Wor Buddies

The next day I entered the office and Jenny and Carmen were deep into conversation I said Hello and got smiles and knowing glances from Carmen all day. I didn't ask Jenny not to say anything to others I just assumed her silence since there was an office policy about office relationships.

Carmen was a throwback to the 60's. She was about 5'5" and weighed about 105 lbs. with bleach blond shoulder length hair, her typical choice of clothing was a designer t-shirt and floor length skirt and sandals. Today I noticed for the first time that Carmen did not have anything on under her t-shirt because her nipples were fully erect.

Carmen is what I call a clinger. She does this with almost everyone if you are sitting, she comes up behind you, leans her left arm on you right shoulder and plasters her body up against you. Someone who didn't know her very well you would think she were throwing herself at you. Today though it was different, today instead of just standing there she began to ever so gently slide up and down rubbing her small but very perky tits against my back.

All day long I kept trying not to stare at her, but it was difficult, as she would cross the office I would absent mindedly watch her walking, then we would make eye contact smile. Then that awkward moment would occur where you look at a spot on the wall like it's the most important spot in the world. At that very moment it was. Carmen would just grin and keep going. This went on for most of the day, the problem for me was, I was becoming aroused and it was getting uncomfortable for me, as well as, embarrassing when I would stand up.

I was glad that this was my early day since I closed the night before. I knew that Carmen wasn't really flirting with me because she was getting married in just a few weeks. It had to be that my mind was stuck on sex since what happened last night. As I was leaving I stopped by jenny's desk in the reception area and left her a note since there always seemed to be patients around her area. The note said "I am staying on my sailboat tonight come to Jackson Park Harbor we will take it out for a sunset sail" I saw her take a quick look at the note and stick it into her pocket with a smile. Leading me to believe I was in for an encore of last night.

I got to my boat which was moored to a can out in the harbor and brought it along the dock. I changed from work clothes to shorts and a t-shirt and proceeded to prepare my boat for what I thought would be an evening of love making. An hour later, no Jenny and it was only about a ten-minute walk from our office in Hyde Park to the harbor, her shift ended 30 min ago. I was just about to give up hope for some female companionship and take my boat out for a sail and clear my head. I was thinking what was going through my mind, I was not the kind of guy who woman threw themselves at what happened last night was a fluke never to happen again. Just then I hear a female calling my name, my heart began to race thinking it was Jenny, but when I looked around it was Carmen instead of Jenny.

Carmen came trotting over with a big smile on her face and asked if she could go instead of Jenny, since she had to study for a college test the next day.

I said sure come aboard. As Carmen stepped from the dock onto the boat she caught the hem of her dress and fell into me. In the excitement of the fall my right hand caught her left breast. I could feel the surge of electricity between us and her nipple become hard under my palm. I probably left my hand there a little longer than I should have since there seem to be another awkward moment immediately after that.

Once she got her sea legs it became obvious a floor length dress was just too dangerous on a sail boat so I told her to go below to my cabin and change into a pair of gym shorts from the drawers on the right. Carmen went below while I proceeded to shove off and motor out of harbor. We were just leaving the mouth of the harbor when Carmen came from the cabin; she changed from her long dress and silk t-shirt to a pair of my boxers and one of my tank top t-shirts.

She said that she changed shirts as well since she was afraid that the spray from the boat could ruin her silk shirt.

I told her what ever made her comfortable. It rapidly became apparent that the clothing that she chose was significantly big on her. With every breeze her shirt would inflate and completely expose her small pert breasts with half dollar size nipples fully erect.

The boxers she chose even though they were new were three sizes too big for her. The waist band would ride low on her hips showing off her flat stomach and the creases of the front of her hips stopping just inches above her pussy. I wasn't sure but I thought I could see a tuft of dark hair peeking out over the top o the waist band.

I had Carmen hold the rudder still, on a course slightly off of directly into the wind, while I set the sails. As I raised the main sail the boat began to accelerate with a surge of power from the sail.

Carmen not having been on a sail boat before became nervous and pulled the tiller catching even more wind and accelerating even more.

I had just finished un furling the genoa sail the boat began to heel over to about 50 degrees not dangerous but if you don't know this it feel like the boat is turning over.

