Carla has visited my NYC office on many occasions. She is a product manager for one of the lines of formal female dress shoes my stores and consignment partners carry. Once she had a late flight and had to check out by noon from her hotel. I let her put her luggage in my storeroom and offered to make her dinner at my week-day apartment just around the corner. She felt safe with that. I’m twelve years older; we have a working relationship to protect; we had little time before her flight and I had no plans to take advantage of her.
Before dinner she browsed through my very nice but not ritzy penthouse; nothing close to the down town multi-million dollar ones. She was a little late making it to the table after I had everything ready. Her face was flushed and her eyes sparkled. She did bow her head trying to hide her eyes and embarrassment.
“What’s wrong Carla?”
“I looked in your bedroom.”
“I should have locked that door.” I poured her chardonnay, “You are a beautiful woman, well out of your virginal teens, what embarrassed you?”
“I’m a dominant, playful, oral male who enjoys women and fetish art – no real pain, just D/s play.”
We had a wonderful meal filled with pleasant conversation. I learned a lot about her small town upbringing with her homemaker mother, her proper finishing school education and rather militant feminist activities during college. I mostly listened. My few words kept her going and her words poured out, telling me a lot about herself. We left the dirty dishes on the table after desert. We had no extra time. We had to get her to the airport. During the drive she divulged a couple more things and learned one that made her gasp quietly.
“You really practice the Dominance and submission, male over female things in your life?”
“D/s works both ways. I don’t need or want a slave, but the women I chose want to feel power, be protected and serve in return.”
“I don’t believe in that role playing stuff. It’s silly to me. I don’t need that.”
“We had whipped cream in our dessert. If your favorite date, tied a napkin over your eyes, stood behind you and put a spoon full of whipped cream on the front of your neck so it would melt, run down into your dress and across your breasts, would you stop him? Or would you let him kiss you deeply, hold your hands behind you, trapped between his thighs so you could feel his cock grow from wanting you. Could you enjoy feeling him lick and kiss your body, while he sucked the cream from your breasts and inhaled your pheromones. Would you feel power over him knowing your wonderful body was stealing his intelligence and making him insane wanting more from you?”
We drove up to the unloading area for her airline and I helped her out of the car and unload her baggage. I tipped the porter and then grasped the collar of her coat, “This is very unprofessional.” I pulled her to me, she exhaled and I sucked in her breath. My tongue licked at her lips and I filled her lungs with my breath. Her eyes were dreamy. I left her with only one thought.
“Thank you for visiting with me tonight and then sharing some verbal play. I will go to sleep tonight with the Dominant fantasy you allowed me.”
The Christmas season was wonderfully profitable. I received a bonus from Carla’s company. It wasn’t much but I wanted to spend it on her. She had resisted twice over the telephone but nature made our decision. I had not seen her for three months. In late January, she arrived in New York for only one night but that night it snowed. I slept in at the townhouse. She slept in her hotel. The next night was Friday the airport was still horribly backed up. Her flight had been canceled. Almost everything else was open. I couldn’t get to my home in the suburbs according to my neighbors. We met half way at a famous restaurant where I frequently dinned. It was slow enough that my favorite, blond cougar waitress had time to cater to us. We had teased often but she said I was too old for her. She is Carla’s age but far more verbally playful.
Carla and I knew we had nothing to do but spend the evening dinning, so we took our time. She was dressed in a black form fitting dress with a plain black nit band around her neck. For over an hour we delayed ordering and got into our second bottle of champagne. She turned the conversation quickly and shocked me, “You surprised me, when we had dinner at your house.”
“How so, pretty lady?”
“You twisted things and I almost believed in your D/s fantasy.”
I felt her disappointment and challenge. I took all the keys off my inch-and-a-half diameter gold plated key ring, complete with four links of matching chain. She looked puzzled. “The restaurant is only half full tonight. Will you play and experiment with me here?”
She did not answer but her eyes were full of questions. Our waitress arrived with some stuffed mushroom appetizers just as I asked Carla if she thought such a small thing would make a difference to how she felt wearing her wardrobe tonight?
Indignantly Carla answered, “No, it might look silly but a gold ring would not be noticed by anyone.”
