Learning to Let Go

I took a seat in the bar, just as he had instructed. Nervous but excited, I looked around, wondering if he was already here. The bartender came to get my drink order and I ordered a glass of wine hoping to calm my nerves. The outdoor bar provided an evening breeze that swept over my body.

I was wearing a sundress, just as he had asked. White linen, it was form fitting around the breasts with a deep cut and flowed out from there, ending above the knee. The straps helped keep my 36D chest high and dry. My skin was tanned from a weekend at the beach and I left my hair curly to expose the sun highlights. My toes were painted and I wore my wedges to show of my long, tanned legs.

Halfway through my wine, I caught movement out of the corner of my eye. My heart beat quickly as I felt his breath on my neck. "That's my girl. What a good listener you are." I turned my blue eyes to him and was pleasantly surprised with what I saw. I was expecting some dirty old man, or some young perverted kid with his friends- but it was a man. A good looking man, just like his pictures. I met Scott online one night when I was feeling especially lonely. We talked often and I felt a unique connection with the way he spoke to me. He dove into my desires, boldly and with no reservations. He asked me to do things I had never done to myself before, and instructed me to do them with the webcam on. Scott had seen me explore my body in ways I had never knew existed.

After a year, I needed to either put this relationship behind me, or take it to the next level. We had exchanged pictures, but he never was on webcam as I was. It was a chance I took, and in the end it paid off. The plan to meet was now, and my excitement for the things I would experience swirled in my head, consuming me.

He sat next to me, ordering a double Crown on the rocks. He turned towards me after a long pull and moved the hair off of my shoulder. Moving in close again, he breathed in deeply and exhaled as he pulled away. "You smell better then I could have even imagined Brooke." I smiled and blushed at the same time. "Even better, you look more innocent in person then your pictures convey. No one in this bar knows what a dirty little slut you want to be." He told me to finish my wine as our night was about to begin. I sipped my liquid courage. "Brooke, I told you to finish your wine." Looking at him, I threw back my wine in one large sip. "Good girl." He threw back his drink in the same fashion and swiftly threw down cash to cover the cocktails. "Time to go." I grabbed my purse and walked towards the stairs. He didn't walk next to me but he lingered behind. I wondered if my legs enticed him, if my back looked tan. I walked down the stairs and as I exited the bar, I felt his hand on the small of my back. Without any verbal cues, I let him guide me. We walked for what seemed like a while, getting further into a residential area. I wondered if we were going to his house. The houses began to seem further apart as we followed a path. The path lead us to a playground. Scott sensed my hesitation.

"Do you trust me?" he asked me. I looked around, it was dark with some light being cast by the moon and a light pole a few hundred feet away. I could clearly see Scott's face, and by looking in his eyes, I knew I had no reason not to. "Yes," I answered nervously. "But, I don't get why were here." He guided me to the middle of the playground. "You know that you are here to please me, and be pleased. Don't question why, where or what, it will ruin your enjoyment." With that, I let my guard down to him, although I still couldn't figure out what he was aiming to do. We had talked about using the bar bathroom to fuck, so the change of scenery confused me.

We were close to a bridge connecting two points of the playground, and he moved me closer to the edge of it. He took the straps of my dress and pulled them down off of my shoulders, meaning for it to fall to the ground. Panicked, I grabbed at my chest, keeping the dress up, but barely. "Brooke, either you allow me to do this my way, or we part ways. I thought you wanted this?" Looking up at him, I let my dress fall, exposing my strapless bra and lacey panties. I moved to take my wedges off but Scott stopped me. "Leave them on." He picked up my dress and hung it on the pole. I stood unsure of what to do. Scott came towards me and unhooked my bra, exposing my breasts in the moonlight. He placed it on the same pole. He unzipped his pants, exposing his soft cock. "Get on your knees Brooke. I want you to get me hard in your mouth."

I got to my knees in the sand of the playground and ran my hands up his legs to his cock. I pulled it out, and wrapped my lips around it. It instantly made me wet. I slowly and seductively sucked his dick, feeling it grow in my mouth. It grew and grew, before I knew it, he was fully erect. 8 inches long and almost 2 inches around, I had a hard time getting it all in my mouth. I made sure to use my hands and open my throat to allow him to drive it as deep as he could. I gagged on his shaft but tried to recover as quickly as possible. I looked up at him, watching him enjoy my mouth. I moved both of my hands to his shaft and focused my mouth on his balls. Gently tugging and licking, I heard him moan. I knew I was pleasing him, but wanted to do better. I softly took my tongue and started at the bottom of his shaft, licking the length of him and wrapping my tongue around his tip and starting all over again on the opposite side. I could hear him grunting as his hips started thrusting. I used my mouth and opened my throat as much as I could- inviting him to release. Within seconds, a gush hit the back of my throat as his hands grabbed the back of my head to bury himself as deep as he could. In the seconds after he came, he released my head and pulled himself out of my mouth. His cum dripped from my mouth, down my chin onto my chest. Looking up at him, he smiled down at me.

