Unexpected Adventure

I awoke to the sound of the toilet and water running in the head before seeing Adrian softly walk back to bed. "Good morning, Nicki," she said, "sleep well?"

"Wonderfully," I replied as I rolled onto my back, staring at her in the morning light. "Have you been up long?"

"Just a little while. I tried to be quiet since you looked so peaceful and I didn't want to disturb you," she responded while getting under the covers. "Go wash up and make yourself presentable before you come back here," she commanded. "You have obligations to meet so don't dawdle."

I laughed but did as instructed just to be safe.

When I returned to bed Adrian was sitting up, leaning against the headboard with the sheet only to her waist to show off her lovely breasts, flipping through a yachting magazine. "I could get used to this lifestyle you know," she said, "I just need some staff to tend to my 'needs'. Do you think that you could manage that, Nicki?"

"I would be willing to try as long as you are clear about what you want," I said with a laugh. "You just picked me up and seduced me last night so, aside from knowing your name, I have no idea what your 'needs' might entail or if I would even be inclined to meet them. You might be a vampire for all I know."

"Hmm, you're smarter than you look," she replied with a grin. "Lay on your stomach with your arms above your head," Adrian commanded while pulling the sheets down to allow me to assume the position she wanted before lying on top of me. Once satisfied, she adjusted her erection at the entrance to my anus and then gripped my wrists in her hands. "You promised to provide me with breakfast when you convinced me to remain as your captive on this vessel last night but so far I have not received a morsel of food and my body is digesting my organs." She pushed the head of her stiff cock a little way into my ass before stopping. "You also 'viciously' sodomized me in the early hours of the morning before allowing me to rest briefly," she laughingly continued while pushing deeper inside me.

"You forget that you climbed on top of me and after having your way with me slept all night undisturbed in my bed," I countered while stifling a laugh.

"Silence!" she hissed as she pushed her cock balls deep into my ass. "Now you will suffer the consequences for your actions and your insolence." Adrian began a gentle in-and-out motion while kissing my ear and neck and softly whispering how she was going to enjoy making me her bitch.

Within minutes she was hitting the perfect spot to bring me to the edge and her words aroused me even more. I was drifting away on clouds of emotions when suddenly I was engulfed in a marvelous orgasm with semen pulsing from my penis. Adrian cried out while pushing deep and squeezing hard on my wrists as she came, gripped by spasms that shook her body until she became limp upon my back.

After a few minutes of rest, Adrian rolled off and lay next to me. "And let that be a lesson to you, slut. Now, where is my breakfast?" she said with a laugh.

We rolled around on the bed kissing and enjoying the light-hearted moments that occur in the early stages of a pleasant newfound relationship before we got up and went to the galley to prepare coffee and I assembled the makings of breakfast. Our conversation was easy and light and it appeared that we were able to maintain a good mood from the prior evening's dinner and afterward. It was enjoyable being with her and simply fun.

After I cleaned up the dishes and Adrian made fresh coffee for us, we went to the upper deck to take in the late morning sun. We had had a great evening, a marvelous night together, and now an enjoyable morning; I wondered where it was going to lead as it seemed too good to last. Adrian must have had similar feelings as it was she who first mentioned the elephant in the room. "Nicki, this has been great, and I had a wonderful time with you," she said. "It is so easy to relax around you and simply be myself. We clearly have a similar sense of humor and seem to like so many of the same things but I need some fresh clothes, so I have to leave even though I don't want to. I don't want to parrot the usual 'morning after' dialogue since I don't think that would be fair to either of us, but much of the usual stuff is fitting here so I will anyway.

"Nicki, I had fun, real fun with you and I would like to see you again if you are inclined to see me. I am not going to pressure you so if you do not feel the same way simply tell me and I will understand. I may hate you and stick pins in a handmade doll before I throw it into a fire but those are details that we do not have to discuss right now," she said with a slight self-conscious grin.

