opened my suitcase and looked through it. "I don't think you will be needing any of this," he said as he put it in the cupboard.

"Now let me help you get more comfortable before you meet the rest of the guys." He slowly began undressing me. I had to remind myself that this is what I paid for as a hot blush crawled up my skin. He was looking at me so intently and touching me gently as he first unzipped my dress and slid it off of my arms. He turned me towards the mirrored wall.

"Watch while I undress you. Look at yourself. You have a beautiful body," he said as I watched him run his hands down my sides. He unfastened my bra, slid it off and let it fall to the floor. While standing behind me, he gently cupped my breasts in his hands and ran his fingers over my nipples.

"You've never had a man do this before, have you? Look how hard your nipples are getting when I roll them in my fingers." I could feel a tug down to my mound. He then reached down and pulled my panty hose and panties off until I was standing naked in front of the mirror. He ran his hands from my breasts down to my hips and pressed himself against my back. I could feel that he was hard.

"This is going to be so much easier than I thought. Can you feel how hard I am in anticipation of fulfilling your fantasy? " He pressed himself more firmly against me and touching the hair on my mound. "I hope you are getting wet thinking about what is going to happen to you."

He helped me put on a white satin robe then took me downstairs. There were three men sitting on the couch. "Guys, I want you to meet Lynn. She is our pleasure." He untied the robe, opened it and let it slide to the floor. I was standing naked in front of four very attractive men. I felt the blush start at my neck and worked its way up my face and down to my breasts. I was so very nervous. I had never had one man see me nude, let alone four.

"You can remember us by the letters of the alphabet: I am Alex, your main guide and this is Ben, Charles and Dave. We have never had a virgin before." They were all smiling at me.

"We are going to start by helping you to relax. Lets go to the bath first."

Everyone rose and I was led to a soaking tub large enough for all of us. Alex helped me in.

"Sit right there while we undress for you." They each undressed in turn until they were only wearing thongs that just covered their manhood. My mouth went dry.

"We are going to take this slow for you, but not too slow because we want you to get the benefit of your time with us." They all came into the water with me and washed my body. They ran their hands over me and then lifted me out and placed me on a table by the side of the pool.

"We will start by giving you a massage and shaving you in preparation for taking you: we want to see all of you." Alex said. "There is trust in bondage, Lynn. We want you to know you can trust us," He said as he put a blindfold over my eyes so that I could not anticipate what was coming next. They gently tied me to the table. The table was electric and separated into segments to support each part of my body. The arms and legs could be moved in any direction. It was covered in a very soft fabric that felt like silk against my skin. I felt hands on my head as someone gently began massaging the tightness in my scalp and neck, and my feet and legs were each being massaged by different hands. The legs of the table slowly separated until I could feel myself spread.

"I am going to shave you now, Lynn. You will feel me touch you. Have you ever had a man touch you here before?" Alex asked.

"No" I replied.

"I am so happy to be the first, Lynn." I could feel something warm being spread over my pudenda and a hand running over my mound and down between the cheeks of my bottom. Slowly he spread the shaving gel, it was warming and he was so gentle. I felt hands going to each of my breasts as they, too, were being massaged.

"It is very important for you to hold still while I do this. Relax."

So easy for him to say, I thought, as the sensation of having my breasts stroked and my mound touched at the same time unnerved me. I could feel the razor slowly start at the top of my mound and pull the hair away. Then down the sides of my lips and around the crack of my bottom. Then I felt him lift one of my lips and shave the inside so close to my button.

"That no man has ever touched you before is making me very hot, Lynn." he said as he continued to shave me. The warmth felt so good as did his fingers touching me. I could feel warm water rinsing me as he removed all of my hair and the shaving cream. He ran his fingers down the inside of my lips and back up, never touching my button. "You are so smooth. You feel wonderful."

"What would you like us to do next, Lynn?" Alex said, as I felt warm mouths sucking on my breasts and his fingers lightly stroking me. "Can I taste you, Lynn?" My body was tingling and hot from their administrations.

"Oh, Please!" I then felt a warm tongue on the side of my lips. Up and down my slit, not touching my button, just circles around it and lips sucking each of my labia into a warm and wet mouth. My body involuntarily arched into his face as he slowly licked me.

