Getaway with My Bestie Pt. 01 – Erotic Couplings – Free Sex Story

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A few years had gone by since our last encounter. We still talked on a regular basis, but unfortunately it was not easy for us to see each other. We didn’t talk much about our prior escapades as we didn’t know how we would respond to those times. We would approach the topic almost in code to make sure that no one knew what we were talking about.

I hadn’t told anyone about what we had done, I kept that to me and me alone. I had a password protected file with all of the pictures and some of the more erotic messages sent between us saved if I ever wanted to use them for some self-pleasure, and yes, I did use them often. Occasionally as a treat you would send me some pictures and I did certainly Love those days! I eventually found out that you had shared with a mutual friend of ours, Jen, what we had done, and I was totally cool with that.

It was Springtime and it was a day like any other day. Normally we just texted back and forth, but today you called me. It was a rarity that I was by the phone, but I was excited to hear from you. You got right to the point. You asked me what I was doing for my birthday. I was a bit thrown off with the question but replied with a simple “I don’t know yet.”

“Want to go visit Jen?” Together, I asked foolishly, and you laughed and said, “well yes, of course.” You told me that you were going to visit her the weekend of my birthday and you chose that weekend hoping that I would be able to come too. She is also sending the kids to Grandma’s for the weekend so it will just be us three.

Absolutely, that sounds amazing I said! You told me that you had to go, but you would send the flight information later. Once I got the text I booked my flights, and I had a surprise for you as I had your confirmation number, I upgraded your flights to first class along with mine a couple rows in front of me as I didn’t thnk we should be sitting together.

I sent you a message that flights were booked and that I was excited. You sent back simply…”wait till you get there lol xoxo, talk soon!”

As it got closer, we timed things so that we wouldn’t be arriving at the airport at the same time. The day came to travel and I was packed, groomed, and ready to go. The next morning I woke up early, grabbed my bags and a cab to the airport. I brought some work with me and got through security obnoxiously early so that we wouldn’t cross paths. “Made it through security, see you soon” was the message I got. I was sitting at a different gate and whistled as you walked by.

I watched you walk up to the desk and you were showing the gate agent your ticket noticing that you were sitting in first class. I watched you take your phone out of your bag and my phone vibrated. Text said “Did you do that? Did you upgrade me to first class?” Happy birthday to you too lol, see you on the plane was my response.

I made sure that I got in line after you and as I walked by you sitting in the aisle seat I ran my fingers ever so delicately up your arm. The first message you sent me said that made you tingle all over! We messaged throughout the flight igniting our desire to be alone even more. The flights were smooth and we arrived at our destination. It was so Hot. I was waiting for a cab as I watched Jen pick you up at the terminal. You looked back at me and smiled as I got in a cab not long after and gave the address to Jen’s house.

I got out of the cab and I walked to the door. You met me with a huge hug and a kiss right on the lips, I dropped my backpack and embraced you as well. Didn’t want to creep Jen out and it had been a long time since I had seen her too so I walked over to her and gave her a hug and a kiss as well (on the cheek of course). You got us both a glass of cold water and we soaked up the air conditioning as you gave us a tour of the house.

We dropped our bags in our room, which was weird, but awesome to think about! Walked back to the decking off the back of the house and there was a nice set-up, Hot tub included with a very private atmosphere. “Damn it! If I would have known you had a Hot tub, I would have brought a bathing suit!” You both instantly giggled.

I don’t know what you had said to Jen on your way to the house or I was missing the signals you were sending her, but Jen simply stated “I will let you two get caught up.” As Jen walked away with a coy look on her face, you grabbed me by the hand and led me to the bedroom and quickly shut the door behind us.

No time is wasted! Your hands were on me quicker than I was prepared for and I lost my balance backwards. Good thing is that I am close to the bed and was very happy to pull you that direction with me. I fall onto my back and instantly your tongue is in my mouth and my hands are holding you by your Ass. “Get up” you tell me as you stand up. “Take off your clothes!”