I scooted closer. The waitress had to move. I put the ring through the material on the front of the black stretchy band around Carla’s throat. It hung freely and visibly down from the middle of her neck. My waitress looked at her smiled and said, “I’ll give you two a little more time to decide on what you want…(she paused)…to order, that is.”
Several of the female restaurant patrons pointed and whispered to their partners. The light was starting to come on in Carla’s rebellious mind but she still was puzzled.
“You are announcing proudly to the world that you are mine tonight. Whatever I want, you will willingly do to please me. You are proud to be submissive and will follow my lead to give us both pleasure.”
Our waitress arrived again; she whispered so Carla could hear, “God that’s hot.” She looked at me and continued, “We never finished our last conversation.”
From my inside coat pocket I pulled out an ad for the best kangaroo cat-of-nine tails made by a prize winning Australian whip maker. As I unfolded it, I talked to our pretty waitress, “Next month is my birthday. See what present I ordered for myself? Remember I told you the last one was too hard and harsh. Even when used lightly, it would have left welts instead of erotic stinging stripes for me to kiss and leave you dripping down your thighs.”
Our waitress put her pad down, lowered her eyes and held on to the edge of the table imagining the sting while still viewing the beautiful red whip. Her breathing was irregular but she gathered herself together enough to ask, “When you get it, will you bring it in so I can feel its leather braids?”
I asked her, “Do you want to touch one and smell the leather or do you want to feel the tassels and imagine them lash across your naked ass?”
She almost came. Months and months of teasing conditioning with a woman, who sometime in her life had willingly felt an expert’s hand with a whip, had paid off. She was frozen.
“Carla, show me you have the guts to try and understand power play. Reach under her skirt and see if her pussy is wet.”
Carla’s eyes were bulging. Her body trembled at my challenge She needed to prove she was as sexually adventurous as me. Our space was secluded. Her right hand reached across her body and slipped under our waitress’s skirt. I could see the waitress uniform move as Carla’s fingers rubbed and thrust and pinched. Our waitress broke all the rules and sat down in the empty chair separating Carla and me. I would not let up, I whispered, “When you come back with our salads, do not have panties on. Carla will push two fingers into you and will feed me your wetness. I’ve always wanted to taste you.” Her mind was spinning, her eyes did not focus and she stumbled twice making it back through the dining room to get to the kitchen.
Carla was statue still.
“Was she wet?”
“Go ahead, taste her.”
With only a moment’s hesitation, Carla licked her fingertips.
“Your decorative neck band is now seen as a sub’s collar by everyone, male and female. You are allowing me to direct you and your body is responding to its own submissive advertisement. Do you feel its demand to please and be pleased?”
Our salad arrived and Carla almost put our waitress into a screaming orgasm. The black and white French maid’s outfit seemed out of place sitting with us while Carla’s wild eyes and nervous shaking fingers fed me our server’s slippery, stringy, dripping wetness. Carla went back for seconds because I finished the first course. I saw Carla’s hand tremble when her fingers entered our waitress and her thumb began to molest another woman’s clit. I challenged our waitress, “Bet you didn’t get to her at all. I bet she is as dry as the desert. Prove me wrong.”
Our waitress was worked up, got strength from my words, stood, put her back to the sparse crowd and literally crammed her right hand between Carla’s thighs and drove two fingers past her panties’ legs. Carla set upright and rigid. I waited. Her mouth opened and I pushed a piece of warm French bread into her mouth for her to bite and scream into. A couple of minutes later, Carla’s eyes rolled back and her body shook for a few seconds before it visibly relaxed. Our waitress touched her wet slippery fingers to my lips. I licked. She left. In another minute, Carla whispered, “I wet my skirt and the chair.”
I had to admit to her, “You should have been sitting on my mouth and I would have swallowed everything, keeping you dry and not embarrassed.”
After the entre, Carla made a trip to the ladies’ room to “freshen up.” I made a mad dash three doors down to get her a present. I was back in place by the time she returned; coffee and cheese cake were served; she had dried most of her wetness but I could still smell her because I wanted to.
