- 1 month ago
- 9 min read
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I walk out of the hotel and hear for the pool. I am in a nice bikini and my am filling it out quite nicely. My A cup boobs push the black fabric out and rub my nipples with just enough tension to give them a semi hard appearance that pokes outward. I’m 5’8” and have a petite and skinny frame. I have my skirt on and high heels. I can feel the eyes on my as I walk to the pool and settle in to sunbath the afternoon away. I undress and lube up with sunscreen.
I layback and doze off into a lazy summer afternoon vacation nap. I wake to the waiter asking if I would like a cocktail and I order a water and a margarita, what the hell, I’m on vacation! I chug some water and pour a little on my towel and dab my forehead and chest, cooling it off from the hot sun baked kiss.
I sip my Margarita and a woman next to me says, “That looks refreshing!” And I quickly reply, “You have no idea!” She introduces herself as Rachel and I return with Carrie. She is one chair away and we chat about the resort and the weather and the fun we are having. She asks if I am there with anyone and I say no. She is here with her girlfriends who are on a booze cruise right now. We order another Margarita and continue our talk. The afternoon burning away and a slight buzz filling me up. I excuse myself to go to the bathroom and wrap my bottom and put on my seersucker shirt. I return and Rachel has moved a chair closer due to the increasing crowd that is gathering for the upcoming Happy Hour. I keep my wrap and shirt on as the sun is cresting to late afternoon and we order another drink since its Happy Hour now.
We chat some more and she says her friends texted that they are hammered at a bar downtown and won’t be back for dinner. She asks if I am interested in joining her and since I have nothing better to do, I accept. We finish our drink and the sun is setting, we head to the beach to watch this daily marvel and then head to our rooms to change.
I shower up and clean the suntan oil off of me and notice that I got some good color today! I rub some lotion on my sun soaked skin and put on a nice pair of pink lace panties, a matching pink lace bra, a light blue seersucker button down where I roll up the sleeves and a Maui Moonlight skirt paired with leather sandals. I do my hair up and spend extra time doing my makeup, not too much but just enough. I look at myself in the mirror and decide I need one more button undone on my shirt to expose my tanned cleavage and my green sea glass necklace. I spray some Tom Ford Fucking Fabulous perfume on my wrist, rub it into the other wrist and then rub my neck, then squirt a bit up my skirt not knowing where the night may take me.
I meet Rachel at the pool bar and she is already into a Tangueray & Tonic. It looks so refreshing, I order one too and we map out our plan for dinner. We settle on Pepe’s which seems to have a little of everything: Seafood, Steaks, Chicken, Salads. We finish our drink and walks to Pepe’s. Rachel looks cute in her orange pattern sundress and has her blond hair pulled back in a ponytail. She smells like tangerines and I like it.
We nosh on dinner and talk about our lives. No boyfriends, great jobs, good career future, healthy families, and the such and I find myself with a growing attraction to her. On the walk back, she grabs my hand and I am happy the feeling is reciprocated. We have a night cap at the pool bar, I have another Tangueray and Tonic and Rachel opts for a Rose. Feeling a little tipsy, I stand up and ask Rachel if she would like to walk me to my room. Thankfully, she agrees and we head up to my room. At the door, I fumble with the key card from my Louis Viutton clutch and Rachel puts her hand on my arm. I look up at her and her lips are on mine and we embrace in a hug and kiss for a moment. I ask her if she would like to come in for a drink and she eagerly agrees.
I open the door and grab two Miller Lites from the mini fridge and excuse myself to use the bathroom. Rachel picks around my room and checks out the souvenirs I have bought. I finish in the bathroom and decide to slip into my Kindle pink satin robe naked. The satin robe is super cute and comfy. I walk out and Rachel immediately turns around to greet me and says, “Wow, slipped into something more comfortable huh?”, and I reply, “Yeah, needed to get out of that skirt.”
