PUBLISHED BY:
Maggie Chatterley
SMASHWORDS EDITION
Cherry
Copyright © 2012 by Maggie Chatterley
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Cherry
I was still a virgin when I graduated from high school in the 1970’s. In high school, I never dated boys and the only sexual experience I had was with my best friend, Amy. When I left for college one of the first things I wanted to do was get my cherry popped. I was attending college across state, and going alone, without any of my high school pals. The school I was planning to attend was the only one offering me a scholarship. It was located in a quaint, but small college town.
As I drove into town that first day, I noticed a large impressive Victorian house off the main street. I had no idea that it would be where I would lose my virginity - or more accurately, where I would sell it. Had I known virginity was such a valuable commodity to some, I would have held out for a higher price. Yet, in retrospect, I have no regrets.
I moved into a college apartment. The apartment complex was part of the campus, and they assigned roommates. Susan was a freshman, and Jill a sophomore. Susan was a chatty little redhead, whose boyfriend also attended our school, while Jill was single and appeared to be quite studious. I often wonder how different my first time would have been with a man, had I never met Susan and Jill.
During my first week at college, I visited a free clinic, had my first gynecological exam and got a prescription for birth control pills. Susan noticed them in our bathroom one night and said, “I didn’t know you had a boyfriend.”
I told her I didn’t, which then led to our conversation about sex and my desire to lose my virginity, so I could get past the pain and mess, and start exploring. Instead of being shocked, Susan blurted out, “Well hell, if you are still a virgin, don’t give it away. Sell your first time. If I was still a virgin and didn’t have a boyfriend, that’s what I would do.”
I imagine I looked shocked. Suddenly, I had an image of me standing on some street corner, selling my virginity to an overweight middle-aged man, who smelled like stale perspiration and had a receding hairline. It was as if Susan read my mind. She chuckled and then took me by the hand and led me into Jill’s room, and closed the door behind us. Jill was sitting at her desk doing homework. She looked up when we walked in.
“She is a virgin.” Susan blurted out. Jill smiled, as if she and Susan shared some secret, and then Jill closed her schoolbook, giving us her complete attention. I felt incredibly foolish.
“Does she want to lose her virginity?” Jill asked quietly, directing the question to Susan instead of me. Susan nodded, as if to say yes. Jill then asked if I had a boyfriend, to which Susan told her no. This pleased Jill, who looked at me a bit as the cat does before he pounces on his prize.
“Angie,” Jill began, “what I am about to offer you must remain our secret. If you don’t want to do it, fine, but you must promise never to share what I tell you with anyone outside of this room. Do you agree?” Jill was a tiny thing, barely 5’ 3”, slender with straight and silky dark hair that fell to her shoulders. She had piercing green eyes, a heart shaped face, and while she might appear like a harmless little thing upon first meeting, at that particular moment I knew I would never cross Jill. I was also curious as hell, so I didn’t hesitate in making the promise, in spite of its possible outcome.
Jill went onto explain there was a wealthy man in town, who had a sexual preference for virgins. He was willing to pay a young woman a thousand dollars for the privilege of being the first. As for me, the money sounded good. I was planning to get a part time job; my scholarship didn’t cover all my expenses. Yet, I really didn’t want sex with some ugly stranger.
“Don’t get me wrong, he isn’t into children, he simply likes virgins, and he can afford to pay for his fetish. In fact, he will demand you show your driver’s license, to prove you are over eighteen.”
“But what does he look like?” That was the first thing I blurted out, after agreeing to keep Jill’s confidence.
“Ohh…..” Jill began slowly, “he is good looking, I mean, really good looking. An older man, I think about 35 years old, with dark hair and dark eyes and over 6 feet tall.” Jill looked a bit starry eyed as she spoke.
“Did you…” I whispered.
“Yes, he was my first. If I had it to do over, and he didn’t pay, I would still let him be my first. The truth is…” Jill didn’t finish her sentence, but I understood. She would have eagerly entered into a long-term affair with the man, but sadly, after the first night, he was no longer interested. Jill, rejected by the object of her affection, compensated by supplying fresh virgins, and hoping secretly that someday he would reward her efforts with another night. I was the next sacrificial lamb, and Jill attentively prepared me for slaughter.