Carmen is screaming for me to come back. As I reached the cockpit area I noticed her on the lower side of the boat getting sprayed each time the bow of the boat struck a wave. The T-top was flapping in the wind and the white cotton boxers were becoming transparent.

I took the tiller from her and helped her to the high side which was much dryer.

She realized how little the top was concealing and asked if it would be OK for her to just take it off. The top it was more of a nuisance than anything else.

I said sure we were about a half mile off shore of Lake Michigan heading out. I did not want to seem like a letch staring at a friend almost naked body knowing I would be attending her wedding in a week or so. I could almost control my eyes but another part of my body had other ideas to the point of embarrassment.

As Carmen returned I had moved to a standing position on the side bench so I could better see what was in front of the boat. The boat lurched and she lost her balance and started to fall. She reached out to me and caught me at my waist with her hand firmly grabbing hold of my very erect penis she held on for a lot longer than was necessary and with a smile on her face she said now we were even.

We settled in for a nice smooth sail sitting close to each other cheek to cheek as you would say because as the sun began to set it started to get cooler.

Carmen's nipples were becoming fully erect with the cool breeze on them which in turn was having an effect on me. I put my arm around her which was welcome for the warmth. My hand absent mindedly came to rest on her right breast her nipple lightly brushing the palm of m hand with that touch she took a deep breath and raised her breast firmly into my hand. My fingers instinctively began to caress her breast and nipple. A low moan came from Carmen as she responded to the rhythm of my caress along with the natural rhythm of the boat.

Carmen turned, looked into my eyes and without saying a word parted her lips and we kissed. I at first tentatively dipped my tongue into her mouth and reached the tip of her playfully toying with each other. I gradually began to withdraw teasing her tongue into my mouth then sucking her into a deep kiss.

We broke from kissing just long enough to set a course on the auto-helm and attach it to the tiller. Now my hands were free and I was able to explore Carmen's body. We resumed kissing as my hands played with each of her breasts.

Carmen responded with moans and arching of her back pushing her breasts firmly into my hands. Her hands were not idle during all this, she managed to unbutton my shorts, opened my fly and slid her small delicate hand down my member giving it a gentle squeeze.

I remember how her small hand made my 6-inch penis look larger. This action spurred me on to investigate what lied beneath those boxers. I slid my thumbs inside the waist band of her boxers and began to slide them down off her hips. Carmen sat upright and put both her hands on my chest and pushed us apart. I thought; oh no I had gone too far and pissed her off.

Then Carmen said whatever happens on this boat stays on this boat, I am getting married in a week and a half and I love Roger. With that said, I grasped the sides of her shorts and pulled them to the floor.

I placed my hands on her hips and pulled her belly towards my face as I sat with her standing in front of me in front of me. I began to start a chain of kisses the started at her navel and progressed down to the left crest of her hip. I continued down that delicate cease between her belly and thigh Carmen began to moan and roll her hips. I slid my left hand between her legs and slowly caressing her inner thigh until I brushed the outer lips of her pussy.

She was dripping wet; Carmen placed her left foot on the bench next to me affording me easier access to her. I placed my right hand around her backside and grasped a handful of he left buttocks while my tongue and left hand explored the cleft of her mound. Her pussy was clean shaven with the exception of a patch of dark hair shaped like a hart.

I had Carmen sit on the bench with her back against the cabin wall I placed her left ankle on my right shoulder and began kissing her ankle working my way down her lower leg to her thigh until I reached her pussy and parted her lips placing light touch kisses.

I eventually reached her pink opening and slipped my tongue in as deep as I could, taking time to suck and toy with her clit. I moved the hood back with my lips exposing a small glistening tip that when I sucked it, Carmen exploded into an orgasm that shook her entire body.

After a few minutes Carmen had me lean back and raise my hips so she could remove my shorts. She kissed the tip of my penis. Then rolled her tongue around the head, while she massaged my testicles. She slowly began to slide her mouth over the head of my penis and down the shaft, about two thirds the way down she would gag and pull back and try again within a few seconds. I could feel the head of my penis reach the back of her throat. and my organism was becoming eminent. I came in hard spurt after spurt until cum was leaking from the sides of her mouth. Carmen licked me clean and with her finger caught the dribble that leaked out the sides of her mouth swallowing it all.