I have never been so inclined to listen to orders. My clothes were off as fast as I could get them off and I crawled up on the bed with the feel of you slapping my Ass as I did so. The hottest thing I had ever seen was seeing you crawl up from the foot of the bed towards me on your hands and knees. Your tits were moving side to side beneath you as your hips moved in unison with them.

Lying on my back you straddle my hips and your pelvis comes to rest over my very hard cock.

You align your tits perfectly with my mouth and as you reach down to put me inside you I suck hard on your right nipple. Left hand massaging your other breast and my right on your Ass, you slide down until our pelvises meet, your Pussy gripping me fully now. I move my left hand to your Ass and start to assist in guiding you up and down on my cock. I feel so close to you at this moment and the urge for this has been building for some time.

I grab the back of your head and start to kiss you deeply. You never stop riding me and I can feel your wetness saturating my balls. Your torso begins to tighten and your strokes shorten. Your Orgasm overtakes you as you grind your clit against me, gyrating close to my body I tell you that I am going to come and I grab each Ass cheek hard and don’t let you pull away as I erupt inside of you.

I can’t contain myself and groan loudly as I release all that I had been saving for this very moment. You sit up tall with me still inside you and your flush chest and hard nipples tell me that you just had an amazing time. From the other room we hear clapping and a resounding “WOO HOO” from Jen.

You laugh hysterically squeezing me with your Pussy with every bout of laughter as you collapse forward on top of me. Kissing me on the neck you say “this is going to be one hell of a weekend, this is not the last time she is going to hear us FUCK!”

We stay in bed for just a bit to regain our composure and you quickly run off to the bathroom as I fumble to find all of my clothes. We come out of the room and look over to the couch where Jen is sitting and all she can do is laugh while she jokingly uses her fingers to say “shame shame.” I ask if you two want a drink and go to the kitchen.

While in there I hear whispering and some giggling, but when I come back out the both of you are all business. I sit on the chair next to the couch and we spend some great time catching up.

Evening rolled up on us and we decided to go out for a nice dinner together. It was a casual place that we had decided upon, but we all still tried to look our best. I went back to our room and showered. I put on a pair of dark colored jeans, slick black shoes and a French cuffed button-down shirt and waited on the couch as you both were in Jen’s room getting ready.

Much to my enjoyment you both came out in beautiful sun dresses you each had a damp look to your hair. Neither of you were in there for long and my perverted mind wondered if you had showered together. I didn’t ask, but I wondered for the rest of the night. You walked over to me and leaned in for a kiss. I could see right down your dress and saw that you were not wearing a bra.

Smirking at me you said “we don’t have anything on the bottom either.” “We” I questioned and a simple “yup” was all you said. We got into Jen’s car, I let you have shotgun and we headed to dinner. We ended up at a seafood restaurant and that was great as none of us were looking for anything heavy. We ordered cocktails and some apps to share and as we waited for dinner we continued to catch up like we had never been apart.

We were sitting in a booth, you and I next to each other, and Jen across the table. You were on the inside and I couldn’t help but caress your thigh under the table creeping higher and higher as the evening went on. Dinner was amazing and we decided to skip dessert for tonight. The check came and I grabbed it quickly. You leaned over and kissed my cheek and said you would thank me later with a grin. Jen got up to use the bathroom.

I was secretly hoping that a gust of wind would blow her dress up, but no luck with that! My hand was back on your thigh and as I caressed you grabbed my hand. Spreading your legs slightly, you pulled my hand to your crotch to let me feel what a dinner of caressing your thigh had done. You were soaked!

I dipped two fingers into you and pulled them out just as Jen was walking out of the bathroom. Quickly, I brought them to my mouth to sample what I was hoping to taste later. “I saw that” Jen proclaimed quietly as I slid out of the booth, stood up, and walked with the two of you out to the car.

You sat in back with me this time on the way home. Sitting behind Jen you pulled my hand back as you opened your legs and let me play with your Pussy some more.

Your head fell back against the headrest. Jen knew what was going on in the backseat, she was no fool, but Jen tried her best to focus on the road as you quietly came grasping my hand with yours. I pulled my fingers out of you and again used my tongue to clean them off. You closed your legs and put your dress back down as we were pulling into the driveway.