I laughed at the obvious joke that disguised her emotions and reached for her hand before replying. "Adrian, you are truly unique and I have enjoyed our time together, short as it has been. I feel a comfortable connection with you and I do not want to lose the opportunity to see where it may go if we give it a try. I definitely want to see you again and since you have much more work to do making me your bitch, let's make some plans while we enjoy our time on the Cape. If you want to get some clothes and come back to the boat, that's great, or I can meet you where you are staying later today. The choice is yours but I would be happy either way."

Adrain flashed a big smile, leaned over, and kissed me hard on the lips. "I want you to fuck me until I scream," she said. "Oh, shit, did I say that out loud?"

"Say what?" I replied with a smile.

"Whew, my reputation is safe," she said with a laugh. "Okay, then if you don't mind, I will freshen up and go get some clothes and meet you back here. My place is not as comfortable as this and with my friends due to show up any day it is not how I want to spend our first few days together. There are some nice clubs around here so I think we could have a nice time being around the marina."

"Sounds great and I will be looking forward to it," I replied. "I have the boat for a couple of weeks and I want to hear you scream."

True to our plan, Adrian left and returned late in the afternoon with her overnight bag and all the essentials that she needed for a few days. She settled in nicely, was neat and helpful with the daily tasks, and she had the easy-going demeanor befitting someone sharing close quarters. Within the first day, she knew our neighbors by name and chatted easily with people on the walkway to the other boats. All of this made me wonder why she was not taken by some other guy by now but over dinner the first night she confessed the same question to me. I told her that perhaps I was too picky in my romantic interests and never found someone compatible enough. Then, when I eased off in how I felt, I wound up getting disappointed and hurt. She admitted to being cut from the same cloth and did not want to be hurt anymore. I asked her why she felt differently this time and after taking a minute to compose her thoughts she said, "You appeared genuine when you said that you were concerned about how I would get home after dinner last night and going to the boat the first night you asked me to stay to make sure I would be okay. It was a simple selfless comment but it said a lot about the type of person you are. I felt that you were worth the risk of possible pain."

"I hope I don't disappoint you," I replied quietly.

The second night on the boat we were treated to amazing music and partying coming from the restaurant by the pool so we decided to head over for a drink and a late dinner. It was a relaxed and lively affair with people in beach attire dancing barefoot to Latin salsa music mixed with hip-hop and we happily joined in. It was a great time with a friendly crowd and plenty of free-flowing alcohol to fuel the evening. At one point I had to excuse myself to take a call from my brother who was concerned that I was getting along okay on my own but was relieved when I said that I was having a good time and that I met someone to share the experience. He confided in me that he considered coming back early from his holiday if I was feeling isolated but could now relax when I said that it was shaping up to be the best summer trip in many years. We had a few laughs and he asked that I take care of the boat since it was his baby. Now I knew why he really called and kidded him about his screwed-up priorities which elicited a hearty "fuck you" and a laugh as he hung up.

As I walked back to our table I noticed Adrian salsa dancing with another female, both laughing and smiling. When she saw me she put her hands on her hips and gave me a sexy 'fuck-me' look and gyrated her butt in the direction of the other woman who then took Adrian's hips in her hands and pulled her close as she danced. This show took my breath away and Adrian knew it, giving me a big grin before turning to face the woman and kissing her on the cheek, and then dancing over to me.

"God, you're driving me crazy," I said.

"Oh, were you watching?" she replied, and we both burst out laughing.

At this point, a waiter came over and handed us two double shots of tequila saying that they were the compliments of the female Adrian was dancing with, and as we looked over she and a male friend raised their glasses in a toast and finished the liquid in one swig. We matched their action and I asked the waiter to send a matching drink to the woman and her companion as a quid pro quo. After catching our breath for a few minutes, Adrian suggested getting some food before the kitchen closed which we did as we listened to the music and watched the dancers.

After dinner, we headed back to the boat arm-in-arm enjoying the after-effects of a nice dinner, fun music, and good tequila. "That was fun," said Adrian as we walked.

"Yes, I really enjoyed it," I said, "I never would have guessed that you were such a great dancer, you are full of surprises."