A super big tip was in order for our waitress. I also told her when my cat and I would be back to see her. When I walked Carla to her hotel and left her at the door, I gave her, her present. “I want you to do me a special favor. Take your present and when you are finished, immediately call me, regardless of the time and tell me “good night” so I can hear your satisfaction.”
She looked confused but she would understand when she un-wrapped the expensive vibrator that would help her relax and then her breathy words would help me sleep.
Carla called me from the airport just before her boarding call, “That was wild and out of control at the restaurant last night. And later the phone sex was hot when you made yourself cum on your stomach for me. You won’t tell anyone will you?”
“I hoped you know me better than that. I will never tell anyone. Remember, you know some of my secrets too. You were every man’s fantasy last night. You still have me crazy wanting you. I’m so happy you felt safe enough with me to let yourself experience a little D/s play. I feel closer to you this morning. Remember me once in a while when you are being pursued by all the handsome young studs that drool behind you at all your worldly stops.”
There was a pause, she started to say something but quickly interjected, “Oops, there’s my boarding call, I have to run. Will call you in a few days and tell you when the spring designs will ship.” I don’t think she heard my “Goodbye.” She was off, back into her bustling world. As I hung up the telephone, I hoped she took my gift, would use it often and remember the new experiences she had last night.
That same night, I had a text from Carla, “Would like to talk to you privately. Can I call you at home? When? Number?”
I texted back with my private cell number and suggested after eight p.m. or anytime on the weekends, “Will enjoy talking with you any time, any place; you are exciting and delightful but still a mystery.”
Carla was in California. It was ten p.m. on the east coast when my phone rang, “Is it too late to talk?”
“No, Beautiful, I don’t need to sleep, if I can talk to you.”
“Are you always like this?”
“You’ve worked with me on a purely business basis for three years, what do you think?”
“Ok, true, you have only been playful since the night I had to stay over in New York because my flight got canceled.”
“We do have complications because we have a working relationship and I am attracted to you? I’ll back off, if all this makes you uncomfortable. But, “Yes,” in my mind, I’m always sexually playful.”
“No, no, I don’t want you to back off, that’s not why I’m calling you. Our dinner, our play with the waitress and you, in general, put some much needed excitement back into my life.”
“Again, “put” is past tense. Talk to me. Ask me what you need to ask. It may be time we risked a little to discover some unknown possible beauty.”
“Matt, I enjoyed our dinner, your gift and spending time with you. I’m wondering where you are trying to lead me and if I can go there.”
“Carla, you are making too much out of the D/s thing. I’ve been married twice. The first one lasted twenty five years until Millie died. We had four kids and a good life. We had a good active, equal sex life and never even role played in the D/s lifestyle, other than maybe tying each other’s hands to a bed post. My second marriage lasted five years and was about the same sexually. Susan liked different things. I liked her creative naughty mind, but I couldn’t tolerate her affairs. The D/s thing came from a two year long relationship I had with a girl who wanted to go much further into the Lifestyle than I was willing to go. I can live with it or without it. I do enjoy the power exchanges, watching the far more intense climaxes of a woman who can let go enough to spiral into sub-space and her willingness not to hold back any part of herself from me. I’ve only had one such relationship.”
“What happened to that?”
“If I talk any more about this, we’ll have to be face to face and you’ll have to understand a little more about me. I’m a gentle but alpha male, who can be very physical and is fully capable of taking what I want but only from a willing partner.”
“You said you were oral. Can you talk about that?”
“That’s pretty self-explanatory.”
“I’m sorry, Matt, but to me it isn’t. I was married for a few years. I haven’t had kids. My ex-was a violent, abusive alcoholic. The relationship ended when he put me in the hospital. I’m over forty but I’ve worked and not dated. I’ve looked at the internet and talked with female friends but I don’t know what’s true or what’s exaggerated.”
“Damn, Carla, I wish I had known all that. I’m sorry. I’ve definitely done a lot of improper teasing and playing. If you can put all that behind us, I would like to start over. I am attracted to you, really enjoy your company and am hoping we can date to learn more about each other. I’ve probably given you all the wrong ideas about me, frightened you and you only tolerate being around me because I’m an important customer.”