The following week I found myself alone, standing on the front porch of Robert Mason’s Victorian house. To say I was nervous would be an extreme understatement. I realized I had not yet met the man who I was planning to give…I mean sell…my virginity too. Another prevalent thought running through my head at the time was the fact that I was 18 years old, and had never kissed a boy, much less a man. Oh, I kissed little Billy Clark behind the bleachers when I was in the fifth grade, yet that hardly counts.
Before I left my apartment, I had taken a long, hot shower. I soaped up every nook and cranny of my body, until my skin bore the light scent of lavender. Jill had taken me shopping several days earlier, and with her, I purchased a new pair of lacy silk panties and a matching bra. They were light pink.
I normally went braless, but Jill insisted I wear sexy undergarments beneath the cotton shift I intended to wear for my encounter with Mr. Mason. On my feet, I wore a pair of strappy white sandals, and my toes sported a fresh pedicure. I was all in pink, from my toenails, to my undergarments and even my cotton sundress.
Initially I complained about the expense, but Jill reminded me of the money I would be bringing home. Ironically, I now had to go through with the arrangement, as I’d spent my grocery money on underwear and a pedicure.
At the time, I didn’t realize how young I looked. Innocent and virginal, a soft pink offering; femininely attired in an era where my contemporaries normally wore frayed bell-bottom jeans and bright colored halter-tops. My auburn hair, which is naturally curly, was tied back in a pink bow. It fell to the center of my back in glistening curls.
When Robert Mason first opened the door, I was stunned at his good looks. Jill hadn’t exaggerated. I supposed her estimation of his age was correct, and at the time thirty-five seemed like such an advanced age. Today, it seems very young. He reminded me of one of those tall, dark playboys from a Rock Hudson or Frank Sinatra movie. Yet, much better looking than Sinatra.
Mr. Mason’s initial expression wasn’t especially welcoming. In fact, he looked annoyed and rather than ushering me into his home, he immediately demanded to see my identification. I understand now; he felt I was much younger than my years. I nervously handed him my driver’s license, after fishing it hastily from my purse. He didn’t say anything right away, instead he just stood there in the doorway, me on the front porch, and him holding the driver’s license in his hand, glancing from it to me, and back again.
He finally mumbled something about me being exquisite looking, as if he still worried I looked too young, but considering my ID and my appearance, he wasn’t going to send me packing. He handed me back my ID, and I returned it to my purse.
Rather than asking me to come in, he opened the door and stood to one side, as I quietly walked into his home he closed the door behind me. I found myself standing alone in the home of Robert Mason, who I later learned, was one of the wealthiest men in the state. I’ve often wondered how much Mason would have paid me, had I asked for more. But, I didn’t.
“Let me explain the arrangement,” he began. There was still no hello, no ‘hi my name is Robert, call me Bob,’ instead, he, in his no- nonsense way proceeded to lay out the terms of our business arrangement.
“In a few minutes I will go upstairs to my bedroom, which is the second door to the right, after you go up the stairs. Before you join me, I expect you to read and sign this contract,” which he then handed me, “and if you agree to the terms, ring this bell and wait here. If you do not agree to the terms, turn, and walk out the door. But, understand, once you come through my bedroom door, there is no turning back. You will remain with me until no later than 8 am. I may send you away sooner.”
“And if I wish to leave sooner?” I whispered the question, surprised I had the courage to ask, for I confess, the man frightened me.
“You can’t. You won’t be allowed to leave, or to refuse me in any way. When you sign that contract, you are giving me permission to use your body in any way I desire.”
At this point, my eyes widened in fear. A smart girl would have turned and raced from the house, without looking back. Yet, I have not always made the wisest choices, and this was no exception. If anything, I found myself virtually bolted to the floor, unable to move away and flee.
“Don’t worry,” he went on, “while I will be honest with you, some of it will hurt, but what I have planned for you will not leave scars or cause permanent damage, other than the loss of your virginity.”
“But…what if when….when you start…if I want to stop?” I whispered my question, compelled to ask.
“I won’t stop. And if necessary, I’ll tie you to my bed and finish with you.” He actually smiled when he said this, as if the thought of me resisting excited him. I suddenly remembered what my friend Amy had told me about her first time, and how her boyfriend had initially stopped, because it was so painful. I realized that unlike Amy, once I entered his room I would not have such a reprieve. I felt like that preverbal moth drawn to the flame, heading for destruction yet unable to resist.