He leaned down and pulled me softly up from my knees. Pushing me back towards the pole he had hung my dress on. I felt the cold metal hit my back and as the cold spread through my body, my nipples became hard. He fumbled with his belt, slipping it out of the loops and took off his pants. He grabbed my wrists lightly and told me to put them above my head. I did not hesitate. He wrapped his belt around them and tightened them to the pole, leaving me tethered. My chest began to rise and fall faster with excitement. His hands wandered on my body, starting by caressing my face and neck. He felt every inch of my skin without touching my breasts or pussy. Lightly he traced my arms, the length of my legs to my ass, my hips to my ribs. It was sensual and light, and it surprised me. As I settled in the rhythm of his touch, I closed my eyes and began to relax my breathing. Within seconds of my mind wandering, I jolted my eyes open as he grabbed my breast hard. "I want you to watch all of this Brooke. You are here with me, not off with someone else in your mind." I opened my mouth to tell him that wasn't what happened, but he captured it with his. Kissing me deeply, my protest was silenced.

My breathing went back to heavy as I enjoyed our styles meshing and the heat that was spreading throughout my body. Suddenly, my nipples were being tweaked and pulled and my eyes were open again. After this, I came back to reality, realizing I was on a suburban playground, almost naked, tied to a pole, exposed. A slight panic came into my head as I scanned the playground. I felt his mouth encompass my breast as his hand cupped it and his other made its way to my ass. I realized that the probability of someone being on a playground this time of night was extremely low, but it still sat in the back of my head. I began to let go of the thought as Scott was beginning to make my body beg for more.

His tongue flicked my nipple and he tried to get all of my breast in his hand. Grabbing roughly at both of them, I found myself arching my back. I couldn't hold back from moaning. My pussy was starting to drip from the wetness, and it began to show on my panties. I was aching to be touched. Scott looked down as I was arching, and saw the glistening on my shiny underwear. He dropped down to have his face level with my pussy. I didn't know if it would be his tongue, fingers or dick, but something had to make a connection and soon. He slid my panties off slowly as I rocked my hips to help him. When it got towards my shoes, I turned my ankles towards him for him to take them off. He looked up at me and said no. "Those are staying on. Use the belt strap and pull your legs up." I obeyed and as my legs came up he slipped the panties off. I dropped my legs back down to the ground and separated my stance. He rubbed his hands on my inner thighs, and up to my belly button and back down to the top of my pelvic bone. Previously, I had only had a landing strip for pubic hair but for our meeting, he asked me to grow my hair out and have it professionally trimmed and shaped. He wanted me "to look like a woman." I obeyed.

I was trembling, not knowing if it was the crispness of being naked, or the anticipation of what was to come, it was incredibly overwhelming. His hand began to slowly retreat to the mound of hair, crafted to his specifications. He took his index finger and slid it down my slit, making me moan out loud. He then took his middle finger and inserted it deep inside of me. "My my, how wet we already are. I've only just begun." The index finger joined the middle finger and his thumb went to work on my clit. He separated my legs further and drove his hand deeper into the wetness. I found myself riding on his hand, pressing hard against his thumb. When I thought I couldn't take anymore, I felt his tongue begin to lick my pussy lips. He separated my legs even farther and flipped himself around so he was facing the same way as I. The way he had separated my legs, I was basically sitting on his face. I did my best to bring my legs closer together, but he used the aid of the belt holding my wrists and used his arms to hold my thighs up and across.

Spread eagle couldn't begin to explain how open I was if someone were to be watching. He darted his tongue in and out of my hole, lapping up my juices. I had no choice but to let go and enjoy the ride. His tongue did things to my pussy that I had only dreamt about. My body began to buck against his face, and my moans got louder and louder. He let down one leg and used the hand to begin to finger me again as his tongue traced and tickled my clit. I couldn't help but ride up and down on his hand, my body was in control now. Grinding against anything that he had near or in me, I got to the brink and came hard. My hands clenched in fists, my chest heaving and my legs shaking I opened my eyes. Scott was getting up, smirking and wiping my cum off of his face. He moved towards me, leaning in close to me and loosened the belt to allow my hands free. My wrists were sore, but my body was in such a state of content, I didn't notice.

