I'm surprised by what flows out as I write the story. Yes, it started out being a very autobiographical account, however has now crossed in to a strictly fictional space. I'm sure a few years of analysis will help me sort it all out! You've almost got to read the first parts of this story to understand what's going on, but for those with short attentions, I'd suggest starting at chapter 7 and reading from there...
The next morning I woke to the smell of bacon and eggs. Matt had ordered room service for us with all the trimmings. We sat at the window in the glorious morning light of a beautiful summer day. Everything seemed to sparkle that morning, and we laughed often while we ate our meal playfully. I began to feel quite amorous by the end of the meal and tried to be as provocative as I could be, hoping that Matt would take the bait. He didn’t take the bait though he was quite aware of my intentions.
“There will be plenty of time for that later. Now I need you to shower and get ready for today.” He spanked my ass playfully.
“And when you finish put this on - we’ll be swimming today for sure.” He handed me a small, tissue-paper wrapped bundle and nodded his head towards the bathroom.
I showered and took care of things quickly, deciding to go without makeup given the heat and the likelihood of swimming. I opened up the package that Matt had given me and found three exceedingly small triangles of a red mesh material that were tied together with matching string. It was a bikini so small that I didn’t really think it would cover anything - I ended up being mostly right about that. It took a few moments to figure how to tie it on; when I looked at myself in the mirror I was quite stunned to see just how racy the garment was. While my breasts weren’t big at the time the material of the bikini was so small as to leave me mostly spilling out of the no-bigger-than A-sized cups. The bottoms were thong style and I was very glad that I’d been waxed quite thoroughly down there or I’d have needed to shave.
I paused for a moment in the mirror. I’d never been vain about my looks, though I did consider myself to be attractive. I certainly never went out of my way to draw attention to myself. But Matt was starting to change that. It was clear from the way he was having me dress in front of others that he really liked the way I looked at wanted to show me off. I didn’t think about it too much then - my desire to please Matt was leaving me without much time to self-monitor and think about what I needed or wanted.
Matt tapped on the door and I quickly slipped some shorts and a T-shirt over the swimsuit and slipped into my flip-flops. Opening the door, I threw my arms around Matt and kissed him.
“You should be very glad I went to the waxing salon last weekend or this wouldn’t look nearly as good as it does” I whispered into his ear.
“I can’t wait to see. Now let me shower quickly and we’ll be off.”
Half an hour later we were in a cab driving down the lake shore to a marina where Matt’s buddy, Milo, an old college friend who Matt told me had “made it big with an already big trust-fund in the stock market” was waiting for us. We arrived at the marina, grabbed our bags and headed towards Milo’s slip. As we walked Matt told me that I was to simply call him Matt today, but that I was still to do as I was told without hesitation. I smiled and said “Yes Sir!” trying to fake a naval salute at him. He pretended to try and push me in to the gunky water in the marina but ended up groping me playfully.
We rounded a corner and arrived at Milo’s long sailboat that was named “Boilermaker II”. Milo was at the wheel playing with some gadget there and looked up as we approached. Milo was a very attractive man, though different than Matt. He was shorter than Matt, probably about 5’11” or so, he had thick dark hair that he wore long. He had a softer face than Matt and seemed to carry more weight on his frame so that when compared to Matt he appeared to be almost stocky. He was also more thickly muscled than Matt, with a barrel chest and thick arms and thighs that made me think he’d probably given up swimming for weights. He was very handsome in a way totally different than Matt, less masculine and hard, more pretty and innocent (boy, how wrong my impression of him would turn out to be). When he saw Matt and I he dropped what he was doing and greeted Matt as we stepped on to the boat with a big bear hug and several back slaps that seemed to make Matt wince a bit.
They exchanged greetings for a few moments, making a few inside jokes that were undoubtedly references to women and drinking binges in their past. While they were doing this I noticed that Milo would occasionally glance over at me, letting his eyes wander up and down, but never quite making eye contact.
