Jennistoy's Stories
Ben's First Time by Jennistoy
Ben's First Time
The following story is for readers of legal age or readers who have interests which lie in the direction of BDSM. If you have comments or suggestions, feel free to E-mail me at Jennistoy@hotmail.com. I do try to answer any and all that I get. You can also find me on line under Jennistoy for Instant Message, (I will not accept an IM if you do not have a profile), or you may check out my website at http://home.talkcity.com/BoomerSt/jennistoy/index.html.
It was the typical college bar, lots of young faces flushed from a combination of heat, hormones and alcohol. I shook my head while I was sitting at the bar drinking a beer. I was too damn old to be in here. I didn't get any strange looks when I came in, but I had felt way too soul old, if not actual physical years.
I had dressed accordingly for a Friday night; I was in a short, light silk, spaghetti strap dress. Spike heels adorned my feet and gold glinted around my right ankle. The dress was a copper color; my fingernails and toenails were in dark red. My make up was not heavy; it was actually light enough so it appeared that I wasn't wearing any. Several gold rings glinted on my fingers and a fine gold mesh choker went around my neck.
I went back to reading my book, knowing that I stood out in the loud bar, but also knowing that Ben would know me right away. I had become absorbed into the story when I was bumped rather hard from behind. Immediately a form shot around from beside me and I found myself looking into Ben's face. He was angry at whoever had run into me, but a restraining hand on his arm settled him right down. He bowed low over my hand brushing his lips against the back of it, charming me almost instantly.
"Jenn, I am so sorry, I should have never met you here." His softly accented voice rolled over my skin. I waved it off and ran my finger over his jaw line. Leaning in, I laid a kiss there and whispered,
"Dance with me." Ben's eyes widened and he smiled as he slipped his arm around my waist. We strolled over to the pitiful square they called a dance floor and he bent his head to allow me to wrap my hands behind his neck. I started rubbing his neck while we slow danced to the metal and rap music that blared from the speakers hidden in the walls. I made sure that my body rubbed up against his and smiled in satisfaction at his body's response. Ben was slowly kissing and biting his way around my neck and I let him get to know my taste.
"Mmmm, I like you hard," I said. Ben's eyes darkened and I could feel the flush run through me. My nipples hardened and I knew I was wet. I smiled and ran the back of my hand down his chest and his stomach. I didn't stop there, but let it slowly drift down his groin, lightly caressing him through the jeans that he wore. Ben sucked in his breath and lightly touched my face.
"Ben, let's go. I want to have you naked and to myself. Somehow I don't think the management of the bar would appreciate you stripping down here." He chuckled and shook his head. On the drive back to my hotel, I stopped at a grocery store and picked up some dinner. There was enough for the both of us, but I intended to make sure he got his in slow bites. The fruit, chicken and chocolate whipped dessert were all packaged up and we started off once again.
Once we got to the hotel, I laid out the food. Ben had followed me around the store, not questioning, just watching and holding items I handed him. He smiled when he saw the two bottles of wine I had picked up earlier and opened one, pouring each of us a glass. I touched my glass to his and we sipped, not saying anything, just staring at each other. I slowly took the wine from his hand and started to strip him. He allowed himself to be undressed and I took my time discovering him as I bared his skin. Lightly I traced my fingers over his pecks, and he moaned when I lightly pinched and twisted his nipples. His skin jumped when I ran my hands over his stomach, I did so enjoy the feel of the muscles under my hand.
I knew at that moment it didn't matter that Ben would never have looked at me twice had we met on the street. I was much older than he was, (9 years) and much less in shape than the women he normally dated. Ben and I had met on line and the relationship had continued over time. He had contacted me while he was still in college, and we had stayed in contact through out his Jr. and Sr. year. It had been 2 years we had talking and feeding the fire for this night. Ben had a love for pain and I had a love for giving it. We were a good match for the night. I wanted to torture him for a few hours. I wanted to use his body. He knew all of this and he wanted me to do that too. I opened a drawer of the dresser and pulled out two nipple clamps that were attached together with a silver chain. Ben's eyes widened and he shivered as I clamped down each one.
I bent my head and licked the tips of the nipples that peaked through the clamps and Ben's hands gripped my shoulders as he swayed. Leaning up, I slowly kissed him while undoing his jeans. Our tongues caressed each other and his hands tightened as I slipped off first his jeans then his boxers. His cock stood hard between us, it's tip lightly brushing against my dress.