"It is a passion of mine," she responded with a smile. "People tend to lose their inhibitions as they feel the music and you can get close to other people without the intimacy and complications of sex." I returned her smile and we walked the remaining short distance in silence.

As we got comfortable in bed Adrian asked about the call from my brother, jokingly asking if he was throwing us off the boat. When I said no, that in fact he was concerned that I was okay but more importantly that the boat was okay. She laughed, adding that it was nice he cared about me. I had to agree and said that it was nice she asked. "Of course my dear, you should know that I care about you, too," she said with a serious note before adding, "Now, be a good slut and pleasure me."

"Yes, mistress," I said and slowly leaned over to place some soft kisses on her neck, working my way down across her lovely breasts, her stomach, and abdomen until I took her now erect penis into my mouth eliciting moans of delight as she wriggled in anticipation of what was to come.

After a wonderful bout of mutual gratification, I lay in bed with my arm around Adrian as she drifted off to sleep, feeling a sense of peace I hadn't felt before, wondering where she came from and how she found me, the person who needed her so badly. "You enjoyed watching me tonight, didn't you?" she asked softly with her eyes still closed.

"Yes, very much. You are very erotic, and I found it exciting seeing you with another woman," I said.

"Good, I was hoping that you would," she replied as she drifted off. With those words, I rolled onto my side and held her as we spooned and allowed sleep to cloud my eyes.

Waking with the first rays of sunlight changing the darkness to the soft glow of morning, I felt Adrian move as she got up and went to the head. When she returned to bed I got up and did the same before resuming our position. I felt the softness of her skin against my stomach and legs as she pressed herself against me and this immediately awakened my subconscious desires, causing an erection to materialize which I tried to subtly adjust without calling attention to myself. Ever so gently, I moved to place my stiffening penis in the crack of her buttocks and between her legs but this movement excited me further. Before long I could not conceal my longing and almost without guidance from me, my erection found its way to the entrance of her anus where it halted momentarily waiting for the slightest pressure to advance its journey.

As we lay together in this state of limbo I became very aroused and wanted her more than ever. I increased my grip on her slightly and felt her body respond to the pressure by relaxing her sphincter muscles permitting my penis to slip into her anus and gently slide farther into her body. Adrian did not react to this penetration but lay there silently without moving, eyes closed as if asleep. Once I was fully inside her I remained motionless while feeling her breathing and the contraction of her muscles gently massaging my erect penis. I focused my attention on my loins and Adrian's rhythmic breathing and stillness as I penetrated the recesses of her body without resistance.

Several minutes of this tantric bliss brought me to the edge of orgasm and as I tried to gently withdraw myself, I erupted into orgasmic spasms which caused me to pull her to me more tightly than I believed possible and forced me deeper inside her. I buried my face in her neck and moaned in ecstasy as she gripped my arms with all her might and whimpered in delight. Together we shook in reaction to the orgasms we experienced before finally resting limply in our bed that was now damp from sweat.

"I spent a couple of nights on this vessel out of necessity and so far I have been viciously sodomized twice and forced to perform fellatio," she said. "You, sir, are a brute and will have to suffer the consequences for your actions. You shall rue the day that you violated me orally and anally."

"I seem to remember one night where my face was in the pillows while you held my wrists and forced yourself on me as well so that makes us even," I replied.

"I was defending myself when you tried to take advantage of my helplessness," came the response as she held the pillow to her breast indignantly. "I feel the need for coffee so be quick about it or I will scream."

"You're quite mad, you know," I said with a laugh.

"Quite!" she replied laughing loudly as well.

As we sipped coffee and rocked gently to the waves created by passing boats, Adrian said that she had a great idea to help pass the time after we return from the beach until it was time for dinner. I was intrigued so I asked what mischief she was dreaming up but certainly was not prepared for what she proposed. "Well, I want you to keep an open mind and not dismiss the suggestion until you hear me out," she said. "It involves trust on your part but I will guarantee that it will be a different experience, something quite stimulating, and you may actually enjoy it."

"Okay, you've piqued my interest and I promise that I will not say anything until you say that you are finished with your presentation," I responded. "You have my attention so the stage is yours."

