Captain John's Playmate

Alessia Travestita's Adventures - Episode 1 - Captain John's Playmate.

It was forecast to be a gloriously warm and sunny day, clear blue skies with a gentle warm breeze from the South. So I decided to leave the town behind and head out into the countryside for the day, get some fresh air, toning exercise and of course, top up my tan.

We have a lovely stretch of the River Weaver nearby which winds for several miles through the heart of the quiet Cheshire countryside, popular with both pleasure-boaters and walkers. There is a good footpath alongside the river but I decided to err on the side of caution and forgo the high-heels and I opted for a pair of comfortable white trainers, my skimpiest black bum-hugging tight velvet shorts and a low-cut white vest-top with a black lacy push-up bra underneath. I brushed my long blonde hair, topped it off with a pair of sunglasses, grabbed my bag and headed out into the warming day, feeling toned, tanned and sexy.

After an hour or so walking I was getting thirsty in the hot sun, so when I came upon a traditional English riverside pub I stopped off and took a seat at a vacant outside table near the riverbank, close to a long line of pleasure boats tied up at mooring points. I stretched out my long, slim legs in the sun and threw my head back to feel the sun on my face. In a couple of minutes I was disturbed from my daydream by a young petite waitress so I ordered a medium glass of white wine.

Before she returned my attention was taken by a strikingly handsome gentleman emerging from the doorway of the hostelry. Possibly around sixty years of age but clearly in good shape, apart perhaps from a bit of weight around his middle - he had the look of someone who enjoyed the finer things in life, and could afford to do so. Tall, around 6ft 2in, and broad shouldered, he sported an all year round 'sailors' tan and had a distinguished, confident air - someone who knows what he wants, and is accustomed to getting it.

He paused just outside the doorway and quickly looked around as if scanning the tables. When his gaze came over in my direction he seems to pause slightly but then continued to scan round as if not to draw attention to it. Clutching a large balloon glass of some spirit over ice, he made a beeline for my table and politely asked if he could share my table as the rest were filling up now lunch was imminent. Of course I was more than willing. He introduced himself as John, and I returned with Alessia, just as the petite waitress returned with my glass of wine, for which my new acquaintance insisted on paying. The waitress looked at me and winked mischievously, as if sharing some sisterly secret. My interest was piqued.

We chatted together pleasantly for a while about this and that, and he told me he was on a short trip out in his yacht, which had just been refurbished and serviced, so he was giving it a 'sea' trial on the river. When I enquired which one was his he pointed out a glorious looking yacht, named 'Great Escape' - all dark wood, brass and yacht varnish. I guess it was from the 1950s or 60s but in showroom condition and as classy as you can imagine, with a flag fluttering on the stern and a large seating area. To be honest, I was not all that surprised when he asked if I'd care to join him for the next leg and promised to drop me back off on his way back down in two or three hours. Naturally I jumped at the offer.

Finishing our drinks, rather more hastily than seemed decent, we stood and he led me over to the yacht. He gentlemanly took my hand and helped me over the transom. Looking around I could see it had a large seating area at the stern with an L-shaped settee and a couple of matching armchairs. Forward of this there were two sets of steps, one on the port side leading down steeply into the interior and another on the starboard leading up to the flybridge, where he proposed we went, as that gave the best view of the river and the country and with the awning drawn back we could continue to enjoy the sun as we wafted upriver.

I perched myself on a large lounger that was next to the wheel and control panel, while John disappeared down below, to re-appear a moment later with a large ice bucket with a bottle of champagne and two glasses. I knew then that I was in for some 'entertainment'! I heard a deep throb from down below as John started the twin diesel engines and while he allowed them to idle for a few minutes he poured us each a glass of ice cool champagne and proceeded showed me around the yacht.

It was certainly something to see, genuine Italian craftsmanship, glorious woods of various hues and grains, polished brass fittings all over, soft pile carpets, a couple of what looked like original oil paintings (I didn't want to peer to closely) and some fine Romanesque sculptures. At the fore of this large cabin was another set of controls, the same as on the flybridge, for sailing in more comfort or in the rain, behind a row of three cream leather 'captains' chairs. The focus of this bridge area was a huge ship's wheel in the traditional style, a large eight-spoked wooden affair with a central brass boss and the eight spokes protruding outside the wheel for easy handling.

