Not the Way I Planned It

Traci and I had our business and our social life which were both very important to us. Our sexual adventures had taken us to exciting heights. Traci had convinced me that much of our hang-ups come from conditioned responses of our early lives. It was not that we detested society and rules; it was that she believed in reality instead of pretense. Much of her conclusions were drawn from her upbringing just as mine were. We shared a childhood of instruction, reward and punishment. However, there was one major distinction. Traci was outside the box and wanted to examine each restriction for its own merit. I am more black and white and rules oriented. It must be the physiological makeup and left brain vs. right brain thinking.

Initially I was hurt and threatened by her different outlook on life. After our relationship grew into a marriage, I began changing some of my perspective. Having a wonderful sex life seemed to do wonders for my acceptance of new ideas.

It seemed that after we reached a new plateau sexually, we always returned to the subject of my well below average cock. I was excited thinking about Traci taking a huge cock into her mouth and pussy, but I was still worried about losing her.

We had reached the point where dildo play was the new high. I was blown away by her transitioning from me fucking her with our big brown dildo to her fucking me with a strapon. We did variations of these games maybe once a week. Weekends were more adventuresome because we had more time to devote. We worked hard and sex was more vanilla during the week. Not that we did not enjoy it. It was just that quickie sex was like eating vegetables where kinky sex was like having desert.

Increasing the intensity of our dildo play, Traci led me to a new experience almost every time we "kinked out'. That became our little code word for variant sex.

One Friday evening, we went to dinner with some neighbors. Traci was very flirty with everyone. Even some of the girls asked her if she had over indulged in the drinks. It was noticeable to everyone. She touched me most of the night and even stole some feels of my cock. I was hard most of the evening. I guess that is one benefit of having a small cock. Imagine trying to hide a ten inch erection while eating dinner.

We got home around ten o'clock. I asked her why she was so hyped up this evening. She said, "I don't know. It has been awhile and I think I will fuck me some boy pussy tonight."

She directed me to the shower. By now, I kept my genitals and body completely hairless at all times. I took a shower and dried off. When I came out of the bedroom naked, Traci was waiting for me. She told me to sit down. She then proceeded to take a pair of her sheer white stockings and handed them to me. She said, "Put those on carefully. I am going to take a quick shower and get dressed. By the way don't put any runs in my stockings.

I had not noticed at first, but she had draped our entire bed with a plastic drop cloth. She had taped the corners and then lay several bath towels across the bottom half of the bed.

I questioned wearing the stockings, but I had worn her panty lace belt several times when she had fucked me with our little dildo. I carefully started gathering the stockings up into a ball as I had seen Traci do hundreds of times. I slipped one stocking over my foot and up my leg. The tops were elastic and they stayed up on my thighs. I placed the other stocking on my other leg and then admired myself in the full length mirror. I had never thought about this before, but now all shaved and in the sheer stockings, I concluded that my legs looked pretty good for a guy. I was a little surprised by this.

She came out of the bathroom in all pink. Her eye shadow was even pink against the normal eye shadow and liner she had worn to dinner. It was amazing what a little enhancement can do to the overall picture. She wore a pink bra with only half cups. Her breasts stood high on her chest and her areolas appeared to have a little pink makeup blush applied. I also noticed a little bust makeup that seemed to accentuate the cleavage and rise of her already gorgeous breasts. She had on pink stockings and 6" pink stilettos. Her panties were a shiny hot pink thong. The panties were mostly obscured by her cock harness. I could not believe she actually found a pink harness. But her cock was new also. It was about two inches longer and considerably thicker than my small starter dildo.

She pranced around in front of me and complimented me on my stockings. Just then she seemed to have an idea. She took out one of her garter belts and helped me put it on. She attached the garter straps to stockings. She went over to the nightstand and took out the Astro Glide. She looked at me and came back. She pulled me up from my seat on the bed and embraced me fully. Her cock came between us and bumped into my stiff little erection. She giggled and stepped back.