Eventually Matt noticed this and turned to me, “And this is Amy. She’s been looking forward to meeting you. Be a good girl and say hello Amy.”
He smiled at me and stepped back. Not knowing exactly what he meant I stepped forward extending out a hand, but Milo knew exactly what he wanted and wrapped me up in the same hug that he had given Matt, it made be feel so small. He held the hug for a few moments and I felt his powerful chest pressed against mine as his hands ran down my waist to my hips, not quite making it to my ass, but certainly giving me a more friendly greeting than I’d expected. He let me go and I looked to Matt who was now smiling in a more devilish way at me.
“She’s an amazing woman Milo. I can’t even begin to describe how amazing she is.”
“No need my friend. No need. I can tell by the look in your faces. I’m sure we’ll all have fun today on the boat. So let me get Jen, she’s changing below.”
He turned towards the cabin on the boat and called out for her. I heard a rustling below and then saw Jen’s blonde hair appear in the doorway to the cabin. By the time she reached the deck where we were standing I think that both Matt and must have been standing there with our mouths open and our eyes wide. Jen was gorgeous - model gorgeous
. She was as perfect a woman as I’d ever seen in my life, from head to toe she looked perfect. Her blonde hair fell in soft curls around a face that I couldn’t help but want to look at. She had the blue eyes and a button nose above dark red, full lips that looked like they’d been made for kissing. Her face fell almost in the middle between sharply angled like a model’s and softly feminine. Her skin had a healthy tan that made her lips and hair stand out even more. Jen was wearing a perfectly fit white bikini that was much more modest than the one I had under my scruffy clothes, and despite its modesty I couldn’t help but think it was more sexy was well. She was probably about an inch or two shorter than I was, perhaps about 5’8” or so. She wasn’t skinny by any measure but she didn’t appear to have an ounce of fat on her frame either. She had much larger breasts than I did, at least a C-cup, and they complimented her frame perfectly. Her waist was hourglass-shaped and flared into gorgeously curved hips; feminine hips that gave way to the long taper of her perfectly toned legs. She was, in a word, perfect. And in an instant I felt perfectly inadequate.
She greeted us both with a warmth and elegance that flowed from her as naturally as she breathed. She gave Matt a hug and whispered something into his ear as she did so. He laughed at this, breaking the hug and holding her at arm’s length as he looked her up and down.
“You look great, is this backstroker taking good care of you?” Matt asked nodding at Milo with a wry smile.
“Well, despite his proclivity to be on his back I’d say he’s taking wonderful care of me.”
She turned to me, “And you must be Amy, I’ve heard so much about you from Matt and Milo.”
She walked up to me and gently and brushed a lock of hair from my face, “Your even more beautiful than Matt said you were.” She embraced me and somehow all the jealousy I’d felt evaporated.
“Why don’t you come down into the cabin with me and you can get changed while the boys play with the toy?” I could only manage a nod and we were off, dropping down into the darker space of the boat’s cabin.
Once there, Jen lead me the forward cabin where she said I could get changed. The boat was pretty big, she mentioned that they could sleep up to 4 couples at a time, and as she was closing the door she said, “But who sleeps as couples?” I contemplated that as I removed my shorts and t-shirt. I set them aside and checked out the room a bit. It was obviously the ‘master’ bedroom (or its boat equivalent), as there were several very revealing and risqué but artful photos of Jen on the walls, all clearly taken by a professional. I was completely taken by the images. They all made Jen look even more beautiful and more glamorous. In several of the images she was wearing lingerie, that was similar to the lingerie that I’d worn the night before, though of course I couldn’t help but think that she filled hers out far better than I had. I found myself lost in the images, in the beauty that had been captured in the simple images and the way that she looked a bit different in each image though was instant recognizable as well. I was looking at the images, imagining what it would be like to pose like she had - to feel the photographer’s eye on me, when I felt a gentle touch on my shoulder snap me out of my daydream.