“Where did you find this?”, Rachel says as she holds up a sand dollar necklace. “The street vendors that were here on Monday”, I say and she says, “I love it!” And places it back on the nightstand. She sits on the bed and I casually walk over and stand in front of her. She rubs my ass through the satin robe and I stand in front of her playing with my green sea glass necklace near my bronzed cleavage acting as coy and shy as possible but loving the attention I am getting.
Rachel leans in an wraps her arms around my waist and nuzzles my abs. She pulls slowly back and undoes the robes tie and opens me up like a Christmas morning present and is super surprised to see my 3” soft cock laying there.
She looks up at me in surprise and takes it in her hand and begins to rub it and I pull her up to me for a kiss. Rachel continues to stroke me and I can feel the stiffness overtake my once flaccid cock. She whispers in my ear, “What a nice surprise! I had no idea.”
I carefully undress her down to her panties and bra and begin to massage her slit through her panties. I can feel the moistness build the more I rub. Rachel is still stroking my now hard cock and I unsnap her bra and toss it aside. I work down and begin to suck her nipples and she throws her head back to give me open access to her beautiful tits. I tug downward on her panties and Rachel helps me out by shimmying her hips and the panties fall to the ground. Rachel pushes my robe over my shoulders and it falls to the ground.
Both naked now, I gently guide her to the bed. As we lie next to each ot her kissing Rachel works her way to my breasts and begins sucking my nipples bringing them to hard in a second. She confuses down and takes my cock into her mouth. She goes right to the base and then slurps back up. Sucking me off while rub my nipples in pleasure, I reach down and pull her leg toward my face. She straddles me and her beautiful mound is in my face. A slight wetness has crept out of her pussy and is glimmering in the soft light of the room. I dance around her labia’s and play with her for a while as I try to build the excitement of the moment. I take my time and I can feel her pull away when she gets a bit too excited from my foreplay. I work my finger and unhook her clit and give it a quick suck. She pushes her pussy onto my face enjoying the final release of pent up sexual energy she was craving.
Rachel works my knob over while I eat her glorious pussy out. Sounds of slurping and sucking combined with moans of pleasure from both of us. I am banging her with two fingers and and sucking at her clit and she releases a mighty orgasm that paints my face in clear coat. Sweet and savory cum that I enjoy greatly. Rachel pulls off of my face and turns and gives my cock one last lick before sucking and licking my body from cock to abs to tits to lips, paying attention to all of them and driving me wild in the process!
I roll her over and she spreads her legs and my cock is soon pressed up against it. It takes just a quick adjustment of our bodies before my tip finds the inside of her cunt and I glide in easily. I work her over hard at first and she cums within a few minutes and I bang her G-Spot. She helps me out by rubbing her clit to assist with this quick wave of orgasm and the added wetness feel great as I slide into her slushy hole with ease. I slow down now and retract for fear of cuming too soon but Rachel has other plans.
She rolls me over and climbs on top and inserts my 5” hard cock into her. She works me up and down and I reach her nipples and give them a gentle twist, Rachel reciprocates on me. The pleasure intensifying. In between thrusts, I pant, “I’m gonna cum!”, and Rachel reaches behind and squeezes my balls and tightens her pussy around my cock. I release inside of her and can feel my warm cum coat the inner walls of her pussy.
She pulls off of me a bit and I grab my shaft and squeeze every drops out of me and see some of it leach along the shaft of my cock before hitting my hand. Rachel pulls off and dab more of my man sauce plops out onto my stomach. Rachel rolls over and we kiss, as I stroke my cock a bit. I scoop up the dollop of cum and bring it up to eat and Rachel pulls my hand to her mouth and licks it clean. Sucking on my fingers to get every drop in between.
I give her a long kiss and can taste me on her and then I go down on her and clean me out of her. The mixture of our cum is sweet and sticky and I rub a little against her clit and she cums one last time. I savor her sweetness and return to a kiss. We fall asleep in each other’s arms. The rest of our vacation was spent together and none of her friends could tell I was a man. My outfits are so feminine, I love dressing as a woman and do that when on vacation. I am not sure what Rachel ever told them and we continue to be friends. Hoping to meet up again soon!