I turned around and went to grab my bra when Scott grabbed me by the arm. "What are you doing?" he asked me. "Getting dressed? Is that bad? I figured we both came, so we were done," I replied. He laughed. "Absolutely not." As I looked at him, panic spread throughout my body. Behind him, I saw movement coming towards us. "Oh my God Scott... someone's coming!" I hissed. "Yes, you already came," he retorted. Annoyed, I flipped him around to look at the figure making its way closer. His body didn't tense the way mine did, instead, it stayed loose and relaxed. He grabbed my bra out of my hand and threw it back on the pole. I stood frozen, completely humiliated. As the figure got near us, I saw it was a man, Scott's age. He wasn't in a police uniform, so a slight bit of panic left my mind.

"How'd she do?" he asked Scott. My head whipped around to Scott. "What the fuck is going on?" I yelled at Scott. He came towards me and grabbed me under my elbow lightly. The movement exposed my breasts I was desperately trying to cover from the stranger. "I thought I told you to trust me?" he questioned. Before I could retort, he looked me in the eye. "Brooke, I realize that you are naïve and innocent, but, this will only do you good. I know you and wouldn't encourage something that I didn't think you really wanted." A flush came across my face, knowing that I had talked to him about a threesome with two men. "I'm going to ease you into things, I promise. You will enjoy everything we will be doing, and if not, just say the word, and we will be done. If you want though, Jim and I will make you feel unbelievable."

I couldn't get myself to protest. In the end the thought of two men with their hands all over me was more appealing then being seen as a nice girl or the fear of getting caught. Scott had made me cum harder then I had ever done before, and that wasn't even from being fucked. I couldn't cheat myself out of the chance of another orgasm like that.

He knew my silence meant compliance and guided me over to the plastic picnic table off to the side of the playground. The park light shined directly down on the table. He laid me on the table, bringing my ass close to the edge. Jim stood off to the side, standing still. Both Scott and I were still naked from our previous exercises. Scott spread my legs wide, exposing my sex. I blushed knowing Jim could see it. I turned my head away wondering what I had gotten myself into. I felt Scott's hand on my face, turning it towards him. "You are not to take your eyes off of Jim, do you understand me?" I nodded in agreement and he turned my head back to Jim.

Moving back down my body, Scott began to tease my already sensitive pussy. My eyes rolled back into my head and I had to fight to bring them back to Jim. I focused in on his eyes as Scott continued to make me wetter and wetter. As his fingers explored my cunt I heard "you won't believe how tight she is Jim- she knows how to use it too." I watched as Jim's pants began to get tighter. I wondered if his cock was like Scott's. Scott continued to work on my pussy, pushing his hands up my legs making them stick up in the air. Jim's view was a tanned, naked body with legs stretched in the air, wedges still on with a man in between those legs, making her moan. The thought of his view caused me to arch my back and grab my breasts with force. I tweaked my nipples, enjoying the feeling of his tongue manipulating my clit and pussy. I focused in on Jim, the thought of him watching me spurred me on now. I wanted him to know that Scott was pleasing me and I enjoyed it. I wanted him to imagine it was him eating me, I wanted him to desire me. Scott was getting me close and my body began to prepare for another orgasm. I grabbed his hair and drove his tongue hard on my pussy and moaned loudly as the wave came over me. I kept my eyes on Jim (when I could keep them open) as I came. I closed my eyes softly in content as I finished.

As I drifted in and out of a light sleep I saw Jim removing his shirt and unbuttoning his pants. I felt Scott's hand on my pussy, capturing some of my juices. I looked at Scott and saw him spreading my cum on his erect cock. His head glistened with his hard work. My pussy was tired, but tingled with the thought of him inside of me. He looked up and I quickly reverted my eyes to Jim as I had been told. Jim was now naked with his hand on his cock. It didn't look as big as Scott's, but it was by no means small. My pussy wouldn't say no to a dance with his dick. As I began to dream about Jim's cock, I felt Scott's head enter me. I threw my head back with pleasure. He entered me slowly, but persistently. He did not allow my pussy walls to compensate by pulling out and going back in. He drove himself in slowly, my mind thinking there was no way there could be more. I heard him grunt and the sound caused me to clamp down on his cock with my pussy. He whispered for me to relax or he'd never fit. I took a deep breath and released allowing for him to penetrate me further. My legs hung off of the table, spread wide as he was standing at the end, sliding himself in. I could have came again, right then. I returned my gaze to Jim who had come closer now.