He had nothing else to say, other than a command to read every word contained in the contract, which I did. He turned from me and walked up the stairs, and out of my sight. I was surprised to discover the document was quite lengthy and detailed. One section expressly stated that if he discovered I was not a virgin, he would not pay me. The document was in effect a non-disclosure statement, a signed contract stating I agreed to not discuss our transaction, nor bring any legal charges against him, should I later regret our bargain. In retrospect, I wonder how binding such a document was, yet, I was young and he intimidated me. I often wondered what would have happened had I ran from the house, taking the unsigned contract with me and shared it with the local newspaper. Of course, I would never have done that. I was too curious to see what waited for me in Mr. Mason’s bedroom.
I rang the small bell, which sat on the cherry wood side table in the entry hall. Suddenly a man I had never met appeared. By his clothes, I assumed he was Mr. Mason’s butler, and I wondered if he had been standing in the shadows the entire time.
He was a serious looking fellow, much older than Mr. Mason, and he wore round, wire rimmed glasses.
“I assume, Miss, you intend to sign the contract. If so, I will be your witness,” he handed me an ink pen and spoke in a low tone, and I could tell he had done this many times before. He didn’t seem embarrassed or uneasy, more like a servant tending to a routine duty he had done many times before, and would do again, long after I was gone.
I was so nervous I could feel a tremor in my right hand, and I had to concentrate on what I was doing, or else my signature would be unrecognizable. After signing the contract, he also signed the document, as the witness. I stood there, a bit overwhelmed, when he nodded goodbye, and then left the house, contract in hand, shutting the door behind him and leaving me in the house, alone, with Mr. Mason.
For a very brief moment, I contemplated running from the house, past the strange little man carrying the contract I had just signed. I wondered if any girl before me had done just that. Instead, I turned and made my slow ascent up the staircase. My shaking hand gripped the handrail, keeping me steady as I put one foot in front of the other, moving closer and closer to Mr. Mason and the loss of my virginity.
I walked down the hallway and stood for a few minutes in front of the bedroom door, staring blankly at its oak paneling. I thought about the strength of oak, and realized the door would be difficult to break down, should Mr. Mason decide to lock me inside. For some reason, the thought made me more anxious to cross the threshold to the unknown. I knew that come morning, I would no longer be a virgin. Yet, I had no real idea what could happen to me from now until then.
Instead of knocking, I slowly opened the door to the bedroom. I could tell the blinds were closed and the light wasn’t turned on, but the room wasn’t completely dark. Flickering candle light, coming from about a dozen different sources throughout the room provided soft lighting.
Mr. Mason was waiting for me, standing in the middle of the massive bedroom. When he first greeted me at the front door, he was wearing crisp new denims and a dark blue golf shirt. He had change, and was now wearing a pair of silk pajama bottoms and a silk robe, which tied at his waist. If I hadn’t previously conjured up the mental image of a Sinatra-like playboy at our first meeting in his entry hall, I would have during our second encounter in his bedroom. His room was dark and masculine, yet I confess I didn’t pay much attention to the details of the room, as its master held my full attention.
I do remember there was a fireplace along one wall. It was barely autumn, and it still felt like summer out, which is why I was wearing a sundress and sandals, and why there was no fire in the fireplace. But, there were half a dozen candles on its mantel, each lit, each flickering. Candles were also placed on his dresser, and at a table at one end of the room. There weren’t any candles on the tables next to his bed. I later wondered if that was intentional, to keep a blazing weapon from a nervous and potentially reluctant virgin.
The only other thing I remember about the room was the bed. It seemed massive, yet of course it was just a king size bed. But, for a naïve, inexperienced eighteen year old virgin, it seemed as if it was the biggest bed I had ever seen in my entire life. It was a four poster bed, with sturdy oak posts, and its mattress was higher than most beds, which I later learned came in handy when a man wants to mount a woman from behind. Those posts also had a purpose - ideal for bondage.
Mr. Mason stood before me, looking me up and down. He seemed pleased with himself. Nervously, I let my purse slip from my hand and it dropped to the floor.
“What do I call you?” I wasn’t asking because I really wanted to ask the question, but I was nervous; I didn’t know what to say and felt compelled to say something, anything, and the inquiry seemed less ridiculous than the other questions that popped into my befuddled brain.