"Nicki, you are an attractive person and I have come to conclude that with a little bit of help, you could be gorgeous," she said with a mischievous tone in her voice. "You're slim like me, speak softly, and have a gentle quality about you. These are all positive attributes and coupled with the good looks presented in bikini bottoms, I would bet that you would be ravishing in full make-up with a miniskirt and spaghetti string top."

I was nearly speechless and wanted to protest against the idea but true to my word, I held my tongue and let her continue after a brief pause. "Nicki, I don't know if you have ever worn more than bikini bottoms in public but I know that you would be beautiful," she said softly. "On top of that, you said how exciting it was to see me dance with another female so imagine how exciting it would be to stroll together, holding hands or arm in arm, maybe slow-dancing, while both presenting as female. The people who saw us together would think that we were a couple of lesbians out for the evening while we knew that we were secretly trying to contain erections in our panties. Oh, God, I'm getting aroused already.

"I have everything we would need with me except a wig but some women have taken to slicking their hair back with some gel or wearing a straw fedora, so you could pull this off without one. Plus, imagine how it would feel to make love to me as a woman. I will wager that you will be screaming with pleasure as you cum and I guarantee that I will."

Adrian took a sip of coffee and waited. I watched her expression and looked into her eyes, the excitement and anticipation clearly apparent, and wondered how serious she was about her suggestion. I admit that I have worn women's clothing in private and I feel that I look quite presentable, but it is another thing to go out in public, mixing with other people in a skimpy outfit. Still, the thought of walking around with Adrian as a female excited me and I wanted to see what it felt like. Adrian was lovely, had beautiful breasts and a gorgeous body, and had been presenting as a female for a very long time so it is natural for her, but will I be so self-conscious that I make a fool of myself? It is a tough choice but an exciting one as well.

"Okay Nicki, you're very quiet so what do you think? Do you want to try something different, with the reward being the greatest lesbian sex you could ever imagine at the end of the evening or do you want to settle for the ho-hum life of fast food and falling asleep in front of the TV?" she questioned. "The choice is yours."

"Adrian, I must hand it to you, you have a way of getting my attention. I thought about you dancing with the other girl and pictured us doing the same thing so I had a hard time moving on from there. Are you confident that I will not embarrass myself if I am out in public in a miniskirt?" I said.

"I don't know if you will embarrass yourself or not, but it will not be because you don't look like a ravishing woman," she replied. "I also don't want to embarrass myself by being seen with some less-than-beautiful chick on my arm. I do have a reputation after the other night, you know."

"Well then," I said, "since we have our work cut out for us this afternoon, let's go to the beach to relax first."

"Good idea" she responded, "I need some salt air to get my creative juices flowing."

A few hours of swimming and lying around together proved to be exactly what we needed. We talked about the evening ahead and I could see that Adrian was looking forward to it as much as I. Adrian told me about the clothes that she had in mind for me and as she did so I formed mental images of how I would look and hoped that I could live up to her expectations. The worst case in my mind would be that I fail to pull it off and we have a good laugh at the silliness of it all so no harm, no foul.

Walking back to the boat I asked, "When did you first go out in public as a female and what prompted you to do it?"

Adrian was quiet for a minute and then replied, "I had left home for college and had a small apartment in town not far from school. It was the first time that I could indulge my inner desires without offering explanations to anyone. I had come out as gay years before and that was not so much of a problem but I knew inside that it was a step on a journey that still had a way to go. After classes and on weekends, I would wear sexy things at home but I hesitated to go outside for fear of embarrassment although I felt that this was the real me. One night when I had grown tired of my double life, I picked out a nice skirt and sweater, pantyhose, and heels, did my makeup, put on an attractive wig, and following a shot of tequila for liquid courage, walked to the local restaurant bar. I was alone and very nervous but I made up my mind and there was no turning back. As I walked the sidewalks, I wished that I had someone to walk with me and have my back just in case my resolve weakened and I tried to run home again. Before long I had reached my destination and I knew that I could not go back.