“I like this one the best” I heard Jen whisper from behind me, pointing at a black and white image that had the most simple composition of any of the images, a simple photograph of her hips and ass against a white background.
“I don’t think my ass has ever really looked that good, and I’m sure it certainly won’t ever look that good again.” I heard her laugh a little at this.
“Though I bet you haven’t really thought about that, have you?” She patted me on the ass playfully.
“You must have been distracted, eh? I was wondering what was taking you so long. I could have put on that costume in the time you’ve been in here.” Jen pointed at a different image in which she was dressed in very sexy lingerie and was wearing her hair dark and her boots tall and spiky.
“I can’t believe how beautiful you are. Have you been a model for a long time?”
“No, not long” she replied. And these aren’t even my work shots. Milo took these a few years ago. I’ve only done a few jobs here and there since.”
When we returned to the deck I was surprised when I got a long whistle from Milo who was standing at the wheel, "Well that's certainly an improvement over the T-shirt and shorts wouldn't you say Jen?"
I heard Jen snicker a bit behind me, "You don't know the half of it Milo. So are you going to get us out of this marina, or do you need a real sailor at the helm?"
I'm sure I blushed a bit at her comment but doubt that if in the bright sun anybody noticed. I slipped on my Wayfarer-style sunglass, all the rage at the time, and looked forward to find Matt. He was standing on the dock, holding a line that was attached to the front of the boat and looking bored. After what had just happened to me I didn't think that we'd be bored in the least during our trip today. I turned to walk up to the bow to see what Matt was doing.
As I turned I heard Milo guffaw and whistle again. "Oh my god Matt, that girl is even better going than coming!"
Without even looking I flipped Milo the bird – he just seemed so playful and casual about things that I didn't worry that I'd only met him in the last hour or so. "What! And she's got attitude to match that ass? Hey Matt, you've got the whole package here, don't you."
"Fuck off Milo … are you going to drive this boat, or what? It's hot here" came Matt's reply as he watched me scoot up to the bow.
"What are you doing?" I asked.
"I'm getting ready to walk the bow out of the slip. I'll jump on when its clear, but somebody apparently doesn't know how to start his own boat." The last part loud enough for Milo to hear. Matt seemed quite annoyed and I didn’t understand why. I’d certainly been doing everything I could to please him.
As if to respond to all the flack he'd been getting, I heard the muted sounds of the engine start. I looked back to the wheel to see Milo still at the wheel while Jen stood behind him, arms draped over his shoulder. She was whispering something in his ear and as she did so he was looking at me. When she finished he turned to look back at her, a questioning look on his face, then back to me.
Noticing I was watching he called out, "Prepare to cast off." Then a moment later he called "cast off" and the boat started backwards out of the slip.
Matt walked along side of the boat till he was almost out of room on the dock, grabbed a metal cable on the boat and hoisted himself up the side. "Bow's clear". The boat made a turn and Milo pointed us out towards the relatively calm blue water of Lake Michigan.
We motored out for a while then Milo told Jen and I to raise the main sail. Jen showed me what to do which mostly involved pulling on ropes and enduring Milo's snide commentary about my bikini and me with Matt's occasional quips about Jen thrown in for good measure. There was a nice breeze on the lake today and as soon as Jen and I had the sail up Milo turned off the noisy engine and we started to sail north along the lakeshore. Milo then had Jen and I attach and hoist up the jib sail on the bow of the boat. It was a bit more work as it wasn't already attached to its lines and standing on the bow wasn't as easy as standing back by the mast, but we managed ourselves pretty well and soon we were sailing under full white sails at a pretty good clip.
Jen asked me if I’d like to help her get some drinks from below and we went down to the galley after asking the men what they wanted. Below Jen went about getting the refreshments ready while I mostly got in the way. After preparing a tray to bring up she handed me a glass of white wine.