For about 15 minutes we gust laid there caressing each other as Carmen's caresses focused on my penis I started to become excited again. I changed our position so that I was now kneeling on the floor of the cockpit with Carmen sitting on the bench with both her ankles on my shoulders. I started to rub my cock the length of her pussy causing her to become very excited and wet. I positioned the head of my cock at the opening of her vagina and slide the head of my cock past her Labia when she screamed NO! I was afraid I had hurt her and withdrew before I had a chance to penetrate her.

Carmen was sobbing at this time when I asked her what's wrong she told me that her and Rodger had never gone this far and she had never been with another man before that she was still a virgin. She said that she wanted to save that for her wedding night but she did not just leave me hanging. She said this night was the most sexually stimulating night in her young 22 years and wanted to bring me to completion, not only for me but for her.

I hugged her and said Rodger was a lucky guy. Then I started to chuckle she said what's so funny thinking I was teasing her but in reality, it had occurred to me that there still was one other orifice that we had not considered yet!

At first Carmen look at me with a puzzled look on her face then all the sudden her mouth dropped open in shock. She said "you mean back door don't you". I got this chasseur cat smile on my face "I have never had anything go in before just out. Will it hurt?"

I told her in a week she will be married that she should try as many things as possible before the big day (hoping to convince her with this lame excuse).

She shocked the shit out of me when she said "OK" I took her below deck we laid a beach towel across the table for padding.

I had Carmen bend over the table which created a perfect entry target I grabbed some KY from my cabin and lubed up my cock then I placed some on my finger. I placed my finger against her little brown button and slowly made little circles around her anus until the sphincter muscle relaxed and allowed the tip to penetrate.

Once I got one finger in and kept massaging the opening until I was able to insert a second finger when the second finger entered her Carmen let out a low moan and she started to push back against my fingers in a rhythm to match my massages.

I applied more KY to her anus and placed the head of my cock at the opening. I could feel the opening pulsating and timed my penetration of this other virginal opening. With the entry of the head of my penis her muscles tensed. I thought she was going to pinch it off or crush the head but she relaxed and the pressure subsided with every centimeter I entered she would either moan of take a deep breath. I was about half of my length in her when I told her to take a deep breath and blow it out. As she did I pushed the rest of the way in and held myself there until she adjusted to the fullness.

Once she recovered from that I began to rock in and out slowly build speed increasing how far I pulled out and pushed back in. Soon I was pounding as fast and as hard as I could Carmen was only repeating three words at this time "OH MY GOD".

All the sudden she arched her back and breathing quickly all this time she was massaging her clit vaginal fluids were running down the insides of both legs. As she reached climax so did I baring deep inside her several spurts of cum, enough so that it was leaking out as I pumped away. As I slid out so did some of my cum mingling with her fluids running down her leg.

I grabbed a towel and proceeded to clean Carmen up as well as myself. I laid her on the bunk and went topside to see where we were. I changed course and set sail for home when I came back down Carmen was a sleep so I placed a blanket over her and returned to the helm.

The entire cruise took 3 hours. I couldn't help thinking what had changed in my life that brought all this about? First Jenny then Carmen what got them so interested in me? Carmen woke from her nap and came out to the cockpit draped in the blanket I covered her with.

Carmen sat next to me started to speak, then just put her head in her hands rubbing her eyes. I placed my arm across her shoulder and held her tightly. She kept mumbling that she was getting married in just under two weeks. I reminded her that she stopped me from taking her cherry that she saved that honor for her Rodger.

I told her that I had always thought of her as a friend and hoped that we would remain friends moving forward. That we both got caught up in the moment. Don't let this moment in time destroy her future with Rodger. I will always cherish what we did tonight, and if her and Rodger were to ever break up I would be knocking at her door. She looks up to me smiled, then dropped the blanket, jumped up and gave me a huge hug.

The next morning at work as I was getting my first cup of coffee, Diane one of the other Physical Therapist saddles up next to me and says out of the blue "Are you ever going to ask me out on your boat?"

I just stood there with my mouth open in shock. She just stared me in the eyes waiting for an answer. I tried to pull myself together and responded. I did not know if she knew about what happened out on the boat with Carmen last night. So, I replied with anytime you want, I pretty much live aboard my boat during the summer.

She turned and smiled and said "I will tell my husband we can all go this Saturday" as she walked away.