Breaking Him

I was 20 and had just moved to Boston. I didn't know many people and had yet to find a place to live. I was still living with my brother. On a trip to the supermarket I noticed an older woman in the checkout line giving me the eye and a wide smile. Being the shy type I didn't reciprocate but managed a weak smile and nod. I paid for my groceries and left. I noticed the woman outside on the sidewalk struggling with her many bags. I couldn't stand there and not help so I went over to her and asked if she needed assistance. Her face grew into the smile I had seen earlier and I managed the carry the brunt of her shopping to the home.

As we walked I sized her up. She had long auburn hair, cute face, full breasts and a great body. She was shorter than I, but most women I had dated were shorter than my six feet. She asked about myself and I told her how I had come to Boston and what my plans were. When she asked I told her I had no girlfriend, after which she promptly invited me in to dinner.

Reaching inside the bags I had carried, she took out pasta, meat and sauce. While she whipped up a batch of spaghetti we talked about ourselves. She had been married once, long ago when she was my age. She was 15 years my senior and is now looking for something a bit different. She said she had been around the country and I listened to her as she talked about her travels.

Dinner was ready and I we sat down to eat. Not sure of etiquette, I pulled her chair out for her and helped her sit. I laid the napkin on my lap as we ate. We didn't talk much, both being very hungry. When dinner was over I looked at the clock and then noticed how dark it was outside. I had to be leaving soon and she seemed to sense this. "You don't want to be late, you better head home hon" she said as I frantically jumped from the table. I grabbed my jacket and she met me at the door. As I turned to leave she grabbed my face and gave me a deep openmouthed kiss. For the seconds our lips touched I was lost. I felt something pass from me to her in that connection, something that would change me forever. She slipped her phone number, written in long feminine script, into my hand and told me to call her sometime.

I thought about her all night. When I finally did sleep she appeared in my dreams, her lips touching mine, her pulling me to her.

The week passed by slowly and I finally screwed up the courage to call her. She answered the phone on the first ring and greeted me by name when she heard my voice. Though I tried to play it off I'm sure my voice must have shook as we talked. I cursed myself; here I was an attractive twenty year old with enough bedroom experience to fill a lifetime of fantasies and I was tongue tied talking to this beautiful woman. I can't remember much of the conversation, her voice had turned me into a voiceless automaton that could only answer in monosyllabic words and fake laughs but I remember her inviting me over that weekend.

As I readied myself for our date I thought of how things would be different. I would meet her at the door, ask her if she was ready, and swoop her away to a night together. I dreamt of her in bed, my fingers teasing her nipples, my tongue tickling her inner thigh and I felt myself grow aroused as I bathed myself.

She wore a long flowing dress and silken scarf that hung from her neck as I met her at the door. As she ushered me in I could smell a sweet aroma from her body. Strawberries? Vanilla? Jasmine? I couldn't name it but already she had me stiffening under my clothes. She grabbed my hand and pulled me to her car, where I sat on the passenger side. We had reservations at a French restaurant, she said. It was dimly lit, with a candle between us an freshly shined silver.

Her eyes never left me the entire evening. I felt like the prey, she would be the predator. I felt myself drawn to her the entire night. I had to have this woman! She was the most alluring creature I had ever seen. Just the thought of her gave me a feeling that made my legs weak. When I picked at my food, she urged me to eat, "We don't want to leave anything to waste. That wouldn't be proper for such wonderful food." Instead of going to her house she dropped me off at mine, where she turned to give me a bg hug. A shiver ran down my spine as her fingers ran through my hair as we kissed. I truly was hers. She knew how to play me, how to make me feel. As I watched her drive off I realized there was nothing I could do. I couldn't see other women, they held no interest for me now. Instead, she appeared in my fantasies every night where we would play another game or one more position.

It continued this way for weeks. She would pick me up and we would go either to dinner or a show, even a movie, return home, a kiss and a goodbye for the next week. I grew discouraged. She called me midweek one time, a break from our routine and instructed me to meet her for dinner at her place that Friday afternoon. She advised me to bring a toothbrush and a change of clothes.

I waited impatiently for the week to end and come Friday I ran out the door and to her home. She called from the kitchen to come in as the door was unlocked. I dropped my bag in the foyer and found her in the kitchen. She was making Chicken Cordon Bleu and told me to wait at the table until she was ready.