“You really are a beautiful girl Amy.” She said, looking directly into my eyes.
I blushed and felt a shiver run down my arms and legs. I’d seen the same look in Matt’s eyes in the shower those many months ago.
“I… errr” I had no idea how to respond.
Jen moved in closer. “Do you like being with Matt?”
“I do. I think I love him. He is so good to me and I just feel so comfortable when I’m with him.”
“He is a wonderful man. But don’t let that limit you, ok? There are a lot of adventures waiting out there for a girl like you.”
Her eyes took me in from top to bottom. She leaned in and kissed me gently on the lips. I was surprised; though at some level I’d expected it since I’d seen they way she was looking at me. I let her kiss linger. It was soft and delicate in a way Matt’s could never be. It sparked a desire that took me to a very lustful place. I felt her hands pull me closer to her, the warmth of her skin on mine.
“Are you going to make love to me?” I whispered.
“Not now, Amy. But I am
going to. You are too delicious to pass up. I believe the boys have other things in mind for your first.” She cupped my ass then stepped back, a glimmer of conspiracy in her eyes.
She took the tray of drinks and before I could think of anything else to do or say she headed back up to the deck and the men. I pondered her promise to make love to me. I’d never been with a woman before and had never really thought about being with a woman but somehow the idea didn’t frighten or turn me off. Her kiss still lingering on my lips, I looked at myself in a mirror in the bedroom. Turning to the side I looked at my bottom in the mirror, the thong-style bikini leaving nothing at all to the imagination. I smiled, proud of my look and myself.
Returning to the deck I found the threesome sitting around the wheel and chatting. They were laughing and enjoying their drinks as we sailed north along the lakeshore. The day was perfect, sunny, and warm. Milo announced that we were sailing for a shallow patch of lake where the water was warmer and we could anchor the boat. A steady stream of 80s hits played on a boom box.
After sailing for about an hour Milo asked me if I wanted to steer the boat for a while and I took the wheel without really knowing what I was doing. He stood close behind me, wrapping his arms around me placed his hands on top of mine on the wheel. His musky cologne was just detectable in the wind.
“You just let the boat do the work, it’s not like a car. It just knows how to sail, you only need to hold on and enjoy it
.” Said Milo, his voice pitched so that only I would hear it.
“Are you enjoying it?” he asked.
“Fer sure. This is great.”
“Matt thought you would.” I could feel Milo’s body pressing in to my back a bit now, the considerable bulge in his shorts brushing against the mostly bare skin of my ass.
He dropped his hands off of mine and I felt him put them on my hips, over the ties of the bikini bottom. He pulled my hips back ever-so-slightly his cock pressed a bit more firmly into my ass, separated by nothing more than the thin material of his shorts.
“Ahhh perfect. We are here.” Milo announced to the three of us as he let my hips go.
Patting me on the ass he said “Jen, take Amy to the bow and get ready to drop the anchor. Matt, go drop the jib.”
Jen led me up to the front of the boat and prepared to drop the anchor. Milo told Matt to drop the jib, and then he let the main sail go slack. Taking this as her cue Jen let the anchor drop into the blue lake water. Looking out I could still see the shore, but it was far enough away that I couldn’t make out individual people or anything but larger buildings – most of which were probably apartments this far north of downtown.
When the sails had been stowed and the boat came to rest on the mild swells of the lake we had sandwiches and wine. The gentle rocking of the boat, the sun, and the wine all combined to leave me feeling very relaxed.
After finishing my food I walked up to the bow and found a nice place to lie down and get some sun. Jen joined me offering to apply some tanning lotion (as we thought of it back then). Without hesitating I nodded and wasn’t at all surprised when she reached over and untied the top to my bikini. She removed it, then removed her own and dropped them through an open skylight into the bedroom below. Her nipples were round, brown, and perfect – I was glad to hide my staring eyes behind sunglasses.