“That’s not the case at all. I’m attracted to you also. I’m intrigued and shocked about things that have happened. I would like it if we date. I just wanted you to know that I’m not experienced like you and …”
Her voice trailed off. “Carla we are friends now. You’ll learn I have some concerns and insecurities too. You can be open with me. You won’t shock me. Please, go ahead and finish what you were going to say.”
She beat around the bush a couple of times trying to find a way to open up. Her voice trembled. Finally she said, “All the women in your pictures are beautiful. From my ex, I have some ugly scars and permanent marks on my body. I would never be beautiful like that for you or any other man.”
I was quiet too long. She did not understand. I could barely talk. I said, “Carla, everything is fine but I have to call you back in a few minutes.”
My mind had flashed back to finding my first wife’s sister and years later having to identify my daughter’s body at the morgue. My body shook, I cried; I remembered; I pulled myself together; I practiced talking and I called Carla back.
“Sweet Thing, just listen, don’t say a word or I won’t be able to get through this. First, your scars will not make any difference to me; it is you I want to know. I might have some trouble but it won’t be you. I broke up and cried when you told me. When Millie and I got married we lived next to her older sister. One day, her sister did not answer the door. Millie said she could barely see her sister on the couch through the curtains. I broke in the door and found her beaten to death with a claw hammer. Twelve years ago, my daughter called after being beaten by her husband. I told her to come home. She was hurt more than I knew. She died in a car accident coming to me. Don’t ever be afraid of me. I can never hurt a woman. You might see me cry but your scars will not offend me. They too will be a horrible kind of beauty because they prove your strength over what you survived.”
Carla was quiet. I was too. I broke the impasse, “Carla, please call me tomorrow or when you can. Let’s start over. I need a wonderful, intelligent female friend like you. I really like you and hope things might grow between us. But let’s talk, maybe date when you are in town and see what happens.”
“I’d like that. I’ll call tomorrow.”
I could tell she was crying.
Carla and I burned up the telephone lines for a month. She’d even call me to tell me what she was having for lunch and I’d tell her I would probably still like her kisses even though she was eating onions. I knew everything from her shoe size to the stores in her home town. We were both nervous as teenagers on our first date when she made it back to New York and we went to dinner and then a play.
The next night we started earlier. It was before nine when she asked me to go up to her room with her and share some wine. We held hands and were even more nervous because we knew where this was leading. She had planned for me. After we talked for a while in the little sitting alcove in her room, she said she wanted to get into something other than her work clothes and hard shoes; her feet hurt. She adjusted the lights around the room and turned on a TV music channel, as she headed to the bathroom. I took off my shoes and tie. My coat was somewhere in the room.
Carla was blushing when she came out in the fluffy white bathrobe provided by the hotel. I could tell she had some kind of short thick cotton nightie under it. Now it was my turn – my turn, to at least claim her lips.
I met her in the middle of the floor and our first French kiss was hot, wet and passionate, like we had been lovers for years. I sat on a desk chair and pulled her to sit on my lap and kiss me again. Within seconds she knew what I was doing and she let the wetness in her mouth flow into mine. Her tastes exploded through all my taste buds. She relished me drinking from her and sought to give me more. She hovered over me, balancing by grasping my hard cock and letting me suck the wetness from her tongue as we worked one kiss into a sexual masterpiece of desire.
I was dizzy. My cock was rock hard and twisted in my slacks. Carla was as turned on as me. She threw her now too hot bathrobe onto the floor and straddled my hips. The moist heat from between her legs was shocking even though it was passing through her nightie, her panties, my slacks and my boxers. Her hips were searching for some friction for just the right spot. I challenged her, “Reach down into my slacks and pull my cock up straight so you can thrust into it.”
She might not have had many experiences but without hesitation she undid my slacks, slipped her right hand in my boxers, and rubbed her palm through the precum what was coming from me more freely than I ever remember. She reached to the base, let her fingers and thumb encircle me and pulled back half way up my cock and squeezed. Slowly I pulled my hips back, her fingers tightened and I pushed my cock through her tight fist forcing her fingers to spread.
She brought her face close to my neck, kissed and licked and then let her hot breath tell me, “You would stretch me.”