She held my cock in her left hand while holding her dildo in her right hand. Gently, she eased me back to the bed on my back. I lay back on the cushion of towels while she poured the lubricant into her hand. She transferred the Astro Glide to my waiting bud and probed her fingers in and out to lube me up good. She then rubbed the lubricant liberally on her pink cock. She slowly worked her hands over the cock and I noticed now that her nails were pink also.

She leaned forward just so that she was able to remain standing in her slutty heels. She pulled my legs up tilting my ass up slightly. Slowly, she brought the pink dildo near my asshole. Gently the head made its way into my rectum. I had learned to relax easily so there was no harsh pain that I had experience the first few times. Thrusting ever forward, she sunk the larger cock into my stretched hole. The sensation was fuller and more erotic than ever.

When she had fully entered me and began stroking in and out, she reached her hand and encircled my hard little cock. The lubricant was still on her fingers and hand and it slicked up my cock. Also, I was generating a copious amount of precum. This, mixed with the lubricant put a slick film on my cock.

"You like that, Boy Bitch?"

"Oh, yes, yes."

"You know that this little dicklet could never satisfy a woman, don't you, Baby?"

"I know, Honey, but I can fuck you with our big friend and eat your pussy."

"Yes you can, but I really miss a big real cock to suck and fuck."

"I think it is time you gave me a big cock cowboy to show your appreciation for my sex instruction. Don't you?"

She started sliding her hand up and down my little cock.

"You like this, Baby?"

"Oh, god , I do."

"So how about a big cock for Traci?"

"I love our dildos and I love fucking your ass, but I need a big cock and I have waited long enough. I don't want a boyfriend, a just want a big cock to fuck me."

I was sweating cold. But the sensation was overwhelming. The extra length and girth of the dildo was filling me up so much. Her hand jacking me off felt so good that I could not stop.

"How about it Terry? We are going on vacation next month. Can I have a big cock to please me? Please. You can watch and help. OKAY?"

"Please. I love you."

I was in convulsions. My body tensed and knotted up totally. I felt a huge orgasm building. She stopped moving her hand and stopped fucking me with her pink cock.

"OK."

"OK what, Terry?"

"Oh, oh, OK, you can fuck a bigger cock."

"Thanks, Terry. Now lay back and enjoy the ride."

She leaned her whole body against me and pushed her cock so far up my ass I thought I would faint. Her hand encircled my hard cock. I started cumming immediately. She held my cock and directed the bursts at my face.

"Fuck, Terry, open your mouth."

I did and immediately a large rope splashed into my mouth and nose. The next one hit me in the right eye and onto my forehead. Another spasm and I shot all over my hair and back onto the bedding. Several more streams exploded straight up and rained back onto both of us. As they got smaller and less explosive, she directed the cum onto my belly. It pooled there and everywhere else. She began rubbing her hand in the cum pool and slowly stroked ever last drop out and onto the head. It then ran down my softening cock as she continued to massage it.

She dipped her fingers in my cum and sucked them. She dipped some more and fed it to me. She rubbed my cum all over my body. There was plenty. Traci then stood up and removed her bra and laid her full breasts on my chest. She squished and slid on my cum and licked it off my face. She dipped some of it into her mouth and fed it back to me.

When she rolled over on the towels and we started getting our breath back, she asked, "Are you certain you don't mind if I fuck a really big cock every now and then? You will be there always and nothing behind your back will ever happen."

"By the way you legs look great in my stockings. I am a little jealous."

She giggled and kissed me on my cum covered lips.

Over the next month we worked very hard to get our business in shape so we could enjoy our vacation. During our love making, Traci continued to re-enforce my commitment to letting her enjoy a big cock. We were going to an adult vacation spot in Jamaica. We had heard that this was one of the hottest places to go. We were planning plenty of activities and adventures, but we left plenty of time on the schedule in case we had an opportunity to pursue her goal.

Several days before we were scheduled to leave, Traci told me to get cleaned up after dinner. I knew we were going to have sex and since she told me to go clean up, I knew to take the enemas. I was not surprised when I saw the stockings laid out near my hygiene items. I was surprised to see a hot little lingerie item. It looked to be what was called sissy panties, but the bottom panty of this pair had been cut away leaving a ruffled lace skirt. I put on the stockings and the skirt and admired myself in the mirror. The lacy skirt rubbed up against my hard little cock making me more excited with every swish.