She started applying the coconut-scented oil to my skin. Her hands were soft and firm and the way she touched me was different than the way Matt would touch me. She knew how and where to touch me in ways that made me shiver. My nipples grew hard as she caressed them while smoothing the oil into the pale skin of my chest. It seemed like here hands were only on my breasts for a moment, then she was moving down to my belly, the smooth stroke of her hands relaxing me.
“You know they would love nothing more than a good show right now.” Said Jen, “What is it that you want?”
Her hands were now caressing the skin of my thighs, teasing me by running ever so close to the small triangle of cloth that covered my increasingly wet sex.
“I want what you are doing to me.”
Jen smiled, “So you wouldn’t mind if I did this?”
She tugged at the strings on my bikini bottoms.
I shook my head, too overwhelmed by what was going on to say anything. She tugged gently on the panties and I lifted my ass for her so that she could remove them, dropping them down the skylight. My pussy, void of hair after my waxing, was dark and I could feel the air move across my clit which peeked through my engorged labia.
Jen stood and as she wiggled out of her bikini she looked me over. “God, but aren’t you a sexy little thing.”
I blushed and spread my legs a bit for her, knowing that’s what she wanted but feeling just a bit unsure of myself as well. Jen kneeled down between my parted legs, placing her hands on my thighs again and sending a shiver through me.
I was eager to feel her touch and surprised by how much I wanted her, a woman
, to make love to me.
I’d been so wrapped up in Jen that I hadn’t noticed that Matt and Milo had walked up.
“Jen. My beauty. Would you like to smoke with me before you have fun with our new friend?” Said Milo.
We both turned to look at Milo who stood hulking above us both. He had a large joint in one hand and a devil-may-care smile on his lips. Jen nodded quickly and he lit the cigarette puffing deeply before handing it to Jen who followed suite.
She finished her drag and reached out with the joint, handing it to me. I was hesitant. I’d smoked once or twice before but had never felt much different as a result. I was worried that Matt wouldn’t approve and I looked to him for guidance.
Matt smiled. “Go ahead. I don’t touch the stuff but Milo says its good and you might like it.”
I took the smoldering joint, bringing it to my lips and inhaled deeply. This first drag was met with a coughing fit of unreal proportions which left everybody laughing at me, somebody quipping about how “even Amy’s body loses a little something when she coughs like that.”
The three of us smoked the rest of the joint and after a couple more puffs I felt my head spinning. When Jen handed me the roach for yet another puff I could swear I felt jolts of electricity flow between our fingers when they touched. Instead of taking another puff I handed the joint to Milo and turned to Jen. She instinctively knew what I wanted.
“Boys, why don’t you give us some space?” she said, never turning to look at the guys.
I don’t remember what they did. I do remember the tingle I felt when Jen’s lips touched mine. It started at the base of my spine and spread out into my belly, up my back, down my legs. I felt her hands put pressure on my shoulders, pushing me down on to the deck. Then she was sitting on my hips, her hands holding my face as she kissed me. I reached up putting my hands on her hips. She felt strange in my hands. I was used to holding Matt’s hips: flat and hard, the feel of muscle and bone. Jen’s curves were luscious, her skin soft, its tone supple and smooth.
Jen’s hands found their way to my breasts. My nipples responded to her touch instantly, hardening under her fingers. Her touch set of goose bumps, so light and gentle. She played with my nipples while we kissed. Our tongues danced with each other and I found myself moaning as she continued to fondle my breasts. I grew curious and slowly let my hands wander to her large, firm breasts. They were soft, inviting me to touch them, her hard nipples setting a delightful contrast to the soft smooth skin surrounding her dark red nipples.