We kissed and touched through our clothing for a few more minutes. She and I worked to remove her panties and everything I had on below the waist. She thrust and felt the thrill of my hard cock spreading her pussy’s lips and the back-side of my shaft grinding against her covered clit. Finally, I picked her up, carried her to the big king sized bed and lay her down gently. I felt her tense up as I released her. She was worried about what I might see. I finished stripping for her slowly in the dim light as she had adjusted it. She examined every inch of me. When I turned away, she looked puzzled, “Pull the comforter back, while I make this a little more intimate.”
I dimmed the three way lamp in the setting alcove and turned all the other lights off. The bed was in near darkness. Only shapes could be recognized. Neither of us could see any detail on the other’s body. We would have to feel with our hands, our lips and our bodies.
We were both hot and ready. I stood at the foot of the bed; Carla reached for me.
“Spread your legs, Carla. I want to taste you.”
Her body released a soft pleading moan as she followed my instructions and laid back.
I wanted to cum but my age could hold that off. I wanted to please her and let her know that all I had said about scars was true. I wanted to know if she were noisy and wet when she came. If she could cum more than once; how rough she would be; if she could be half of what I imagined.
No other foreplay was necessary; I crawled between her legs, played with her soaking lips, trailed a finger across her clit and then slowly pushed my finger inside her to press her g-spot. My lips closed over her clit as my finger tip touched where the magic would begin. Another finger was needed. I licked, kissed, sucked, all gently, while I pressed and rubbed inside her. I heard her sounds of encouragement and felt her knees come up and flair wider. I wanted her to tell me.
In a couple of minutes, her hands gently touched the sides of my head and I licked just a little faster and harder. Her hips arched. In another minute, her hands pulled me tighter and my fingers thrust into her a tiny bit rougher in time with my tiny bit rougher licks. She knew how to direct me now. She liked to torture herself. She got close once but relaxed her thighs and her hands; I slowed and made all my touches more teasing and lighter. She had done this but her body groaned in complaint. I gently felt her pussy’s lips. They were thicker, wetter and softer. I sucked each one for its tastes and my mind spun even more.
Carla pulled her knees up with her hands and pulled them wide. She gasped when I removed my fingers and licked her tight rosebud. She decided this too was good. Ever so slightly, she pushed toward my tickling tongue, hoping it was all right that her millions of nerve endings liked this feeling. I told her “Yes” by pushing as much of my tongue up her ass and then rimming her. Her pussy was leaking enough to have juices flow onto my tongue as it was teasing her pucker. I made sure she was good and wet there.
As I worked back up, I whispered, “I can’t worship your beautiful breasts while I do this; help me; play with them and imagine I’m kissing them and kissing your lips too.”
This time I bypassed her pussy and kissed around her stomach while my now two experienced fingers re-entered her and began to thrust slowly as my cock would do. They even raked across her clit as they slipped in to kiss her g-spot before they slid almost out, only to thrust again.
When kissing above and in her pussy’s hair I felt an irregular depression with too smooth hairless skin, my first indication of her body image issues. That thought lasted about two seconds as I went back to her tasty, needy and demanding pussy. Neither she nor I were going to be able to tease it again. Carla’s pussy demanded that she press her thighs tight against my head; it demanded she grab two handfuls of my hair; it demanded that her body curl slightly to hold me tight and it demanded that I do the best job I knew how to do.
She panted, she squirmed, she wiggled trying to get over the top but her mind was still working and giving her distracting thoughts from her horrible past. Gently, I closed my teeth on her fully extended clit, I sucked a little harder and I licked the little nub that protruded past my lips. My fingers pressed her g-spot, pushing even more of her clit into my mouth. Her mind shut down and her body arched off the bed. She pulled me so tight into her mons that my face hurt and she let out the most delightful scream that I have ever heard. We humped like teenagers in the back seat of a Chevy. She demanded more release like the most self-centered person in the world. Her womb contracted, her face contorted, her scream went up an octave, I felt every muscle in her body contract and from somewhere she geysered magnificent juices into my mouth. I swallowed as fast as I could. My taste buds sung. She soaked me but kept going to do it again, and then one more time, but with just a trickle. Her body was still contracting and sucking. For some reason I went at her cunt hard and furious with my mouth. I knew most women would be too sensitive at that moment for me to be in the same room. I took two fingers from my left hand and rolled them in her wetness and then pushed them into her super tight ass.