“Mr. Mason. Call me Mr. Mason. I am much older than you, and it would be improper for you to call me by my first name.” I will confess; his answer floored me. It was the last thing I expected him to say. I already knew his name was Robert, which could mean he went by Rob, Bob, Robby…a half a dozen possibilities, but his surname? I nodded blankly; his answer making him seem a bit more intimidating than before, if that was possible.
“Let’s take this off.” He said quietly as he reached his hands up, around my shoulders to unfasten my hair ribbon, freeing my hair from its restraint. I hadn’t expected the first thing he would remove was my hair ribbon. His fingers combed through my hair, arranging my curls around my shoulders.
“That’s much better; you no longer look like a child.” He smiled at me, yet his expression was still somewhat sober.
I looked up into his face, mesmerized by his dark good looks. I moistened my lips with my tongue and before my pink tongue slipped back into my mouth he leaned toward me and took a kiss. It was my first man kiss. I leaned toward him, standing practically on my tiptoes and in my own awkward way, tried to kiss him back, slipping my over eager tongue into his mouth.
After a few seconds, he pulled away from me and looked puzzled.
“Have you ever kissed a man before?” I nodded no, and he seemed extremely pleased. “Has anyone ever touched your breasts before?” I blushed at his question and immediately thought of Amy. I looked down at the floor, unable to look him in the eye. I intended to keep the secret of Amy, but I felt powerless to refuse doing whatever he asked, including answering his questions truthfully.
“Angela,” it was the first time he said my name, and instead of the Angie my friends called me, he used my real name. “I want you to slip off your shoes and climb up on the bed. Go.” He pointed to the bed and watched me as I kicked off my shoes, and climbed up onto the bed, which was not an easy task considering its height.
“Say my name Angela.” He made the command as he stood by the bed, me sitting in the center of the mattress, feeling a bit like a child who had snuck into her parent’s room. I felt very naughty.
“Mr. Mason.”
“Now, tell Mr. Mason who touched your breasts, Angela.”
I was nervous and I awkwardly tugged at the hem of my short sundress, which kept riding up my thighs, exposing a hint of pink silk and lace panties. He was waiting for my answer, so I took a deep breath before I began.
“It was my best friend, Amy.”
“Did she touch anywhere else?”
“Yes.”
“Where?” At this question, I nervously brushed my hand over my lap to indicate the spot.
“How often did you let Amy touch you?”
“Just once. It was a couple of months ago…we had too much wine….we had never done that before…Amy has a boyfriend..”
“Was the boyfriend there, when Amy touched you?”
“Oh no!” I looked up, a bit horrified at the thought, yet….
“Did Amy put anything inside you?” I could feel myself turning bright red. He smiled at my deed blush. Yet, it didn’t stop him from expecting an answer.
“Her fingers.” I whispered my reply.
“How many fingers?”
“Three…I think.”
“Did she put anything else inside you?”
“Anything else?” I sincerely had no idea what he meant. He didn’t know how little I really knew of the world. He reached down and opened the drawer on the side table by the bed. He pulled out a large dildo that looked like an enormous penis. I had never seen one before, and at the time, I had no clue what a dildo was.
“This? Did she put one of these inside you?”
“That? Oh no, something like that would never fit inside me!” At the time, I meant every word. I could not fathom anything of that size would fit inside me.
He laughed at my response and then opened his robe and pulled down the waistband of his pajama bottoms. His cock sprung out, fully erect. I had never seen a man’s penis, not even a picture of a man’s penis. This was long before the Internet. I had seen my younger brothers naked over the years, but their penises were soft, flaccid, small little things that dangled between their legs harmlessly. This man-sized penis was actually larger than the dildo he had just showed me.
I would come to realize, in later years, that Mr. Robert Mason had a very, very, very large cock. It would probably go down as the largest erect cock I would ever witness. It was definitely not the right size to initiate a virgin. Yet, at that moment, I assumed all man-cocks were the same size, each equally threatening. I decided at that moment, I would remain a virgin. There was no way in hell I was going to let him hammer that immense organ inside my body.