'Right, engines should be warm now' said John. 'Shall we go up?' and he led me back up the stairs to the flybridge before he returned and cast off the fore and aft mooring ropes. Returning to the bridge, he throttled up the engines and expertly swung the boat out into mid-stream and headed upriver. I kicked off my shoes, settled back down on the sun lounger and John expertly angled the back for me so I could watch the beautiful countryside slide past while catching the sun on my legs and arms. We chatted pleasantly as we glided along and I found John's company stimulating and relaxing in equal measure. There was a keen flirtatiousness about him but it never felt tacky, always having a sophisticated, gentlemanly air.

With the warmth of the sun on my skin and the effect of the chilled champagne, I could feel myself relaxing and enjoying that slight numbing of the senses you get when drinking on a hot day. Attentively, John reached over and refilled my glass with a twinkle in his eye. 'If I'd known I would end up here I'd have brought my bikini' I ventured.

'Oh, don't let me stop you' replied John, 'No-one can see you up here on the bridge, feel free!' I needed no further encouragement and stood up, slightly too quickly, and laughed, realising that the champagne had gone to my head rather. Sticking my thumbs into the top of my shorts, I peeled them down and off, pulled my vest top over my head and in a second stood in front of John wearing just my black lace panties, matching bra and a big, cheeky grin. 'Wow' was all he could say for a minute or two until he managed to come back down to earth. 'You really are stunning Alessia' he reacted and clearly could not take his eye from the bulge in my panties. 'You really have all the equipment in place, don't you?' he continued as I lay down full stretch on the lounger again.

Taking one hand off the wheel he flipped open a small locker and drew out a bottle of sun cream and passed it my way. 'Here, you may want to try some of this, the sun's getting quite fierce now.' I took the bottle, flipped the lid and poured a generous handful of the sweet coconut smelling cream out and gently smoothed it onto my legs, arms, and tummy. I lay back and massaged the soft cream in slowly and when I reached my panties I continued, easing my fingers inside and continuing to rub the remaining cream onto my huge cock. Warming to the situation, never a shrinking violet, I was now effectively masturbating in front of John, enjoying teasing him and loving him watching me.

'I might need some help with my back in a while if you wouldn't mind?' I ventured.

'Of course, just let me know' he responded with a huge smile, his breath coming quicker than before.

Closing my eyes I let my mind drift, simply enjoying the feeling of the sun and the gentle breeze on my lithe, tanned body. After perhaps half an hour more, I heard the note of the engines change to a more muted tone and opened my eyes. 'This is where we turn to head back Alessia' John explained. 'We can pull in here first though for a bite to eat if you'd like? This is a lovely quiet spot for a break and I've some food in the fridge if you'd care for something?'

'That would be nice John, and while we are here you can do my back for me too.'

'You bet!' John laughed and skilfully guided the boat up against the bank, jumped down the steps and threw a rope onto the bank. Jumping after it he secured it around a large tree trunk as this was not an official mooring site, just a quiet, isolated stretch of the river.

Returning on board, his mind was obviously not on food, as he sprang up the steps and said 'Right Alessia, time for your back!' and took up the bottle from the floor where I'd left it. I obligingly turned over onto my front, spread my legs just slightly and reaching around, unhooked my bra allowing it to fall free. John knelt down beside me and I could hear his breathing as he gently squeezed the bottle over my back, starting at my shoulder, working down my back, the exposed parts of my bum and my upper thighs. He then placed the bottle back down and moved his hands back to my shoulders and gently massaged the cream with an experienced, firm motion.

Moving down, he continued to work on my lower back, using his hands expertly, and I felt a thrill run through me as he reached my bum and carefully started working on the skin around my panties. Sure enough, his drive soon got the better of him and he slid his hands under the top of my panties and drew them down to my knees leaving my bum exposed, which he then started working on eagerly, rubbing and kneading the cream into my crevice.