Breaking the kiss, I stepped back to examine his cock and balls. I rolled his balls in between my fingers, getting a feel for their weight and resiliency, then I gently tugged on his scrotum and smiled when he moaned my name. I caressed the tip of his cock and watched him jump slightly at the contact. Very slowly I pinched the tip of his cock and watched him arch forward into my hand. Ben's hands were gripping my shoulders with enough force to bruise me but I have to admit to not caring. Slowly I slid my hand down his cock and separated his balls into two separate sections. One ball I popped through my fingers and started to pop it back and forth. Ben's head was thrown back and his eyes were closed. His breathing was a bit unsteady and his hands flexed convulsively on my shoulders. I stepped back some more and walked around him, trailing my hand over his waist while inspecting his body. He groaned softly and I could feel his weight shifting as he waited for my perusal. I ran my hand down his ass, lightly teasing him. Slowly and lightly I caressed his thigh and slipped my hand in between his legs.
I pulled his balls back toward his ass and he moaned softly at the tug. I chuckled and ran my index finger over his tight asshole. I intended to use him there tonight, but I did have all night long in which to indulge myself. Ben moaned and seemed to tighten up more. His hands flexed at his sides and he shuddered all over. So far I had not done much to him, but he was beginning to realize that I was in no mood to rush it. From behind him, I slid my hands around his waist to his stomach, slipped my leg between his two and said softly,
"Spread your legs darlin', I want those balls hanging free."
"Yes Ma'am," he whispered harshly. He spread his legs and I tapped at him again.
"Wider!" He struggled to obey and then chuckled softly and said,
"I can't I'll fall over." I slipped my hand around his ass, between his legs, gripped his balls and pulled back quickly.
"I said, wider." Ben yelped and managed to stretch his legs a few more inches. I chuckled and stroked his back, "Good." Ben was shaking and he appeared caught off guard by the sudden action. I leaned forward and nipped at his shoulder. I hadn't let go of his balls, just relaxed my grip a bit. I noticed that Ben had started to sweat.
"Nervous darlin'?"
"Yea, I am." I smiled at his admission and savored the sound of his voice. I knew his voice intimately and knew how he sounded at every phase of a session. Right now I knew that if I bothered to look at his cock, he would be oozing pre-cum. I kept a grip on his balls with my right hand and with my left ran two fingers over his tip. When they were coated, I raised one to my lips and licked it clean. Ben groaned. The second I raised to his and he eagerly sucked my finger clean. His eyes locked with mine, the desire I saw there made me smile. I tightened my grip on his balls and watched him flinch as I dug my nails in a bit.
"Oh God," he moaned. I chucked and nipped at his bicep. I released his body and walked over to the dresser. There was a black bag sitting unzipped on the top of it. Ben's body sagged and he watched as I pulled out a length of white cotton clothesline. I held it out to his lips and watched as he kissed my fingers and the line while they were tangled together. His cock jumped at the thought of what was going to happen. I tossed the clothesline on the bed and reached in the bag again. From it's depths I pulled a leather cock ring, a bag of black clips, four pairs of handcuffs, a long silver chain, a riding crop and a pump action buttplug. Ben's eyes followed each item out of the bag onto the bed where I tossed them. I also pulled out a bottle of lube and reached behind the dresser to pull out two extension bars. I could see his pulse speeding up in his throat and he gulped hard.
"Are you sure you want to do this?" He closed his eyes and licked his lips.
"God, yes!" His voice cracked a bit as he went on. "I want this more than ever before." I nodded and reached to the bed and pulled the clothesline off. I walked behind him and quickly tied off his balls. They were both pulled together and I wrapped the clothesline down his scrotum until it reached right above his balls. I tied them off again and tugged experimentally. Ben groaned. I chuckled and said, "I do love hearing that sound. I am going to like your tears even more."
Ben flinched and said, "You think you can make me cry?"
I laughed and pinched one ball hard with my nails. "I know I can."
He nodded and sucked in his breath at the pinch.
"Maybe," he said behind clenched teeth.
I laughed and leaned next to his ear, "I can make you cry from wanting to come, and I can make you cry from the pain in your balls. It will be a tossup as to which I do." Ben closed his eyes while a shudder ran over his body. I gently pushed him to his knees and clipped a pair of handcuffs to each ankle and wrist. To the ones on his feet I attached a spreader bar, ran the left over rope through one end of the cuffs, making sure he was trussed up tight. His balls were pulled back away from his body and towards his backside. If he moved at all, he would be pulling on them. I snagged the crop and laid a few quick hits to his balls. Ben flinched. I smiled.