I started working my way off the opposite side of the bed, away from Mr. Mason. Before I made it to the side of the bed, he lunged forward, and grabbed my ankle, pulling me to the center of the mattress, and then straddled my squirming body. He seemed to be enjoying my struggle, as I wiggled and squirmed beneath his weight. I started to beg, pleading with him to cancel the bargain, telling him there was no way his penis would fit inside. I was panicked, in tears, sobbing as he methodically tied my hands to the massive oak bedposts at the head of the bed. I have no idea where he got the ropes. One minute his hands were empty and the next they had ropes; ropes to bind my hands, over my head, onto the headboard.
I was really crying by this time, and it didn’t seem to faze him. He was much stronger than me, and my efforts to fight him off reminded me of an gnat trying to fight off a tiger. After he secured my hands, he then tied my feet to the bottom posts of the bed, so that I was spread eagle, my dress now hiked up around my hips.
I felt the mattress dip and rise as he got off the bed for a moment and he quickly shed the rest of his clothes. My cries were muffled now, with tears streaming down my face. I stopped sobbing and opened my eyes, realizing I was alone. But he returned, in his hand a damp wash cloth.
Mr. Mason climbed onto the bed and gently washed away my tears and kissed my face.
“Don’t cry Angela, I know you are afraid. I will hurt you, but you will survive.” He kissed my lips, yet didn’t try to French kiss me, just soft kisses, brushing over my face.
I trembled as I watched him lean over to the nightstand and pull out a scissors from the drawer. I didn’t know what he intended to do with those scissors, yet he had promised he wouldn’t scar me.
He moved between my legs, not sitting on me, but between my spread thighs. He set the scissors on the mattress beside him, then reached up and carefully lifted up the hem of my dress, placing it across my belly as he exposed my panties. I knew they were damp in anticipation, and I was embarrassed at the thought he would soon discover my shame. While I was terrified of him, my body was already wet and moist, practically cheering on his cock.
His right palm brushed over the front of my panties, feeling the soft curls hidden beneath the lace, and his thumb moved outward, stroking my clit through the silk. He chuckled the moment he felt the dampness, and then took both hands and started to tug the panties downward. They wouldn’t go far, considering the angle of my thighs, my legs already spread wide as possible.
“I will reimburse you for your clothing.” He murmured, and then I understood the reason for the scissors. Silently he cut through my new panties, cutting them from my body. He held the moist silk to his nose briefly and drew in a deep breath. The scent seemed to intoxicate him.
He continued using the scissors, snipping through my favorite sundress, tugging it from me and then he cut through my bra straps, freeing my breasts. When he was finished, he put the scissors away and threw the clothes on the floor.
“Mr. Mason,” my voice was raspy, “can I have a drink?”
“Are you thirsty?” He lifted one brow, almost amused.
“Wine perhaps? Something with alcohol..please…it will make it easier for me.” I remembered how I felt when I was with Amy, how the wine made it easier for us. I needed to get a little drunk before he continued.
“No Angela. I won’t give alcohol to a minor; you aren’t twenty-one. And even if you were…I still wouldn’t. I want you completely sober. I want you to remember every minute of this.”
I lay perfectly still, the room seemed so quiet as light from the flickering candles danced along the walls and ceiling. It was hard to imagine it was bright daylight outside while so dark and quiet in this upstairs bedroom of the Victorian, where a young virgin lay helpless under the weight of a stranger.
He was taking his time, feasting on my flesh, starting first with my breasts, which he suckled, in much the same way I had done to Amy’s. I will confess it felt good, and I started to squirm again, not so much as an attempt to get away from Mr. Mason, but restlessly, as if I wasn’t sure what to do with my body, or what was happening to it.
His large hands moved over my skin, as if he was taking inventory with his open palms. Long tapered fingers explored me, running over my waist, along my inner thighs and circling my belly button. His fingers mischievously flicked the tips of my nipples, bringing them to hard little nubs, which he then took again into his mouth, sucking deeply, with no regards to my tender feelings or my tender breasts. His mouth moved from one breast, and then to another, like a greedy little boy determined to have it all.
He got up briefly, again reaching for the side table, pulling out some scented oil. Holding the bottle over my belly, he let the oil drizzle out, I could feel the cool liquid as it touched my skin. He liberally applied the oil, then said something about the oil making it easier for me.
After setting the bottle on the nightstand, he rubbed the oil over my belly and then down over my curls, using the palm of his hand. He moved closer, over me, and his hands slipped under my buttock, over my butt cheeks, his hands pressed between my bottom and the mattress.