After a minute he put his hands gently under my hips and motioned me to raise my bum slightly to expose my anus more. He then gently squeezed some cream directly on my hole and very gently pushed first one finger, and then two into my soft wet ass and started to gently work them in and out gradually going deeper and deeper as I clench my muscles to grip his fingers, enjoying the sensation of being dominated. He quickly realised that I could take more and withdrawing his fingers gently rubbed the cream over his whole hand and also poured a generous amount on my now gaping hole. Pushing the same two fingers back in John pushed deeper this time and then slid in a third and then a fourth finger until he had his entire fist inside me when he paused to allow me to enjoy the amazing sensation of that fist, filling me up inside. I squeezed my anal muscles hard on his fist and could feel it being pulled in further and further by my actions until I relaxed and we both paused for a minute to enjoy the deep, intense sensations.

John then gradually started an increasing in and out pumping motion, almost pulling out of my ass but then pushing back in until I could feel his fist hard up against my prostate, at which point I could not but help give a stifled moan and cum hard, squeezing my sphincter hard around his wrist, anchoring his fist in place until I had come hard and fully and only then releasing my grip. John was clearly surprised and pleased at my expertise, but he was in no mood to finish, he wanted his fun too.

'Quick, downstairs Alessia!' John panted, almost shouting in his excitement. Needing no further encouragement I jumped up, now stark naked and we both hurried down the steps into the lower cabin. John grabbed my hand, kicked the door shut and led me over to the ships wheel and pushed me up against it, face first, legs spread apart. 'Stay there!' he commanded and opening a cupboard just below, he took out a couple of lengths of red rope. Almost before I realised what he was doing he had lashed one end of a rope to one of the wheel handles, pulled my arms down across my back and then run the rope tight across my back, trapping my arms, and then looped the rope end around the opposite handle and pulled it tight. He then took the second rope, looped it around the lower half of the wheel, round the back of my knees and back around the wheel. I was totally trapped now, lashed hard up against the wheel, unable to move.

Turning my head as far as possible, I could just see out of the corner of my eye John undoing his belt and dropping his pants to the floor he kicked them away. My eyes popped when I saw the size of his manhood - it must have been fully eight inches long and with an impressive girth to match. And straight and hard as a ramrod with a huge bulbous glans. Without a further word he leaned into me, pushing me hard up against the wheel and I felt his powerful hands grip hard around my buttocks. I felt the hot tip of his huge cock pushing up against me and in an instant he had entered me, my ass still wet and gaping from the previous fisting.

Moving slowly at first and then harder and faster, deeper and deeper he fucked me like there was no tomorrow. He seemed to last forever, helped by the lubrication of the sunscreen and the previous fisting which had temporarily loosened my hole, but gradually I could feel him starting to tense up. After what seemed like an age of harder and harder fucking with his battering ram of a cock, with a cry he came hard and flooded my inside with jets of hot creamy cum. He pushed in hard as he came so I could really feel the pulsing of his mammoth tool as he shot load after load deep inside me. Trapped hard against the wheel the experience was so intense and extreme I suddenly convulsed with my own huge orgasm, my ass squeezing hard on his hot member and myself shooting a flood of my hot love juice onto the polished floor below.

He stayed pushed deep inside me as his body relaxed and he deftly slipped the ropes off the wheel and let them fall to the floor. He moved back slightly to release me from the wheel and motioned me to turn round and then putting his large, powerful hands on my shoulders gently pushed down to indicate I should kneel. I knew exactly what he wanted and was eager to comply. I dropped to my knees in front of him and took his hot wet cock in my mouth, eagerly sucking and massaging the last drops of cum into my mouth until I had totally drained him. He held his softening cock in my mouth and I swallowed it down deep into my throat until his shaven ball sack was forced against my chin. He forced me to hold it deep down in my throat until the last of the pulsing had died away and he was truly spent. Only then did he release his hand from the back of my head and allow me to release his manhood with a gasp.

Breathing heavily and with trembling legs we both moved up the stairs and back into the sunshine of the bridge, where John, ever the gentleman host, poured me another glass of champagne. After a rest to recover ourselves, he fired up the engines and we continued our journey back to my starting point. I remained totally naked for the rest of the trip, letting John enjoy the view inside the boat as I enjoyed the view outside the boat. Needless to say, we will be cruising together again shortly.