I sat down on a chair and had him come towards me on his knees. He flinched as he moved, the cord doing it job and pulling on his balls each time he moved a leg. When he arrived next to the chair, I pulled a few clips from the bottom of the bag and clipped them to the tip of his cock. Ben swayed and he whimpered. I leaned forward and kissed him as I slowly pulled the clips off of his tip. His gasps were poured into me through is mouth. I noticed him softening up and flicked at his tip as I taunted him.
"What's the matter Ben, hurt a little too much to keep you hard?" I ran a finger up from his navel to his throat flicking at his Adams apple. "You wouldn't want to disappoint me would you?"
Ben's eyes locked with mine and he flinched and said, "No, but I can't help it. It's not fair! I've..."
I cut him of swiftly. "I never said I would be fair, I did say that we'd do what we had always wanted to do." I stroked him slowly; my eyes never left his. "Get it up Ben or you'll be in hell much sooner than I had thought."
His eyes flashed at me and I could see his temper flaring up. "What makes you think you can treat me this way?"
"You asked me to."
He fell silent and I sat down and tugged on the silver chain that hung between his clamped nipples. Ben whimpered and he closed his eyes to savor the sensation. I smiled and noted that he was hard again and I softly ran my hand over him. I reached for the crop and laid 5 lightening quick lashes to his tip and Ben cried out. I leaned over and popped a piece of the chicken into his mouth. He chewed it slowly, watching my face. I laid the next piece in my hand and made him dip his head to take the chicken from my palm. Every time I had him eat from me, I made him stretch out a bit and pull his own balls. The final piece was placed between my lips and when he leaned forward I leaned back until he whimpered. I bit through the meat as he finally closed his mouth around it, allowing him to have it.
I smiled and got a fork and started in on the chocolate whipped thing. At first Ben hesitated, I knew it was because he was fitness buff, but he couldn't resist the sweet taste of the silky desert. I loosened the rope and allowed him to stand. Once he was standing I bent him over the chair. Once he was there I secured his hands and feet. He couldn't move much when I was done with him.
"Ah look that that ass," I whispered to myself as much as to him. Ben flinched but didn't shy away. I ran my hand over it teasing him. I had picked up the crop and lashed him with it several times. Ben clenched his teeth, but didn't cry out. I added 10 more just to see his reaction. He gasped, but no tears came. I then took the butt plug and lubed it up. Ben could see what I was doing and he gulped. I leaned over and slipped it between his buttocks. I knew that Ben had not had anything much thicker than a finger in his ass and this plug was 1.5" across at it's thinnest. When blown up it would go to almost 4.
I leaned toward him and held the plug in front of his nose.
"I'm going to put this up your ass and you will wear it until I decide to fuck you with the strap on I brought with me." Ben closed his eyes and shuddered. I reached over and yanked the nipple clips off, which caused him to cry out. I slowly started working the plug into him. He didn't fight it, but instead pushed against it. As it slipped in he closed his eyes. I pumped it up about 1/2 way and untied him. He stood at my command and I handed him his clothes. He looked at them while I reached for the keys to the cuffs. I uncuffed him and told him to get dressed. When he was done I made a phone call and smiled as I reached into the black bag again. He watched as I brought out a collar and leash both that were both made of cold metal. I locked him into the collar and clipped the leash on his neck.
"Where are we going?"
"We're going to meet some friends of mine, you are to please the both of them. Do you understand?"
Ben went gray, then blushed to the roots of his hair. He had expressed a desire to be with another man, while being taken by a woman. I was going to put him to the test tonight. He swallowed visibly and nodded. I reached up, stroked his cheek and told him I would be very proud of him if he could do what I wanted him to. His breath shuddered out. I took his hand and guided it between my legs. My panties were soaking wet and he groaned. I allowed him to slip a finger inside me and feel the wet heat that I was emanating. I chuckled and told him if he was a good boy and did me proud I would let him have some of that. He nodded emphatically and we were off.
I had been given explicit instructions telling me how to get to the private party. We arrived and were met by a young man at the door who looked me over, then looked over Ben. He took my name, opened the door and we were let into the home. Before we entered the main room, I instructed Ben to strip. He did so in the hallway and we put his clothes into the closet. I clipped his nipples again and added the cock ring. Ben looked at me with fear in his eyes. I stroked his face and we entered the room. There were probably 20 couples in the rooms, some people were naked and in acts, others were just talking with each other.