Back at Jen’s house we sat and had a night cap and then decided it was time for bed. We stood up and walked over to Jen giving her a hug good night. Whispering in my ear, Jen told me “have fun tonight see you both in the morning.” Jen kissed me on the cheek with a lingering touch and then we parted ways. We walked into our bedroom and you told me to take off my clothes and get into bed. You grabbed a bag and went into the bathroom, shutting the door behind you.

Laying in the bed for a short while naked and on top of the covers I turned on the TV. Flipping through the channels I heard the water from the Shower turn on for a short period of time. There was some movement, but eventually I heard the water stop and the door opened as you turned off the light. You looked magnificent. You were naked, you were shaved, your nipples were erect and you smiled as you walked to me.

“Look into the nightstand on your left” you told me and I rolled over to open the drawer my Ass now facing you.

That was “your” side of the bed while we were visiting and I was shocked to see what was in there. I bottle of lube, some coconut oil, and a moderate sized vibrator was in there. I laughed and said “are these for you or me” and laughingly you told me “both if I like it that way!”

You crawled up on the bed as I rolled back to my back with the vibrator and lube in my hand. You laid down next to me and snuggled up against my body. Your bare chest resting on my side and your leg now draped over mine my erection was growing you did not beat around the bush.

“What are your thoughts on Anal Sex?” My facial expression could have said it all, but I responded with a simple “I Love it.” Ok great you told me, “I was surprised you didn’t fuck my Ass that night we videotaped us. You and I both were loving having your tongue in there, I thought for sure when I told you anything goes I was going to feel you cum in my tight Ass that night.”

“Tonight, I need to you to fuck my Ass. I came prepared for this and it is going to be amazing.” I found out later when I went into the bathroom later that you had bought things to make sure you were super clean and ready. I also found out that Jen knew what was happening as she went to get the supplies you needed before we got there so you wouldn’t get caught having them before leaving!

My cock was now rock hard and pre-cum was leaking out of the tip. Just before I leaned over to kiss you, you grazed my head with a finger scooping up the moisture and putting it in your mouth. I could taste myself on your tongue.

I rolled you onto your back and crawled over you. I got off the edge of the bed and grabbed you by your bent legs and pulled you over. Since you liked it so much last time I told you to get on your hands and knees on the edge of the bed. You let your chest rest down on the mattress and your knees were slightly parted. Your Ass and lips were there for me, for my enjoyment. I grabbed your Ass cheeks opening you up even more and with a dee breath in for the both of us I leaned in to have my first taste from the source of the weekend.

Slowly and firmly I pushed my tongue against your Pussy parting your lips as I enjoyed the sweet taste of your nectar. I swirled my tongue around for a while before moving up further to your beautiful Ass. As my tongue began to encircle your Ass I put two fingers back into your Pussy and pressed down into your g-spot and began to curl my fingers and move them in and our of your Pussy as if I was fucking you with them.

My tongue pressed harder and eventually was able to dip into your butt just a bit and we both enjoyed that. You reached back with one hand and grabbed an Ass cheek pulling yourself even more open allowing me to explore even more. You began to push your hips back against my fingers and tongue playing with you. I am so hard, but I want nothing more than for you to enjoy this night too. I want you to cum over and over again! Your first Orgasm approaches and the damn opens, your body releasing moisture from your Pussy. My fingers and hands are soaked and I Love it.

It is good enough for to stop eating your Ass to clean up your Pussy with my tongue. You roll over onto your back and my onslaught to your crotch doesn’t miss a beat. I push your knees back opening you up now from the front and continue to lick the lips of your Pussy up and down, over and over again. I look up and I see you laying there with your eyes closed and your tits in your hands massaging your breasts and nipples.

The oil, lube, and vibrator have now been moved to the nightstand on my side of the bed and I stop kissing and licking your Pussy just for a moment. I reach over and ask if you like the coconut oil or the lube and you told me try the oil you had never tried that before. My head starts reeling knowing that Jen put that there for you and I tonight. I put some one my right middle finger and start to roll it between that and my thumb. I use my thumb and rub it gently against your asshole to coat it ever so slightly. I lean in for a taste and it was amazing!