Tonight was the night! I couldn't wait and imagined us together in bed soon. I was restless and my fingers tapped on the table as she spoke from the kitchen. "We need to have talk, sweetie. There are some things we need to discuss."

My heart dropped. Was this THE talk? I didn't want to lose her. At that moment she came walking through the door, her arms cradling two large portions of dinner. "But for now we will eat. The discussion will come later." I nodded and dug in.

Dinner went well and I told her about the new job I had just begun that week. She was warm and laughed throughout the meal.

We finished and she took the plate from me, depositing it in the sink. She brought her chair closer and sat down, our knees almost touching.

"Kevin, I have grown to really like you these past few weeks and I want us to continue the direction we're in." I agreed, nodding quickly.

"Please don't interrupt, let me finish." She corrected. "You need to know this if we are to have a relationship." She held my hands and looked me in the eyes. "I have been through many relationships, most of them bad, and feel I must be true to myself now. If we are to see each other you must do as I say at all times."

I was shocked. I had never heard a women talk this way to me before but I didn't dare say a word. "I have found most men are selfish and care only for themselves. You seem different and that is the reason I care for you." She smiled again, giving me a warm feeling inside. "But you are young and still very headstrong. At first I thought that would cause problems and it wouldn't work but I decided to give it a try." She touched my cheek with her hand then, caressing me softly. I closed my eyes and listened. "If you care about me and want this to work you will do as I say, any failure to do so will result in discipline." She smiled then as she saw the look on my face. "Don't worry, sweetie, nothing you can't handle, but it must be done if we are to work."

"Now, let me ask you this, have you thought about making love to me?"

I responded that yes, I had.

"I have thought about it as well and I apologize for being so unresponsive but I must be sure everything is right between us. I would like to make love to you but to be fair I must let you know what you are in for." She stood me up and looked me over. I was aware of my excitement and knew she would be as well. When she finished she stood a foot away from me and looked into my eyes. "Take off you clothes, sweetie. I want to see you"

I hesitated for a moment, unsure of my next action. As if in a trance I began to remove my shirt, my shoes, then my pants. I was in good shape and knew she would be pleased with me but felt awkward to be treated in such a manner. I wore only boxers now and slipped them down my legs. My erection stood out and I covered myself with my hands.

"No no, move your hands. I want to see all of you" I did so, gritting my teeth. It felt like the rug had been pulled out from beneath me but I stood my ground. She walked to me and turned me around. I felt her hands on my back, thighs, ass and balls. I shook from her touch.

"Very nice, sweetie, I love your response." She took my hand and walked me into her bedroom. I realized it was the first time I had been in the room. It was large and open, with a four poster bed at the other side. She had a night table with a vase filled with four roses. A small bowl of potpourri filled the room with the scent of cinnamon.

I turned to her, reaching out to take her in my arms, but she only spun me around so I faced the bed. "Bend over, sweetie"

I remembered what she had told me before and didn't want to disobey her. Her sheets were smooth and soft and felt good pressed against my swollen cock. I heard movement behind me and looked over my shoulder. She was in the closet, searching through the top shelf. She turned and saw me looking and yelled at me to turn around. She was behind me now.

"You must never look back when you are being punished. That will only make it worse. I am going to show you what happens when you disobey me. Sometimes it will be severe, sometimes it will be easier but I want you to remember you are doing this for us and to be strong."

I can honestly say I had no idea what I was in for. Any moment I expected her to turn me over, jump into my arms and tell me it was just a test. I didn't brace myself for the first strike because I never saw it coming. I felt it though, a searing pain that stretched across both buttocks. I clenched the sheets as more attacked my vulnerable backside. I clenched and tensed every muscle in a vain attempt to ease the pain but it was no good. Before long my entire body shook from the pain and I felt my eyes cloud with tears. I had never cried in front of a female since I was a boy and refused to do so now.

She continued the punishment and seconds later I felt warm, wet tear slip down my face. My body felt like one massive organ, my bottom between the apex. I heard her behind me delivering blow after blow to my helpless body and braced myself. My ass was screaming in pain and I bit down on my tongue, only hoping it would end soon. It felt like hours passed though it must have been only 30 minutes.

Finally she stopped and my body was shaking. The sheets were wet with my tears and I was numb to everything but her.

"That's enough for now, sweetie. Stand up and give me a hug." I managed to slowly stand on wobbly legs and fell into her arms. She rested my head on her shoulder and we stood that way for a while, slowly swaying together, as if in a dance.