Carla’s scream made the last one sound like a worn out gramophone. This was five speaker surround sound. I lost a lot of hair and she tore my ear with her nails. She kept going and going. I was shocked and then she totally collapsed. I knew she was still alive; muscles inside her were still contracting, sucking my fingers in both her cunt and her ass. I bit the top of her thigh hard enough to get a response from a living person. She did not react.
I crawled up to lie next to her and pulled her and her wetness to me. I covered us and she slept a couple of hours. I thought about jacking off, lost my concentration and just dozed.
Carla awoke in pure panic and fright. I hugged her so she could not move and whispered how wonderful and special she was. I told her how beautifully she came and that the vision she gave me was the most beautiful thing I had ever seen. She relaxed, rolled onto me, kissed me and her tears dropped freely onto my face and rolled down my cheeks onto my neck and the pillow. For probably thirty minutes, I held her. First her body trembled not in pleasure but fright, worry and concern. Then she began to relax with me, remember and enjoy what we had done and feel the satisfied glow in her body.
With no words she felt for my hard cock and pulled for me to roll on top of her. I resisted, pulled her and said, “You guide me into your body.”
She put a leg over my hips and guided the head of my cock. She used it to rub her clit, then she rubbed it up and down between her soaked and swollen lips. She centered it and said, “Push.” God I love team work. Slowly, both of our minds left our bodies as inch by inch my cock gained entrance; my body shook, struggling not to just take her. When I pulled back and pushed up, our pubic bones ground together, she moaned, “Oh that is so tender, it hurts.”
“No, keep going. It’s good. Make it hurt.”
Her tender, tight sheath began to suck. I held off for a couple of minutes and then admitted, “Your body is too good; I’m going to cum in you.”
“God yes, take me as hard as you want and fill my belly.”
I would tell you how her words affected me. I would tell you about the next unknown amount of time. But I can’t. I went insane; I don’t remember. I do remember my balls disappearing into my body as I grabbed her and rolled so I was on top. I remember fucking her fast and hard, and my life flowing out of my cock making a pool at the mouth of her cervix for it to nurse my cum. I remember kissing her, telling her what she and her body were doing to me. I sort of remember arching so all my weight was on her cunt and feeling my cock dance inside her, long after I had anything to give her. I don’t remember passing out on her but I had to have done that because I woke up on top of her with my cock still inside her magic tight sheath. The clock said 5:05 a.m. Carla was looking at me. She whispered, “Can we talk some?”
I kissed her and her pheromones captured my now youthful libido. My cock grew inside her and stretched her. I grabbed her hips and rolled her on top of me. She looked shocked but when she rocked her hips, her eyes almost closed.
“Yes, wonderful woman, talk to me while you sit there and use me for your pleasure.”
We both rode right on the edge of grabbing the other and going for our own selfish orgasm while she talked about the harsh realities of an over forty year old woman, “I had a thousand new wonderful feelings with you tonight. I’ve always believed such pleasure was possible because when I masturbate, I imagined most of what happened. I came sometimes when Harold took me in the mornings but the beauty was always killed when he demanded things from me in his drunken loud voice every night. My dreams for what you did to me last night, I thought died a dozen years ago.”
“Not what I did to you, what we did together. Your body swept me away. My mind has always been with me until last night. Desire for you took my mind last night. You are wonderful.”
My lover was rocking slowly. I was quiet and she used me, just like I had asked. I watched as she learned to move. Harold must have never let her be on top. Beauty makes me cry. As Carla discovered her body and the pleasure it could give her, her fingers twisted into the hair on my chest, two of her nails dug into my nipples. Her hips kept experimenting. She finally found an angle that raked her clit along my cock, pressed my helmet into her magic spot on her down stroke and let her suck me as she pulled back. For minutes she did not change a thing. I could have lasted a month looking at the sparkle from her eyes in the dim light. Her eyes closed and her face contorted. Her fist tightened hard enough for her nails to draw blood and she climaxed using a man for her pleasure for the first time. We slept another hour or so. I dozed but was mostly embarrassed. Carla had become too important to me too fast. I was too old for her. For the moment I did not feel playful. I felt sad that I was not enough for her.
