So, I decided to treat myself for the weekend with a friend of mine, Luis, by spending it in Martha's Vineyard. Neither of us had been there and we decided it would be a fun place to go as two single guys at this time of the year. We rented a room for the weekend, two bedrooms, kitchen, living room with a fireplace (not that we would be using it during this weather) and a 4th floor balcony porch.
So we spent most of the time at the beach, going around town, enjoying the bars. Its a remarkably friendly environment. Everyone was very friendly. So I decided one afternoon to go down to the beach while Luis rented a motorcycle and cruised around the island (I pride myself on my driving, but a motorcycle is a little outside my preparation level).
While I was on the beach, I noticed 2 women taking pictures of themselves in that typical hand-outstretched pose of trying to get both of them in the shot. The first was this very striking redhead, with a pair of unbelievable legs. Sitting on her blanket, you could just tell that those legs are in heels every chance she gets. She was in a black biniki next to her friend, a brunette who was in a purple bikini and equally as beautiful with this incredibly bronze skin. You would almost mistake her for latin, except for her face. But her skin was incredible looking. I decided to walk over and offer to take their picture. They posed for a few shots and I asked if I could pull up my blanket and join them.
We exchanged pleasantries, and found out that Lola (with the red hair) and Gretchen (with the brown hair and dark skin) were from Canada on vacation. We sat and flirted for about an hour or two, they didnt have boyfriends (though Lola eluded to being somewhat in a relationship, but stated that all was fair when you were out of the country) when Luis called and I told him that he should come join us. Luis joined us and we went into the water, engaged in a laughing game of chicken (I was not complaining when Lola mounted my shoulders) and spent the better part of the afternoon in the ocean. We agreed that we should meet up and go into town later. We gave them the address to our hotel and dropped them off in my car and went back to pick up Luis' rented motorcycle.
At about 6:30pm, the girls suprised us at our hotel with a few bottles of rum and some mixers. Both women looked absolutely amazing. Gretchen had on a gold top that d****d down very low in the back to show off her incredible skin and black pants that appeared to be some kind of leather. Lola had on high heeled thigh high boots, a black mini skirt and a white party blouse that was buttoned dangerously loose. They told us that they had wanted to "pre-game" before we left and decided to surprise us a little early. I was thankful I had prepped a little early with favorite white and blue striped button down and my favorite pair of jeans. Luis was about half ready, but with his latin background, he always seems to look great to women whether its a pair of sweat pants or a suit.
We pulled up a coffee table into the center of the living room and came up with a silly drinking game with a base set of rules that we ended up violating almost immediately. It was obvious that Luis had his eye on Gretchen, and being a GREAT appreciator of redheads, I was more than happy to slide closer to Lola. Gretchen (after stopping the game) very suddenly asked, "So is it true that Latin men are better kissers than others?"
Luis, always the faithful wingman, offered up, "Well, I suppose you can try both of us and contrast and compare."
Gretchen almost dove on Luis and buried her fingers in his hair, while Lola took her delicate bracelet covered hand and motioned me over. I took her by the small of her back and pulled her into me while holding the side of her face with a gentle kiss to her lips that increased in intensity very quickly. I felt her hands all over my scalp and ass. Her tongue had a life of its own and made for a very messy kiss (which gave me the distinct impression that we werent going anywhere that night, which was fine by me). We eased back and seperated our lips while I leaned in to give her ear a playful lick and she shuddered.
I looked over in time to see Gretchen pull her hand out of Luis' pants and smile, she then crawled towards me and Lola motioned for Luis to come closer as she had done with me. While Lola's kiss had been fiery, Gretchen was pure lust. She grabbed my wrists and pulled me into her top while I kissed her mouth savagely. I pinned her to the floor, feeling her leg go up around my waist and pulling me into her deeply. She moaned while I ground my hips into her roughly. I have to admit, I put far less finese into this kiss, and more raw need mirroring her own lust. She pulled away and bit down on my ear, licking the side of my face and clawing at my back while I felt my fly unzip. She gripped onto my cock and kissed me again, squeezing my thickness. I felt the heat from our bodies magnify, as her grip eased and she lifted herself out from under me and pulled away. I was left panting and wanting more.
Luis and I were left, partially undressed and sitting there, waiting for their next move. Gretchen poured four more drinks and then looked at Lola and said, "I don't know. I like them both. I think we need to do more.... thorough testing."
Lola smiled, looked directly at me.
"I want to see if he can fuck me as hard as he kissed me."
I smiled at Luis and we went to our respective beauties, sprawled out on the living room floor, inviting us with their incredible appetites. Approaching Lola, I held my hand out. I was dying to see her on her feet again with those boots and those incredible legs.
As I lifted her, she leaned into me, this smokey smile on her face the whole time. Her make-up was applied perfectly and the look on her face just screamed, "Come on... do it... I dare you."