Scott finally had himself fully inside of me, and slowly pulled himself back out. He repeated the full entry again, this time moving faster. Again, he pulled himself out and then pushed himself back in. I felt his hands on my thighs pulling me closer to him. My breasts began to move back and forth with every thrust, bouncing as he drove into me. I lost any control I had, moaning loudly, telling him to never stop fucking me. Lost in the moment, I didn't realize Jim had come next to me until I felt his hand on my nipple. He was tweaking it as he moved his other hand up and down his shaft. I looked up at him and grabbed his balls lightly. As Scott fucked me, I gently rubbed on Jim's sack. Jim smiled and grabbed my breast. After a minute, I opened my mouth wide and guided Jim's cock into my mouth. I kept it open and used my tongue to tease his dick as the rigorous bouncing I was experiencing could be dangerous if I were to clamp down. Jim didn't seem to mind as I paid attention to both his cock and balls. The moans I let out created a whole new sensation on his cock.

My body was bucking with pleasure, I knew I was close and Scott picked up on it too. He began pumping me faster, lifting up my ass to drive in deeper. As I started to call out, he used his thumb to put pressure on my clit, causing me to loose all control. Jim's cock fell out of my mouth as I came loudly. Scott continued to pump himself in me, enjoying my pussy coming on his cock. As my pussy walls closed in on him, I felt his cock begin to bulge and knew he was close. He drove it in deep and hard and I heard him grunting and pull out quickly. I felt the wet heat hit my breasts and neck as he finished.

I felt my hand fall away from Jim's cock as I was in a state of orgasm. Close to unconscious, a small smile spread across my face. I felt my legs being closed and my hips being moved. I struggled to come to as I was being turned over on my stomach and legs dropping to the ground. I looked to find Jim, but Scott came into my view. I saw his soft cock in front of the table, and felt hands on my hips. I was lightly pushed to the side of the table, my knees being placed on the seats, but farther then shoulder width apart. I put my elbows up on the table and leaned forward, assuming a doggie style type position. My world became less hazy as I came down from my orgasm. It was Jim's turn.

He reached down and used my own juices on his cock as Scott had done. He aggressively began to rub my pussy and clit from behind me. He used his other hand to smear Scott's cum all over my breasts, rubbing and cupping them roughly. I began to moan with pleasure, excited by the idea I was going to experience a new cock. Jim knew when I was ready and began to insert himself inside of me from behind. As he did, Scott positioned himself on the other side of the table. I was able to give him proper head as he laid out across the table. My mouth fell right on top of his drained cock that was covered in my own juices. Again, I was tasked with getting him hard in my mouth.

Jim began to drill himself into me, and I felt every inch of him. As he got a rhythm going I began to move my hips to it while I sucked on Scott. Moans escaping my mouth, overcome by the feeling of two cocks at once. Jim slapped my ass hard, making me yell out for him to fuck me harder. It caused him to drive harder and deliver another slap to my red ass. Unable to concentrate, I pulled my mouth away from Scott's cock and gasped for air as my pussy was drilled. Jim reached down and grabbed a handful of my hair and pulled hard. Scott stood up and put himself back in my mouth. I gagged and gargled, and he enjoyed it all. Grabbing at my chest he pumped into my mouth in the same rhythm that Jim pumped into my cunt. I wrapped my arms around Scott's ass, pulling his cock deep into my throat. Jim gripped my hips tightly, pulling me close to him as he could get me. One hand traveled down between my legs as he pushed deeply into me and tweaked and played with my dripping clit. I knew I couldn't take anymore and let the feeling overtake me. Screaming, I came hard on his cock. In turn, Scott pumped my face harder with his cock. Jim pulled out and looked at Scott. Scott pulled out of my mouth. Jim got up on the table and laid back. Scott guided me on top of Jim, facing away from Jim. I slid down his cock, dripping. I began to bounce on his cock, quickly at first. I could hear him breathing hard, getting close. I decided to slow him down. I lifted myself up slowly, and drove myself down even more slowly. I repeated this action over and over until he grabbed my hips and started moving me up and down to the rhythm he desired. Knowing I had tried to control his orgasm, he decided to get revenge. He drove my hips back and forth on his cock, instead of up and down. He moved me just enough that I could feel his cock hit my gspot, but not enough to make me cum. He started to drive my hips faster, and when he knew I was building, he started moving my hips up and down.