My middle finger coated in oil I gently press against your waiting hole. You take a deep breath in and as you let it out I press forward letting my finger enter you to the first and then second knuckle. I don’t move for a while. I watch for your breathing to change and your body to relax. As it does I lean in and as I take your clit in my mouth and begin to suck I slowly start moving my finger in and out of your tight asshole.

My lips close around you and my tongue moves in circles around your clit as I hum and suck you into my mouth. Your first Orgasm was quiet, but you are getting louder and louder. Your breathing is labored and the pace of me finger fucking your Ass increases in its intensity as well. Initially I worry that Jen is going to hear us, but from the things said and reactions throughout the day I don’t think she gives a fuck at the moment and is probably cheering us on.

You cum, and you cum HARD! Your clit pulls from my mouth as your hips buck up towards my face. Your Ass begins squeezing me harder than I could have imagined! My left hand reaches up to play with your nipples and you push my hand away. My other finger is still deep inside you and as I begin to pull away you grasp me some more so I just hold where I am. We are both sweating at this moment and your body is red! You slowly start to come down off your orgasmic high and I pull my finger out of your Ass.

I semi crawl up onto the bed to kiss you and you are breathing quickly and between breaths you tell me how amazing I am. We make out for a short time and you reach down with your right hand and grab my thick cock. You look me in the eyes and remind me what we are there to do and tell me that it is time for me to have some fun too! Looking dead in your eyes I clearly express to you how much I have already enjoyed what we did!

Standing up I reach over to the night stand table and grab a copious amount of coconut oil and as it starts to melt, I begin to stroke my cock covering it completely in oil laughing as I now smell like a tropical drink! Walking back to nestle between your legs you pull your knees back as I use my hand to cover your Ass more with the sweet-smelling oil.

I place a large towel under your Ass as you continue to pull your knees back. I wipe off my hands cleaning the oil off as much as I can and align my cock with your waiting asshole. Rubbing the head of my dick against you I start to press forward. Slowly and with a calm look in your eyes telling me to keep going I continue to add pressure until just the tip of me enters you. You take a deep breath in and your chest heaves before falling back to the bed.

I give you time to get accustomed to me being inside you. I am holding your legs now as you are gently massaging your breasts again playing gently with you sensitive nipples. I push further in, not moving back out yet at all. I again want to take this slow. I want us both to enjoy this! One more push and I am now all the way inside of your Ass. My pelvis is resting against your Pussy and the feeling of your Ass grabbing my whole cock is like something I thought I could only dream of.

Slowly I start to pull back almost so my whole cock exits you, but my head is still inside and I press back forward again. I start to develop a rhythm while thinking of anything I can to keep myself going as long as possible. You feel amazing and your body is responding to me being inside you well! I look over to the nightstand and see the vibrator sitting there. It is flesh tone and looks like a real cock and I grab it. I can’t reach the coconut oil and neither can you, but I thought you may like the feeling of both my cock and the vibrator inside you at the same time.

“I have never done that before” you tell me and I ask if you want to try. A simple “yes please” comes out of your mouth and I think of ways to get it ready for you and finally say fuck it and put it in my mouth. Your Ass grabs me so hard as you laugh! I told you to be nice, I am only doing it with purpose! Laughingly you tell me that you never thought you would see one of those in my mouth and just so you know that is Jen’s not mine!

I honestly think that got me even harder knowing where that vibrator had been!

I pull out of your Ass as far as I could without coming out completely and reach between us to place the vibrator against your waiting Pussy lips. You are so wet, there was no need at all for me to put that in my mouth first. The vibrator slides easily past your lips and into your Pussy. I am now holding it by the base and while it is all the way inside you I join it by pushing back all the way into your Ass.

It is now your turn again to hold your legs back as I begin to match my thrusts with my cock and vibrator so that you are now getting fully double penetrated in both holes. Immediately your body reacts to it so fiercely that your next Orgasm is getting closer and closer. I myself have been aching to cum since you bent forward and I saw your tits behind the fabric of your dress.

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