My body was being touched all over, my nipples and breasts were being licked and sucked; I was feeling a sensuality like I had never experienced before. Finally his tongue found my clit and I moaned with the pleasure of it. He sucked with his lips and his tongue flicked over my hot button, over and over again. The tug inside of me was amazing as they all continued to touch my body. I could feel the pressure build as my muscles tightened and my whole womanhood was ready to explode in my first man-made orgasm. I could feel my skin twitch, expand and contract as I moaned. He did not let up on sucking me and it became almost painful as my orgasm spread over me, the pleasure was so intense.

"Oh, Lynn, that was wonderful. We are all going to have so much fun!" Alex said as Dave removed my blindfold. I was lying there with eight hands on my body, knowing these men had watched me cum. I was untied from the table.

"You are so wet, Lynn. Feel yourself." Ben said as he moved my hand down to my mound. "Put your fingers there and feel how wet you are. Yes, like that, now rub them back and forth...I am going to be the first to enter you and you need to be very wet for me. We need to do this now, so that you can experience everything. We don't want you too sore, but you will be," he said with a smile. He removed his thong and his shaft was long and wide and very erect. I was a little frightened, I knew that if I said to stop at anytime, they would, but I would be taken back to Seattle and sent home: it was part of the contract.

Ben took me by the hand and led me up to the bedroom. The others followed. "We will all be with you the whole time, so just relax."

I lay down on the bed with my head in Alex's lap and my hips at the bottom edge and Charles and Dave sat at each side. They placed pillows under my lower back so my hips were elevated to the level of Ben's waist. Alex bent over and kissed and stroked my face, while Charles and Dave each lifted one of my legs up until I was spread for Ben. They each stroked one of my breasts. Ben walked up to me.

"This seems almost clinical doesn't it, Lynn?" He said. He positioned a large warm light on my mound so that I could see myself in the mirrors. "See how much I want you?" he said as he showed me his hard, hard, rod. He rubbed the head of his large shaft up and down my slit to make it very moist and then placed it at the entrance to my virgin hole.

"Did you use the dildo's as you were instructed, Lynn?" he asked. His finger found my button and slowly made circles on it as he slowly pushed his tip into me.

"Watch it go into you, Lynn" Alex said. "This is your first time, relax, now." It was so hard to relax as they all were touching me and I felt so in need. I arched towards Ben as he played with my button. I again felt the building of a climax approaching.

"Okay, I am going in now, Lynn. Feel me enter you." He pushed himself in until his head was in me. He was much wider than the dildos I had been given. It felt so tight and he groaned and seemed to grow larger.

"We still wanted you to have the virgin experience, Lynn. That is why we gave you smaller dildos then our cocks. But we also wanted you to experience the true loss of your virginity." He pulled out and pushed again, a little more each time until we both felt him stretch me as wide as I had ever been. He pulled out and put his finger in and gently stretched me, using circles to open me up more.

"Oh, you beautiful woman, it will hurt some, but you are so wet. I am going to go back in and push through and then just wait inside you until you're ready for more" he said.

He again positioned the head of his shaft at my entryway and pushed in. I could feel myself stretched beyond my limit and I arched into him hard as the other three held me. They caressed my body as Ben sunk his shaft all the way into me with a moan of extreme pleasure.

"You are so tight and so warm and so wet. Are you ready for me to keep going?"

"Yes, oh yes, don't stop, please don't stop" I rasped, as he began to pull back and then push in again. Dave and Charles started playing with my clit as Alex sucked on my nipples and Ben pumped into me. I could feel another climax building and Ben started going faster and faster. I could feel myself move over the hard skin of his tool as he pumped his hips into me. The feeling was so much more intense having a real man and not a dildo in my virgin hole that I again had a crashing orgasm and felt Ben's cum rush into me. He was just as turned on as I was.

"Keep going guys, you next, Dave" said Alex as Ben and Dave changed places.

Dave entered me quickly. He was longer than Ben and I could feel him all the way inside as he pumped his hips in circles around and around, stretching me more and more with each thrust. I came again and then I could feel him cum, too. Charles was up and poised over me just as Dave pumped his raging orgasmic load into me. He entered me in one hard stroke and he was so thick it felt like I was being opened to the limit. I could feel all of the cum that had been shot into me run down the crack of my bottom. Ben moved to my head as Charles pumped into me hard. I was moaning and arching, feeling more animal than woman as I came again.