I went to work on her ears and neck first. I've always been incredibly attracted to a woman's neck and I love the reactions to some delicate ear kissing. She did not disappoint. Her head rolled back and she started to make deep moans in her throat while burying her fingers in my hair. I could feel my cock harden further against my jeans, fingernails on my scalp drives me crazy in the best way. She smelled like sand and soft perfume as she made small nips at my fingers when they came into reach. My right arm moved to the small of her back. I only hope that she expected me to touch her fantastic ass, but I think I surprised her when I pulled and lifted her incredibly light frame up against my body so that only her boot-tips touched the ground. She immediately began kissing me and working my shirt open.
Behind me I could hear Gretchen slurping noisily away on Luis' cock. Within a few seconds, Lola had my shirt peeled off and was devouring my skin with kisses, licks and soft bites. I took the opportunity to unbutton and slide my jeans off, admiring her incredible form. Her skin was a soft white compared to Gretchen, with just a hint of a tan. A perfect contrast to her scarlet mane of hair. She was the image of an irish goddess. I looked over to my friend. Gretchen had wasted no time in stripping him naked and pinned him to the couch as she feasted on his cock and balls. Lathering every inch of skin with her tongue, noisily slurping and sucking him while rubbing her clit.
My attention on the spectacle on my left didn't last long however as Lola had worked my shirt and pants off and was slowly taking her time getting the outline of my own cock from my boxer briefs.
I decided to take some of the control back and lifted her back up to my level and turned her body away from me. From this angle, we were facing a mirror across from the couch, allowing her a view of the two of us, plus the incredibly sexy blowjob occuring behind us that was turning into a 69 quickly. Moving Lola's hair to the side, I begin to kiss across her shoulders and took the edges of her blouse in my hands. Eager to try something that I'd always seen, and being still tipsy from the booze earlier, I gave a sudden yank from both sides, spllitting the blouse (luckily, it was snaps, and not buttons, oh well) and revealing a delicious lace red bra underneath, clasping Lola's gorgeous breats. I ran my hands across the fabric, so that I barely touched, but it was obvious that her nipples were already incredibly hard. I trailed my hand lower to the belt and side zipper of her skirt and un-did them both. I let the skirt fall to the ground, leaving this incredibly beauty in her matching red bra and thong and her thigh high boots. She was the picture of raw sexuality.
The juxtaposition of her smooth pale skin against her red bra and thong, along with her scalet hair, coupled with the two writhing forms behind us was driving us both into an obvious sexual frenzy. Lola was grinding her ass against my cock, almost to the point pushing my boxer briefs down. I let one hand fall to my hip and began to pull them down myself. Discontent with letting me have control over any of my clothing, Lola spun and yanked them down to my ankles and in one swift motion engulfed my rock hard member in her warm, wet mouth. Her method was much more focused and purposeful than Gretchen's appeared. Her licks were decisive and aimed at specific points. Her tongue was a lethal weapon and I knew I was totally at her mercy. As far as blowjobs went, she was aggresively working her way to the best I had ever received. She licked the head until it had a thin sheet of saliva and then sucked deeper. I felt her tongue explore every inch of my shaft, licking and dabbing her way down further and further down. Her throat contracted around me, but she kept moving further. Her eyes looked up at me as she swallowed further and even though her mouth was filled, she still managed to smile mischieviously. I couldn't help my head falling back as my fingers lost themselves in her hair. I felt her tongue extend slowly down my thick shaft, her throat on the edge of gagging as the very tip touched the edge of my balls. I moaned loudly as her hands gripped my ass tightly, pushing me into her, unbelievably trying to f***e more of her delicious mouth down on top of me. She then began to withdrawl, a long, sticky sheen of drool left behind as she smiled and began to lick my balls, sucking each into her mouth and tonguing it within.
Behind me, Luis had freed his cock from Gretchen's furious mouth and had scooted himself under her, leaving her on her hands and knees on the couch while he had free access to her hungry pussy. He alternatively licked and fingered his way deeply into her snatch and she howled and screamed.
I wasn't surprised to discover that (thus far) she had the dirtier mouth of the two. Demanding him to, "Make me cum baby!! Finger fuck that pussy like you've wanted to all day!"
I looked down at Lola who smiled at her friend's naughty declarations as she continued to lather my balls and shaft, while also taking the time to explore the underside of my cock and teasing my asshole in a playfully taboo manner.