Scott and Lori greeted me and I was subject to several hugs and kisses before introducing Ben to them both. I had known them for many years and had many times when I hated to leave their arms and go home. Both were submissives with me, and both were bi-sexual. Lori walked around Ben and looked up at me with a small smile
"Jenn, he's beautiful!" I nodded and agreed with her and Scott stood before Ben and placed his hand on Ben's chest. He looked him up and down and turned to me.
"He's not hard, is he scared?"
"Hmm, I dunno Scott, ask him your self, he has a tongue."
Scott turned back to Ben and repeated his question. Ben nodded slowly and looked at Scott. I smiled at the both of them and we left the main part of the party and went into Scott's study. I sat down in a chair and Ben dropped to his knees next to me. Scott called him over and pulled his wife's dress up.
"Look at that pussy Ben, she's been horny and playing with herself all evening. Eat her out Ben."
Ben shot a look over his shoulder at me and I nodded. Ben didn't need too much coaxing to attack Lori's dripping pussy. While he was doing that, Scott had come over and was working his way up my inner legs to my pussy. I moaned a bit which caused Ben to stop and watch with a jealous look in his eye. I motioned for him to come over and he left Lori and basically shoved Scott out of the way. Scott shrugged and he lay on his back under Ben. Lori crouched over Scott and began to ride him while Scott licked and sucked at Ben's cock. I wasn't sure Ben was aware of who was giving him the blowjob, but he was enjoying it. I cautioned Scott not to let him cum. Ben raised his eyes up to mine and whispered, "Jenn, please, let me come."
I shook my head and told him that when he finally came tonight, it would be inside me and he would be cleaning his cum out of my pussy. Ben shuddered and slowly pulled away from Scott. I told Lori to go sit on her husband's face. She moved eagerly and settled herself over his lips and tongue.
"Suck him off Ben."
Ben looked miserable, but I slowly ran a finger up the inside of my own pussy and tasted myself. Ben shuddered and went to work on Scott. Soon he had Scott writhing and moaning against his wife's sloppy pussy. I had slipped onto the floor and was stroking Ben's cock. I flicked at his balls and moved the plug for him as well. He had stayed hard especially with me whispering how he looked and how much I loved watching him play the bitch for me. Scott finally came and Ben rolled off of him and onto his back. Lori bent over him, taking his cock into her mouth. I pulled her off, stood Ben up and left the two of them in the study. We went to the front door, where Ben threw on his clothes and we went back to the hotel. I had him strip and I went in and took a bath with him there to scrub my back.
When I was finished I stood and had him dry me. Ben was rock hard and his hands were shaking. I noted the dark circles under his eyes and checked the clock. It was two in the morning. We had met at the bar at 8. I led him to the bed, laid him on his stomach and slowly slipped the plug out. I had him go to the bag and get the dildo and strap on. I had him put it on me and then had him suck the dildo. I turned him around, lubed the dildo and his ass, slipping two fingers inside him and then slowly began to fuck him. I went slowly until he started to back up against me. He started talking,
"Jenn, please, I am going to come. Please stop, I want to come when you tell me to, not now!"
I listened to him and pulled out. He sagged against the bed and sucked in great breaths of air while I took off the harness. I had him roll back over on his back and I loaded clips on his balls. There were 15 in all. Ben was breathing rapidly and I looped the thin silver chain through the clips and began to slowly pull them off. I didn't let up and soon I had Ben sobbing from the pain. I had broken him.
"Ben, do you want to fuck me? Do you want to bury your cock deep inside me?"
Ben nodded helplessly and I stroked his face. I mounted him and slowly started to ride him. Ben gripped my hips and started to fuck at me. I cried out as I came and vaguely heard him begging me to let him cum. I looked into his eyes and told him to cum with me. He exploded inside me and cried out my name. I dismounted him and had him clean my pussy. He cleaned our cum out of me and fell back against the bed. I smiled and patted the pillow next to me.
Ben lay down but didn't seem inclined to sleep. He lay on his side, playing with my nipples but soon his eyelids began to drop. I watched him sleeping and wished that I could take him home with me. I would love to send him off to work with a pager so I could control what he did during the day and then have him to play with all night. Ah well, such was life. I snuggled down in the blankets and drifted off myself.
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