Jen began to moan in to my mouth as well and I felt her hands slide down from my tits to my thoroughly soaked pussy. Her fingers traced the sensitive skin around my sex and then slowly opened my flower and slicked themselves in my dew. Her gentle touch found my clit and slowly she started playing with it in a way that I’ve never experienced with a man. She new just how much pressure and speed was needed and the delicate dance of her fingers on my wet, swollen sex sent my head reeling. I was quickly closing in on an orgasm when Jen stopped.
My eyes opened to see Jen’s naked form diving off the side of the boat in to the cool clear water of Lake Michigan. I felt disappointment flash across my face and my body felt as though it was deflating after being so aroused at her touch.
“She does that to almost everybody, including me.” I heard Milo call from the cockpit. “She’s left me blue so many times that I think I’ve suffered permanent damage.” He laughed. “Don’t worry though, she only teases. She is most certainly not a tease
Despite myself I shot Milo a look that suggested I’d kill him if he got any closer. This had the effect of making Matt break out in to roaring laugh as he punched his friend on the shoulder.
“Watch out my friend.” he said between belly laughs. “She’s far more dangerous that she looks.”
Shaking my head at the man-boys at the back of the boat I stood, peered over the edge and dove off the boat. I came up under Jen as she was treading water. Even under water she was beautiful. I yanked on her legs, pulling her down to my depth. Her eyes flashed surprise as she saw me, then smiled as we surfaced. We frolicked in the cool water, and I found the more-than-occasional touches that we exchanged to be incredibly exciting. After playing in the water with Jen for 10 minutes or so we climbed back on board on the aft swim platform.
The men were there to greet us with towels, though I ended up getting wrapped up by Milo as Matt took care of Jen. Milo gently, but quite thoroughly dried every inch of my skin taking extra time on my breasts and thighs. He took me by the hand and began to lead me through the cockpit, towards the main cabin. Suspecting what was going on I looked back at Matt, my eyes questioning him. He simply smiled and nodded his assent as he took Jen’s hand while watching Milo and I descend in to the luxurious master cabin. Once I’d arrived Milo picked me up and set me down on the bed, his barrel chest and massive biceps moving me like I was nothing more than an inflatable doll, there for his pleasure.
For the first time in my relationship I began to feel a twinge of fear. Something in Milo’s demeanor had changed and I felt vulnerable on this boat, in the middle of the lake, with two people I’d never met before today.
“Matt tells me that you are very obedient, is that correct?” he asked as he took off his shirt.
Knowing what was coming I grew nervous, my second lover would be a man who I hadn’t even met 4 hours ago. I nodded silently, looking at his tan, muscular and hairy chest.
“Good, I like obedient women. How many lovers have you had, Cherry
?” a sly smirk flashing across his face as he asked.
“Cherry” I thought to myself... Matt had told him about our adventure last night in the club. I blushed fiercely, probably turning a shade of red any cherry would have been proud to be.
“Ahhh, so only one. Well, from what Jen tells me, he is a very different lover than I am.”
Hearing this I’m sure my red blush turned in to a dark shade of green, the jealousy that Milo had just sparked. The thought of Matt having been with her made me upset, and drove me to the realization that they were probably in a very similar situation to the one Milo and I were in right now. I briefly contemplated getting up and walking out of the cabin, but changed my mind quickly. Matt had wanted me to do this. “Damn it” I thought, “I’ll fuck him like he’s never been fucked before, and let him tell that to Matt.”
I sat up on the bed and reached out to Matt who continued to look me over as though he were choosing which rib-eye to get at the butchers. I let my hands wander over his chest, its rough, hairy texture making him feel almost dangerous.
“Take my shorts off Cherry.” His voice firm, commanding.
I looked up at him, in to his eyes, as my fingers clumsily unsnapped the OP cord-shorts he was wearing. I’d hoped to find the same look in his eyes that I’d seen so often in Matt’s and more recently in Jen’s, but it wasn’t there. All I saw was cold and detached, increasing my belief that he was actually looking at me in exactly the same way he’d choose a steak.