I was dying to sample Lola's pussy, but she was putting me into sheer nirvana with her mouth. I lost myself in her licks, sucks and tastes. Her tongue was a blanket of bliss as my head rolled back and forth. I was only aware of her mouth on me and my fingers in her smooth mane of hair. After what felt like far too short a time, I f***ed my brain out of its selfish mode and withdrew my soaking wet cock from Lola's mouth, a thin string of drool and precum dropped to the floor and her chin. I layed her down on the couch, within reaching distance of the squealing Gretchen as Luis pounded his fingers into her deeper and deeper. I couldnt tell but it looked as though he had two, possibly three fingers impaled in Gretchen's bald pussy. Her juices were apparent on the couch as she bucked up and down on his hand and mouth. Lola reached over to her friend's tanned body and began to run her fingers down her flawless skin as I inched her thong down past her knees and boots. Her scent was intoxicating and I tried my best to be as delicate and purposed as she, but I know I failed. I dove into her thighs and inhaled the sweet smell of her juices and sweat. Her bald pussy was as smooth as silk but literally dripping into my mouth. Her clit was larger than I had had before, and I gleefully licked it, sending moaning spasms up her body. Each time, she reached out to squeeze Gretchen, who by this time was clearly into her second orgasm as she gripped the pillows of the couch. I decided to do some fingering of my own as I licked two digits and ran them over Lola's lips. She sucked down on them, just as she had with my cock, and my mind almost clicked off again. I dragged my slick fingers down her chin, down her neck, across her breasts, over her smooth stomach, tickling the piercing in her bellybutton before giving her a wicked grin and slowly pushing them into the folds of her pussy. Lola was absolutely soaking wet. The fact that she was practically gushing empowered me further as I drove my fingers back and forth, all the while keeping my tongue firmly pressed against her clit. Her whimpers and moans were getting louder and I felt her body lurch as Gretchen grabbed her bra and tore it off as Luis mounted her from behind. From Gretchen's position, it put her directly over Lola's breasts as she took a nipple directly between her lips.
It was hard to gauge, but I had to guess that this was the first time Gretchen had ever done this, at least with Lola, because Lola's whole body suddenly stopped as she looked at Gretchen with sheer surprise that soon faded to blissful ecstasy. I caught Luis' glance for the first time since the escapade had begun and he looked like a cat who had just trotted into a aviary. His one hand firmly placed on Gretchen's exquisite ass, the other pushing her neck towards Lola's now nude (except for her boots) and writhing body. Surging with lust, I only was aware of two things, the delicious feel of Lola's pussy against my invading fingers and tongue and the fact that my cock wanted nothing but to plunge into one of these women and give them the fucking of their lives. Lola's bucking and clawing at my back became even rougher and more rushed.
"Oh god, don't stop. Don't fucking stop. I'm going to cum all over your face you bastard. God, don't fucking stop!"
More than happy to oblige her, I continued my actions, but going deeper into her loins and licking her clit more insistently. Her nails digging into my scalp and back as her boots lifted her hips further into my hungry lips. Feeling her juices start to flow, I impaled my fingers as far as they would go inside of her as I did my best to continue licking her throbbing clit as her hips bucked wildly. As her orgasm began to slow, I had a chance to glance to my right and saw Gretchen pounding back on Luis' hips while he pulled back on her hair. Her dark locks tangled in his fingers as she wildly screamed and cursed at him. He was clearly having the time of his life with her and she didn't seem to be too bad a time herself. I was curious if I'd get a turn with her later on, but I was more interested in the gorgeous, panting redhead in front of me.
I looked down on her, sweating, panting, hair spread across the cusions of the couch, and Gretchen's nail marks and lipstick across her breasts. "Ready to give those two a run for their money baby?"
"Fuck me like you're never going to see me again. Because if you don't do it right.... you won't."
I love a woman who presents a challenge.
I took her hand and pulled her into me. We kissed wildly, our faces a mash of tongues and lips, bites and licks. I grasped her thigh with one hand and lifted. The cool leather under my fingers feeling devine. I could feel her pussy juices drip onto the head of my cock as my rock hard erection found its way under her. I pressed my hips up, encountering some slight resistance despite her soaked condition.
"Fuck me... do i!" She wailed into my ear.
I could feel her bite my shoulder as I pushed further, her lips opening to accomodate my girth. Harder I pushed, nearly lifting her off the ground as I heard her inhale deeply in a noiseless gasp. Then finally, pop! The head broke through and my throbbing dick pushed further and further into her velvet tunnel. She was incredibly tight around me and she was feeling it.
"Christ, and I thought my boyfriend was thick. Fuck me baby. Give me that dick!!!"
I knew it!!! This new information coupled with the incredible pressure of her pussy drove me to grabbing her other thigh, leaning back and lifting her body into the hair, bracing her weight on my chest. Her leather clad calves wrapped around my back as I lifted and then dropped her down on my cock. Her scream broke the concentration of Gretchen and Luis behind us. Luis slowed for only moments before continuing his ravaging of Gretchen's cunt.
"You go you little cheating bitch. Let him show you how you need to be fucked!" Gretchen screamed towards Lola as I made a mental note to ask about it later.