I could feel his fingers spreading my butt cheeks apart, and I was horrified to feel one of his fingers wiggling its way into my crack and into a place I never imagined a man would insert his finger. I gasped. He chuckled.
“Oh sweet Angela, I would take you there, but I’m afraid I am far too large to fit, without doing real damage. But remember Angela, when you choose to sell that, I know someone who will pay the price.” He kissed me deeply then, moving his hands away from my bottom, and pulling himself over me, settling his hips between my thighs. As he positioned himself, I felt his hard cock move over my belly. I was confused, and had no idea what he was talking about.
I had no time to ponder his comment, for before I knew it he positioned the head of his cock at the entrance of my womb and gently moved its tip in and out of me, in seductive little strokes. The bulging head of his cock could not get beyond the tight opening; it refused him entrance.
I could feel him trying to enter me, and I knew it was impossible. I began to plead for him to stop. Silly me, I had no idea how hard he tried to ease his way into me. I didn’t know that if he wanted he could send his cock deep inside me, with one thrust from his powerful body. He was gradually stretching me, preparing me for his cock’s length and width, yet I didn’t understand, because each time the head of his cock made it a little farther inside me, it hurt more. I assumed he was already deep inside me, yet he had only just begun and had barely entered me.
I was hot and flushed, drenched from sweat and I trembled. The only sound in the room was the heavy deep breathing of Mr. Mason, as he loomed over me, his heavy body holding me prisoner. Tears were silently flowing down my cheeks again as he gradually entered me, time and time again, the head of his cock barely making its way inside me.
Foolishly, I bucked, wanting escape, yet my futile attempt was too much for the man who was trying to maintain his control. He swore under his breath and then plunged his cock deep inside me, ripping through any virgin barriers, staking his primal claim on my body. I screamed, loud and wildly. Yet, he didn’t stop. His hips were thrusting, pumping his cock deep inside me, then pulling out, leaving just the tip of the cock inside, before entering me again.
Again and again, his cock moved in a primal rhythm, pounding away, forcing me hard against the mattress, I could practically feel my head bouncing up and down off the mattress. After the initial pain, which was great, the sensation became somewhat pleasant, yet still painful.
The thrusts became like a rhythm of life, calling me, seducing me. I found myself moving into each thrust, welcoming the invasion. I moaned, sobbed, and moved my hips to reach some unknown pinnacle. Suddenly I felt his release. He held his cock deep inside me and I knew, knew he was filling my womb with his cum.
I wanted to cry, not because it seemed to be over, but because he was finished and I needed something else. I was almost there…almost.
He rolled off me and could see I was sobbing again. Instead of leaving me, he moved one of his hands to my curls, which were now drenched in my virgin blood. As if he knew what I needed, his fingers worked magic, doing to me what Amy had done, but it was much more intense.
I shamelessly pumped my hips, taking his fingers inside me, and trying to spread my legs even wider than they were, which was impossible, considering I was still tied spread eagle. When I finally came, Mr. Mason kept his fingers deep inside me, feeling the spasms of my orgasm.
While I lay there quietly, like a wrung out doll, Mr. Mason removed the ropes. He gently washed my wounds, mopping up the sticky mixture of blood, oil and cum. I wondered when he would send me away, but I discovered he wasn’t done with me.
He filled the large bathtub in the master bathroom with warm water and led me to it. Without speaking a word, he bathed me. The water eased my wounds. I was so tired and ready to go home. He wrapped me in a large fluffy white towel. It was warm and toasty. I was so sleepy. He led me to the bed.
“Will you give me clothes, so I can go home now?” I asked softly.
“No Angela, you belong to me until morning. I am not done using your body.”
I didn’t care for the way he said he was using my body. It made me feel odd, uncomfortable and in some way shameful. Yet, there was a hidden part of me that wanted him to use me - to fuck me again. I wanted to come while his cock was inside me, not his fingers.
He finished drying me and then told me to get back up on the bed. Yet, instead of me laying on my back on the center of the mattress, he told me to get on my hands and knees, with my bottom facing out, over the edge of the mattress. I didn’t understand, and the position embarrassed me. This was the first time I had ever been with a man and the idea of my ass sticking out over the bed seem strange. But I did as I was told, because I didn’t want to get tied up again and I knew if I refused he would force me, and I figured that whatever he planned, it would hurt more if I fought him.