My fingers unzipped his shorts and I slid them down his strong, legs. He was wearing a speedo-style, black swimsuit with a Perdue logo on the side. I saw the outline of his hefty shaft bulging against the material. My jaw dropped open as I realized that even though he wasn’t any where close to being fully erect, his cock was almost the size of a beer can. That vague feeling of fear blossomed a little, my mouth grew dry and I looked up at him.
“So he didn’t tell you about me, did he?” Milo leered down at me, seemingly enjoying the look of fright on my face. “Its almost 9 inches, and very thick as you see. Go ahead!” The last part coming in as a command.
“Ummm... I’m not so sure about this.” I looked up, hoping to find something gentle to reassure me, but nothing in his expression did.
“You will do as Matt told you. Do you understand that Cherry
I nodded, resigning myself to this encounter, not because I wanted to have sex with Milo. The only thing motivating me was my burgeoning love for Matt - I couldn’t stand the thought of disappointing him.
Reaching out again I slowly pulled down the speedos over his muscular ass, and legs, freeing his rapidly hardening cock which had a slight bend to it. Reaching out to touch him I wrapped both my hands around his shaft and squeezed, a few drops of fluid leaking from the tip. His skin was hot and dark, he had no tan lines, and his legs, butt, and crotch were all covered in thick black hair. I could feel him pulsing in my hand and the idea struck me that if I could finish him off in my mouth I wouldn’t have to find out whether or not I could accommodate him in me anywhere else.
I leaned forward and licked his head, the salty taste of his precum similar, but not identical to Matt’s. I heard Milo draw in a deep breath as I wrapped my lips around his head, and experiencing him grow just a big thicker each time his cock pulsed.
“mmmm, that’s a good girl. Now lets see if you are as good as he says you are.” And with that Milo grasped the sides of my head and pushed his hips forward, pressing his warm, and obscenely large cock deeper in to my mouth. I managed to open as wide as I could, but still was only able to take about half of him before I felt myself panic, as though I wouldn’t be able to breathe if he pressed in any farther. My panic and his insistent thrusts triggered my gag reflex, but the awful sounds that I made didn’t prompt him to stop, if anything he only tried harder to get me to take him in.
I tried grasping the base of his shaft, only to have my hands swatted away as if they were annoying gnats. My jaw was aching, my eyes watering as he finally stopped expanding, his fat cock now fucking my head as though I were an inflatable doll. I felt like I was giving up, caught between my love for Matt and the hard piece Milo was fucking my mouth with.
Finally he seemed to get bored with my mouth and pulled his saliva covered cock from between my lips. I felt a sharp click in my jaw as my mouth finally closed and started to mold in to its natural form. I looked up at Milo, wondering if he was done with me, but again finding no solace in his demeanor.
“Come Cherry, get on all fours like a good girl. Now I’m going to show you how a real man fucks some nice teen-aged cunt.” He chuckled as I moved to the middle of the bed and presented my ass to Milo.
“What a view!” he exclaimed. “I’ve got to taste that.”
It was the best thing he could have said, my fear had left me dry and I hoped that his oral skills would be able to get me stimulated enough to ease the passage of his battering ram. I felt his weight shift the bed and then felt his fingers slide up the backs of my thighs, to my pussy, and spread the lips as his tongue began to work it over. I pressed my face and chest to the bed, giving him a better angle which he immediately took advantage of.
His hands grasped the front of my thighs, and he pulled me back on to his mouth, this tongue furiously working me over. Despite myself and my assessment of his intentions I found myself moaning as his rather gifted oral talents. I knew I was getting wetter and wetter back there, and I felt my entire lower abdomen grow warm and begin to tingle. I was quickly approaching orgasm when I felt him stop.
“You taste like honey girl. I think you are ready for me now” he said, sliding a big meaty finger in to my pussy.