With Lola completely off the ground and impaled on my cock, I started bouncing her mercilessly onto my cock. Dropping her harder and harder each time. Each time, her screams growing more and more into enraptured bliss. My own sexual fervor was driven wild by this fantastic redhaired goddess, clad only in her boots, fucking my cock up and down, and knowing that this was more than her boyfriend had ever offered her. Is there any faster way to a man's heart than through his ego? I spun us around and pressed her back against the wallpaper and pinned her between the wall and my body, her hands gripping to my back tightly as I slammed into her over and over again. I felt her shake and orgasm again as we grinded against the wall, I knew my own orgasm wasn't far behind.
"Get on your back! Do it!" Lola demanded as I fell onto the floor, carrying her with me. Knees braced she began to ride me with double the pace that we had matched before, each pump was followed by a, "Fuck! Fuck! Fuck! Fuck! as she rode me into my first impending orgasm. I was way beyond the point of being capable of asking her where she wanted me to cum, but from her fervor, it was fairly obvious.
Gripping her hips tightly as she bucked and threw her hair back and forth wildly, I felt my cock lurch deep inside her and explode in a torrent of cum, erupting into her pussy with rope after rope of hot stickiness. "GOD YESSS!!!!!" we both screamed. I felt my cock slowly slip out of her as Lola fell to her side, shuddering and shaking. Behind us, Luis and Gretchen, who had clearly finished during our escapade were collapsed in their own tangle of limbs, watching. Gretchen, a still hungry expression on her face crawled towards me and began to stroke my cock insistantly while licking Lola's and my juices off the head. Her lips felt devine and hot. She seemed possessed to get another load for herself out of me and if she kept going at the pace she was, she would get it.
Lola crawled over to Luis and mashed his face into her pussy. I have to give him credit for shutting out or ignoring what had just happened between she and I but he began to lick and finger fuck her like a champ.
I had to admit that Gretchen's rabid need for cum was an incredible turn-on as she pounded my cock in her fist, licking and drooling all across my hips and shaft. She could by no means compare to Lola's skill, but after Lola had worked me up into the state of sheer a****l desire I was in, a nice, sloppy, wet blowjob felt like just what the doctor ordered. Her mouth felt like wet fire as she sucked and gargled down every inch of me. I felt her free hand against my leg mercilessly rubbing her clit. The woman could give lessons in multi-tasking. She bowed her head below my shaft and began tickling my balls and the underside of my cock with the tip of her tongue, moving lower and lower. Ooooh, was this little devil going to go where her friend had only earlier just teased with exploring?
Gretchen's smile screamed of mischievious intentions as she licked and withdrew, licked and withdrew. She could tell the effect she was having and it was obvious she was loving it. To our left, Luis appeared to have Lola into another orgasmic spasm as his fingers plowed into her. Was he fingering her ass as well? I couldn't tell, but it certainly looked like it from the angle of Lola's hips thrusting upwards.
Gretchen continued to lick and then moved up to my ear, "You taste yummy baby. Is that all you or do you think its a little bit of her too?"
She withdrew from me and plunged her tongue again under my cock and skirted my asshole. My feet planted on the ground and I lifted my hips to her face as she continued to pressure my hips down with her strokes. She was gushing on the carpet and it was probably one of the most erotic things I had been a part of. I felt her tongue on the budding edge of my asshole as she licked away with sheer enjoyment as I moaned and sputtered out demands to match her own filthy mouth. It clearly egged her on as she bathed my asshole with her tongue, putting slight pressure on me but then comensating with more f***eful strokes on my shaft. I was completely at her mercy. The room was filled with the combined wails of Gretchen's muffled moans, Lola's screams of pleasure and my own declarations of need. I felt myself ready to cum again, this time more of a need than a desire. I felt my cockhead start to squirt into the hair as Gretchen pistoned her fist up and down onto me, her tongue still pinned under my ass. I felt the first rope release and her mouth followed soon the catch the rest. I sprayed into her face, spasming on the floor as Gretchen and Luis brought Lola and I to orgasm nearly simultaniously. Gretchen was the picture of filthy lust. The perfect Ying to Lola's yang as she fell back on her friend smiling. I wasn't even aware that she had cum. The room was filled with panting and deep breathing and the smell of sex.
I started to chuckle. "So, any conclusions ladies? Did you get the research you needed?"
Gretchen, unsurprisingly was the first to respond, pulling herself into Luis. "I'll let him eat my pussy any day of the week, but I think I'd end up cheating on my boyfriend too if I had a chance with your cock. What do you think Lola?"
Lola, whose voice sounded hoarse from the shrieking locked her eyes with mine. "I have never been fucked like that before... ever. How long are you both staying?"
Luis took the words out of my mouth, "Long enough to show you that I can match him with whatever you ask for. And long enough for him to try and prove me wrong." Like I said, he's a good wingman, and we still had a day and a half left.