When I came out, I saw Traci standing there in a sexy outfit with platform stilettos, white garter belt and sheer stockings. Her harness held the largest of my anal dildos. She had almost stopped using the small one on me. She had me turn around to see how I looked in my skirt and stockings. She told me we had a few changes for this session.

First, she pulled out the small dildo and placed it in her mouth. Then she offered it to me. I thought that she wanted me to do the same. She pressed it to my lips and encouraged me to suck it. I reluctantly obeyed her. She slid the cock further into my mouth until the tip was on the back of my tongue. She then slid it out and placed in on the nightstand. Next she took the large chocolate dildo. She swirled her tongue around the head, then slowly started pushing it into her pretty lips. Deeper she went until I thought she would choke. But she did not choke. She pushed the big cock ever so slowly until it disappeared all the way to the balls. She pulled it out finally. She licked the head again and pushed it down her throat again.

Next she pulled it out and offered the head to my lips. She did not allow me to pull back and inserted the head into my mouth. She continued to push until I began gagging. She pulled it quickly back as I coughed out saliva. Traci giggled and seemed happy that she had finally demonstrated her deepthroat talent. After she had used it on my mouth, I had a new appreciation for the art of deepthroating.

She laid me down on the bed and gave me a very wet blowjob. I came in her mouth and she swallowed my huge load. I thought this was unusual. Normally she would hold it in her mouth and snowball part of it back to me.

However, as soon as she finished, she laid me back on the bed and lifted my skirt. My cock was spent and very soft. She produced a pink chastity device that clamped around my balls and attached to the head. The pieces locked together and were secured with a small padlock. It was uncomfortable having this placed on my cock and the ring around my testicles was very tight. I soon found out that even my little cock could not get hard in this device.

Traci explained that if we found a big stud while on vacation, I could wear this device so I could stay in the room without our guest getting the wrong idea as to my sexuality.

"Beside," she said, "You look cute with your little cock bound up in the pink cage."

I could no longer deny her the opportunity of having a big cock. She had experienced this before. She had convinced me that our marriage was strong on the inside. I was reluctantly turned on by thinking of a big cock invading her perfect pussy and mouth. I was not sure that if I objected, she might seek this without my consent. Therefore the decision was not really mine. The decision to go along with it was mine and I put aside my fears and relied on the honesty in our relationship to quell my doubts.

When we finally arrived at the resort, I was surprised. The guests were casual and confident. The staff was most helpful and simply the cream of the crop in the looks department. Both the men and women on staff had a very quick and active nature. However, they would linger with any guest who wished to engage them in conversation. The pools and beaches were all clothing optional. We noticed that most people paid little attention to the attire or lack of attire. We could not help but notice. Our initial valet who helped us with our luggage noticed that we were probably first timers and said, "You will get used to the other guests in a few days. You all don't need to do anything you are not comfortable with."

After getting all our belongings organized, we dressed for the beach. She was wearing an obscenely small bikini. She had obviously shopped for this adventure. She took a towel and tote bag and said, "Let's go soak up some sun, Pasty." She had a beautiful complexion anyway, but she had visited the tanning booth for several weeks before. I would not think of lying in a tanning booth.

When we got beachside, we dropped our stuff beside two beach chairs and Traci made for the surf. I looked very out of place with my baggy trunks and pale complexion. I was very quick at applying plenty of sunscreen. Traci had jogged down to the beach and was wading in the surf. She motioned for me to join her. I walked uncertainly toward her. She suggested that we go for a stroll down the shoreline before we jumped into the water. As we walked along, we saw plenty of beautiful and handsome people. About half were nude. Most of the rest were dressed like Traci. A few of the older men and some out of shape guys wore baggy suits.

As we walked along, she kicked at the water and started a running commentary on the exceptional looks and conditioning of some of the most gorgeous specimens.