I felt the weight on the bed shift, and the palms of his hands grasped my thighs. The head of his cock pressed against my pussy, urgent and indelicate - prompting me to try and relax as much as possible. He pulled my hips back and my wet labia parted around his beer-can-cock. I knew immediately that there wasn’t going to be much pleasure in this encounter, at least not for me.
My intuition was dead right. As his phallus pressed deeper, spreading my delicate flower I found myself clenching my jaw and knitting my brows together, the unease of taking him slowly turning in to pain. I felt his ram completely fill me, his mushroom head pressed up hard against my cervix. He pulled himself out, my pussy quickly relaxing as he departed, then plunged himself back in, his hands yanking back against my hips powerfully. I moaned, more to pretend that I was enjoying it and have him feel satisfied, than by any actual physical pleasure I was receiving. He continued to fuck me like this for a few minutes, my tits jostling back and forth in time to his angry thrusts. I felt his cock twitch and wondered if he was done, and was relieved when he pulled out.
My relief turned to despair when he roughly flipped me over on to my back and pushed himself between my knees. It was much harder for me to see him, his hulking, meaty body that was sweating profusely in the stagnant, thick air of the cabin. His prick thick and club-like, now wet with my slick, pointing at me - as if warning me that I’d better toe-the-line or be ready for the consequences. He leered at me, then roughly pawed my breasts, pinching my nipples and bring a gasp of pain from my lips.
“Ok Cherry, now watch as that tender cunt of yours learns how to fuck a real man, a real cock!”
I couldn’t help but look as he took his organ pressed it to my pussy, flexed his jack-hammer of an ass and pushed in to me roughly with no regard for my experience. Once inside he sort of collapsed on me, his heavy sweaty body pressed tightly against mine, his cock pistoning in to my body filling me up completely and with every stroke leaving me feeling more and more empty.
As he began increasing the power of his increasingly rapid assault I started thinking back to my first time with Matt. I thought about how warm and tender he had been with me, his patience and caring as he’d made love with
me for the first time. I let myself drift off in a dream of our romance as this great hulk of a man used me for his own pleasure. I became so deeply immersed in my memories that I can’t recall much else about my experience with Milo.
When I came out of my reverie, I felt sore, incredibly sore. I had fallen asleep, and was lying naked and alone on top of the bed. The boat was moving as I looked around, re-orienting myself to the situation. Looking down I saw blood and cum drying on my thighs. I wondered where everybody was and hoped that Matt would come in and comfort me until it dawned on me that he might have been with Jen this entire time. Giving her a respite from Milo’s ungodly prick and reminding her just how good and tender love can me.
I dressed quickly, finding my bikini that Jen had dropped through the skylight, and then putting my shorts and shirt back on as well. I slowly walked up the stairs to the cockpit where Matt and Milo were sailing the boat. The weather had started to turn and storm clouds were rising to the north as we sailed south towards downtown. I paused, watching them for a moment... they were chatting cordially, and given some of the lewd gestures that Milo was making I felt pretty safe in assuming he was describing his time with me. He seemed quite pleased based on his body language.
As I hid in the shadows of the boat’s cabin, I saw milo reach in to his back pocket, remove his wallet, open it, and remove a fat wad of bills. He quickly counted them out, I saw several 100s, and handed them over to Matt. Matt took the money without counting it, and quickly pocketed it, shaking Milo’s hand vigorously after stowing the cash.
Wondering back to that day on the boat, I now question myself as to why I didn’t feel any jealousy, or anger at being passed off to Milo so casually. To be honest, I think I’d already started to understand my situation, albeit at a purely emotional level. I was growing to to understand what my relationship with Matt was, and would continue to become, and just how different that conceptualization was from what I’d thought it was when I first kissed my Swim Coach. I just wasn’t old enough, or should I say, ready enough to let my thoughts about us completely form themselves in my young, puppy-in-love mind.
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<a href="https://www.lushstories.com/stories/novels/swim-coach-chapter-12.aspx">Swim Coach (chapter 12)</a>