I couldn’t see him, but I knew he was standing behind me, looking at my bottom. He gave my bottom a firm slap and told me I had a great ass, almost as good as my tits, and if he was ever to fuck someone who wasn’t a virgin after this night, he would be tempted to take me again. I will confess; I was flattered. After all, it was something Jill desperately wanted.
I could feel his hands on my rump, and I knew he had the oil out again. He was massaging my bottom with the oil, and I never knew, until that moment, how much I liked the feeling of a man’s hands on my ass.
I wiggled my butt just a little, encouraging him on, like an eager puppy for a treat. In my innocence I thought he only planned to rub my ass, I had no idea he intended to take me from behind, to mount me like I’d once seen a stallion take a mare. I didn’t know men and women could have sex that way.
He pushed my knees a bit farther apart as he positioned himself behind me, and moved the head of his cock to my entrance. His hands grabbed firmly onto my hips, one hand on each side, as he slowly entered me from behind.
I gasped in surprise. I was sore, but his entrance didn’t hurt like before. I moaned as he pushed slowly inside me, as if he intended to take his time. As he moved his cock in my sore entrance, I could feel his fingers spreading my ass cheeks, and one of his fingers pressed into that other forgotten place, deeper and more persistent than before. I cried out in surprise, but he only laughed and then began pounding me, riding me like that stallion rode the mare, with total dominance and authority.
I took it. I pressed my ass back, taking the length of his cock and enduring the invasion of his finger in that other place, that place where I never imagined a man would touch. He fucked me hard and rough, I could feel my breasts sway beneath me with each forceful ram of his cock. And then I felt it, I felt it build again, that place I wanted him to take me while he was still deep inside me.
I was afraid he might stop, so I told him to fuck me, I yelled it, pleaded with him to push deep inside me, to take me however he wanted, that I wanted whatever he wanted to give me. He complied, fucking me hard and deep until I felt my womb convulse. He plunged one final time inside me, and held my hips firmly as he kept the full length of his cock buried inside me. As it filled me, I felt myself come, my womb squeezing him, milking him of the last ounce.
We collapsed on the bed, exhausted, and both fell asleep. Later that night we woke up, and he took me again, this time slowly, softly, and again I felt a blissful release.
Before I left him, we talked while lying in each other’s arms.
“Angela,”
“Yes, Mr. Mason.”
“I enjoyed your body, I enjoyed you. You were a delight.”
“Thank you sir. I…I also enjoyed it.” At this, he chuckled.
“So, you forgive me for tying you up?”
“I thank you for tying me up.” Now he laughed.
“Angela, I want you to know, I have never been with a virgin that has such a natural propensity for lust. If I was a pimp, I could make a fortune off of you.” I wasn’t sure if his comment was an insult, or a compliment, so I remained quiet, yet snuggled closer to him, enjoying our last minutes together.
“Angela,”
“Yes Mr. Mason?”
“Did you enjoy it when I pressed my finger in your ass?” I was too embarrassed to answer, and turned my face away. He laughed again, and gave me a quick hug.
“Angela, some men like to take a woman in that place, not just with their finger, with their cock.”
“Really?” I found it hard to believe.
“Yes. In fact, I have a friend, who like me, has his own virgin preferences. Before you let a man take you there, come to me. I will arrange it. And Angela, it will fetch you much more than what you made tonight. But don’t think about it now, this is all new for you, and I imagine it will be a while before you are ready for a man to take your ass.”
If ever, I thought silently.
I fell back to sleep, and when I awoke in the morning he was gone. There was a new dress, panties, and bra laying on the bed, all in my size. There was also an envelope; instead of a $1,000, it held $1,500. I didn’t stop to think about my actions, that in effect I behaved like a prostitute. I suppose I did think about it, yet rather than making me feel shameful, I felt naughty and sexy.
I dressed; found my purse, which I had dropped by the bedroom door, and took my money and left the home of Mr. Mason.
On my walk back to the campus apartment, I thought about the events of the previous evening, and wondered where I would find my next sexual encounter. Life was good.
I hope you enjoyed the story and take the time to leave a review.
Selling Her Cherry is a revised expert from
In Search of Angela, First Encounters.
Look for my other erotica short stories on Smashwords.
Maggie Chatterley
https://www.smashwords.com/profile/view/MaggieChatterley