"Wow, Terry, look at that beautiful ass on the blonde."

"Oh my god, that brunette has the biggest tits on such a lean body."

"Do you wish my breasts were that big?"

"Terry, look, that guys cock is soft and bigger than yours is hard."

I could have done without the penis references, but she was just as complimentary about the good looking women as she was the men. I figured I could not complain if the was also pointing out hot women. My little cock was slowly rising to attention and I was thankful that she had packed the chastity device instead of making me wear it full time. When we did go into the water, her tiny bikini turned transparent. She might as well have been naked. She was also attracting plenty of attention. While I am certainly not ugly, I am no comparison to my lovely wife. I had long ago learned to take pride when people looked at us with the question of how I had such a doll with me. I even fantasized that hopefully some of the guys would assume that I had a big cock.

We both plunged into the surf and played with each other. We hugged and kissed often. In general we were really starting to enjoy our time away. Back at the room, we showered and got ready to go to dinner. The dining room was filled with many of the lovely people we had seen at the beach. I wore shorts and a tropical loose fit top. Traci wore a thin sundress with flat sandals. She did not wear a bra and her nipples and areolas were on public display. My little cock was mostly hard all through dinner.

After dinner, we made our way to one of the nightclubs in the resort. We wondered why there were two instead of one big one. This club was recommended by our waiter at dinner when we told him we had just arrived. The music was loud and the place was hopping when we got there. We got a table and ordered drinks. Traci wanted to dance so we headed out and joined the crowd. Now, I am not a bad dancer, I just don't enjoy it that much. I danced with her for five or six numbers straight and was ready to go enjoy my drink. She called me a "fuddy-duddy" on the way back to the table.

Just so happens that the table next to us heard her comment and a really good looking young guy came over. He said, "I don't want to be presumptuous, but if the lady would honor me, I love to dance."

Traci looked at me for approval. I was on the spot, but it was vacation, so I told them to go for it. They danced several numbers and he returned her to our table and thanked both of us for our hospitality. We invited him to join us for a drink and he accepted. It turned out that he was there with his brother, sister-in-law and another guy friend of theirs. He said there were more couples than single women and he again thanked Traci for dancing with him. This seemed like the perfect opportunity for us to start a discussion if he, Clay, might have the equipment for Traci's fantasy. We talked about it after we got back to the room.

Traci suggested that we might as well get ready for this eventuality just in case. She ran the bathtub half full of cold water and got me to sit in it for ten minutes. I was not sure why this was happening, but she was naked also. When I got out, my little cock could barely be seen. My balls were up in my body and I was shivering. My cock could not have been over an inch and a half at this point. She unpacked the chastity device and tried to put it on me. She had trouble getting my testicles back into my scrotum and had to massage me some so she could get the ring under my sack. She then clamped everything together and locked me in with the tiny padlock. She put the key on the table and I forgot about it.

She got out her harness and the large strapon and fucked me in the ass. I did not cum. When she was done she pulled off the harness and lay back on the bed.

"Honey, suck me off while I tell you about what I want Clay to do to me if his cock is big enough."

I eagerly gave her the best oral sex I could. My cock was dying to get hard, but the chastity device would not allow that. As the blood filled my cock, it was restricted by the cage. I licked and sucked Traci's pussy and ass. I tried to fuck her with my tongue. She moaned and then had an orgasm.

The next morning after a late breakfast, Traci told me to go back to the room and clean up all my hair whiskers. She was going by the beach shop and see if they had anything she wanted. I applied my depilatory cream and showered all my hair off. I was hairless and wearing my little pink CB6000S. When she got back she was carrying a sack. I asked her what was in it. She told me that I looked so out of place in my baggy trunks that she got me a new swimsuit. When she took it out of the bag, I almost fainted it was a white thong that was very thin.

"I am not wearing that."

"OK, I'll go down to the beach by myself then."

"I want to wear my regular suit."

"Then go chase chicks by yourself."

"No, I want to be with you."

"Then stop whining and put on you suit. Don't be nerdy on vacation, Terry. We are here to have a good time and a little more, hopefully."