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The night was magical, experiencing my wildest fantasies “cum” true and with a person I care for and trust. I was very impressed by his plan but even more so by what it took to bring it together. The time, and someone’s effort to assemble everything and I really mean EVERY THING needed for my transformation and way way more… Now I was totally convinced that Tom was sincere. Confident in Tom’s commitment Billy relinquished absolute control to Billie without any safeguards. Now that Billie could be herself, uninhibited and unfiltered for the first time ever. Billy had never given her the reins before without oversight, he had always maintained the ability to override instantly any thoughts or desires she might have. Billie was off the chain.
Sometimes, like then, when on some good dro I think out loud. Talking to myself barely above whisper I said “he has to really have it bad for Billie” the idea of Tom being pussy whipped made me giggle and I couldn’t stop. Tom rolled onto his side and slowly looked me over from head to toe. The way he looked at me, was like no one had ever looked at me before. Feeling Tom’s desire turned me on, but still I kept giggling that was until my eyes caught sight of the bulge in his speedo swimsuit. Tom seemed a little confused/concerned the more I giggled the redder his face became. It was fire engine red when he ask “what are you laughing at I certainly hope not this” then lowered his speedo ( it really wasn’t covering much LOL ) and set it free. Trying to sound apologetic my girl voice really came out “no Tom no way, there is nothing funny about that thing” and slid between his legs. I rested my head on his inner thigh so that my lips nearly touched the thick shaft of his still growing cock. I began breathing deep and slow bathing his cock with hot moist air each time I exhaled. That along with brushing my lips lightly across the head and it quickly grew to full size. Tom’s cock was sooooo hard the veins looked like they were going to burst. I stared directly into his eyes and began licking, first behind his balls then slowly proceeded upward to the swollen, almost purple head… Tom asks again “what’s so funny Billie”? I rolled my eyes and licked a big drop of precum off his cock before answering in the most sultry voice I could muster “Tom has it bad for Billie, this took a lot of planning and you did not miss a detail. I am almost as impressed with the beautiful plan you put together as I am your cock”. Needing to weaken my inhibitions before continuing I formed up four big rails, did my two then passed Tommy the straw. While he did his two I went back to the conversation completely uninhibited now. Confessing that when we were in junior high I got a good look at it while he was showering and it was way thicker and longer than mine. I know my face turned red when I told him how embarrassed I felt about mine being small, at first, until feelings of arousal took over… Half laughing I said “yes I masturbated lot while picturing it in my head, I mean in my mouth”. I got a deep breath it into my mouth until I felt his balls touching my chin several times, each time receiving a moan of pleasure from Tom. I continued to caress his cock occasionally pausing to pose questions, “was the visit to Jim’s house a setup, just a act to get me alone for a week, did Jim know what you had planned, was he in on it?” My voice raising in octaves with each question. Tom moved me up until we were eye to eye, kissed me began to answer, he looked nervous and voice sounded a little shaky, kinda unsure when he started “Billie you have been in my head for over 4 yrs and I won’t lie I have jacked off to ‘the girl in the window’ almost every night… Even having with women I always imagined it was you, well her. I truly see you as a female physically, mentally and find you beautiful and extremely y”.
To give me the whole picture Tom began with how he met Jim. They were introduced at a business meeting in Bogota Colombia and over the next year they became good friends. One evening after a business dinner they sat having a nightcap on a balcony watching guest leave, some alone, some with with a partner. Jim brought up the subject of love and ask Tom if he had ever been in love. Tom confided in Jim that he did care for, maybe even love someone but had been afraid of rejection or worse alienating a friend so never had taken a chance. Jim told Tom that’s sad my friend letting fear rob you of an opportunity for happiness and he made it his personal mission to assist Tom in overcoming the fear and taking a chance on love. “Well Billie the answer is yes, yes and yes” Tom said smiling that smile. He proceeded to lay the whole scheme out for me. Tom told me Jim had offered the sailboat, saying it would be private and romantic and that he came up with the delivering it to Santa Marta . “So the wedding was a lie” I snapped trying to look mad. Tom quickly responded “well not completely, Jim is seeing someone that lives there, they will be joining us on the boat to tour the Caribbean islands for a few weeks”. Nervous about how Jim would react Tom had waited until it was time to leave for the marina before finally told Jim how the girl he was taking was a guy he had known since elementary school. “What the fuck did he say” I ask. Tom laughed and said “it didn’t freak him out….. Much…”. He stopped briefly to take a drink of wine so I took the opportunity to speak “Tommy… Tom… Baby…. Dear shit what would you like for Billie to call you?”. While waiting for him to answer I fixed 4 lines, two tequila shots and loaded the bong. Finally he spoke “I haven’t given it much thought, I am the same person whether I am with you or Bill. How about you call me Tom and Bill calls me Tommy? It’s an easy way to tell who I am speaking to.” He tried to resume the but I handing him a shot, did my lines and pass the straw. I took a long draw on the bong and handed it to him and said “I am ready now so tell me how that conversation went”. Tom continued saying of course Jim was surprised, a little pissed off but really more hurt that Tom hadn’t felt comfortable sharing it him. After Tom apologize for assuming it would change Jim’s opinion of him and he should have known better Jim went from surprised to curious. Tom evaded his barrage of questions by telling Jim he was late to meet me at the boat and promising to fill Jim in when we all met Santa Marta. Tom asks me “can we be done for the explanations for now I really just want to relax with my girl. I about an hour we’re going to be pulling into a cove to anchor and spend a day or two sunning, swimming and ing”. “That sounds perfect” I replied then snuggled up with Tom for a nap ( yeah sure a nap lol ).