Last it was Alex's turn. He went very slow and pushed the head of his penis into me and then out, teasing me. "I want you to climb my pole, Lynn. I want you to want it more than anything." I was so tired, and I had cum so many more times than I was use to that it was very difficult, and then I felt a finger go into my back door and I raised up onto Alex's long shaft and I was being entered in both my holes at the same time! It felt so good I lost myself to just being a sexual being and I climbed his pole over and over again until I came again.

"You're not a virgin, any more, Lynn." Charles said. "You have much more to experience and we are all excited to teach you." I was so satiated that I did not know what could possibly be better. I dozed, definitely looking forward to the next few days.

I slowly awakened, feeling someone touching my hair and so very hot. The dreams I had been having were very sensual and of having someone inside of me. I stretched and remembered what had happened to me just hours before and was surprised to feel a coolness between my legs. I opened my eyes and could see the glow of the pink and orange clouds shimmered off the water around the island. It must be sunset. I looked up and saw Dave. His black hair reflected the light from the window and his golden skin was beautiful.

"It's time to wake up, Lynn," he said while he smiled at me and brushed my hair. "We have much planned for you this evening and we need to feed you."

I stretched and could feel something between my legs - it was very cool and made me feel very full. I looked down. There was something inside of me. Dave laughed. "We have been keeping you cool down there." He reached down and pulled a dildo out of me. "We didn't want you to be too sore so we have been keeping you cool while you slept. Here, let me put a different one in you."

He went to the small refrigerator and took out a large yellow latex dildo, much larger than the one he had just removed. He put it in his mouth and covered it with saliva and then came over to me and spread my legs and gently started pushing it in. The feeling of it sliding into me was like a very large, cold cock but it went smoothly in with his saliva and the wetness from me. I could not believe how wet I was, I could feel it between my legs and down my crack. He smiled and slowly pulled it out and pushed it in until I found myself wanting to be fucked once again.

Alex walked in with a basin of water. "Let's clean you up before we feed you, my love." He sat the basin down and took a washcloth and washed my face very gently. Around my eyes and over my cheeks and behind my ears the cool cloth circled. It was almost as sensual as being touched in more intimate places. He reached over and placed a kiss on my nose. "I bet the last time someone washed you was your mother. I promise this will be nothing like what she did."

He washed down my neck and reached my breasts. He washed the top and then lifted their heaviness and washed under them. He grabbed my nipples with the cloth and rubbed them until they stood high and hard. He left them damp and softly blew on them to make then dry, sending pulsations down to my pelvis and I could feel it begin to engorge with blood again.

As he finished each part of my body, he would kiss me and then Dave applied a scented body lotion, gently rubbing it into my skin. He also paid special attention to my breasts and my large nipples, twirling them between his fingers and I could feel my vagina spasm around the cool dildo. Alex continued to wash me - my stomach, my legs and my feet.

"Lets roll you over and get your back, too." He and Dave rolled me over as they washed my back and applied the lotion. Alex washed down my crack, washing into my hole and Dave oiled it, reaching inside to make me groan. "Come on now, into the bathroom." Dave pulled the cool dildo out of me and they walked with me to the bathroom.

"We have a bidet." The water temperature was just lukewarm and Dave washed me and sprayed the water over and into my perineum, using his hand to make sure all the soap was washed off. He then oiled it, just as he had oiled my other hole, reaching deep inside.

"You really don't need this, do you? You are so very wet on your own". He pulled out something that looked like a large cotter pin: it was made of stainless steel and was inlaid with ebony stripes. It had two long stems that looped at the ends; they formed an open loop at the top.

"Here, I am going to slip this over you. He bent down and slowly sucked on my clit until it was hard and then slipped the long ends over my inside lips, with the top loop holding my clit up.

"This jewelry looks wonderful on you. It will keep you hard, just as a cock ring will keep me hard. Do you know what a cock ring is like?" Of course I had an idea but had never seen one. He smiled. "We have lots of toys we are going to share with you and help you enjoy and then you will take them home with you to enjoy there."

"Tonight you are going to learn how to suck a man. We will not enter you with our cocks again until tomorrow. Tonight we will teach you what a man enjoys and how to make him cum with your lips and tongue and teeth, just as we will make you cum with ours. Now it is dinner time."