The room was dimly lit by the morning sun creeping through the almost closed black-out drapes. I slipped out of the bed and went to pee and wash up. I loved the smell of her that came back to life as warm water mixed with her dried juices on my body.
When I snuggled back into the bed and spooned against her, she woke up, tensed and had to go to use the bathroom. It was a good break. She remembered our night, our acceptance of each other and the best sex she had ever imagined. To my eyes, her body glowed around the thick flannel night gown, as she came toward me. Her expression darkened and she shuddered as her mind spoke harsh words, “He still has not seen your body.”
“Carla, stand right where you are.”
I opened the curtains another couple of inches, the room flooded with light. “You are the most wonderful, captivating woman I have ever known but I see worry in your eyes. Let’s get one issue out of the way. Take off your nightie.”
Tears rolled down her face but she lifted the thick, cotton garment over her head, dropped her arms, stood in front of me nude and defeated. I already cared too much; I cried. I reached for her and kissed every inch of her breasts, her chest, her belly, then moved to make love to her face and lips. This time she had my tears dropping onto her face. I could not speak. I knew she wanted me to say something but my mind was too full of sorrow. Her ex had obviously broken a bottle, pressed the jagged round opening into her left breast and drug it toward her stomach. Half her nipple was gone and the scars were shiny and sunken. He had thrust it twice more, twisted and jerked it across her. Once over her right ovary and then almost touching the same wound going for her pussy but hit right above it.
My voice was still locked up when she bowed her head and said, “My body is hideous, I know.”
Now my voice worked with my flowing tears, “No wonderful lady, you and your body are beautiful. I’m so sorry that some drunken, crazy man hurt you like this but it does not make you ugly. To me you are the most wonderful woman I’ve known. I’ve flirted with you for years. Now that I know you more, I have to confess that I’m falling in love with you. I know I’m too old for you and I know you travel most of the time, meeting far more desirable men than me. But take my words to heart, you are a beautiful, desirable woman, your scars are on your body, but they don’t detract from your inside or outside beauty at all.” I paused, “And…you are one hell of a lover.”
We had room service for breakfast, lunch and dinner. We both called in for a day off. Totally nude, she accepted my aging body and I accepted hers. The next morning, we skipped breakfast but early in the morning Carla wanted some attention. My parts were still sleeping. She had never kissed my cock but I woke up to her sucking me. Her eyes were frightened. I pulled her to me.
“What a wonderful way for you to wake me up. But you don’t look like you want to be doing that. How about a shower and let me get my hands on your body?”
Her voice was stern and distant, “No, I want to do this, I have to know.”
Yet another secret kept me from relaxing and enjoying at first, but a willing woman’s lips will always win over a dick. She was not very good. I was surprised. I told her a few things I liked and she was quickly quite talented. She learned how to torture me and slow me down, finally there was nothing either of us could do, “I’m going to cum, Carla.” I laid a napkin next to her in case she did not want to take me in her mouth. My first rope laced the back of her throat. She surprised me when I felt her tongue mash my cock to pump my second pulse directly into her stomach. She had almost fucked me dry during the last two days. I felt her swallow when my last meager offering bubbled from the tip of my cock. She pulled at my softening tube, licked my cum, savored it and swallowed again. Her eyes were teary.
Minutes passed and I spoke, “That was wonderful, my Beauty. Thank you. I saw your eyes, so I know that was not your favorite thing. Your gift of doing it anyway made it special. Watching you taste me and watching your throat muscles contract as you swallowed my cum into your belly made me love you even more.” Carla had never responded to my confessions of love. That did not hurt me; it made me sad. We were far apart in many ways.
She lay quietly on my belly with my cock touching her lips after my words. I wondered if she had even heard them.
“Harold held my head and pushed into my throat until I gagged. He called me horrible names when he was drunk and made me to do that. This is the first time I’ve wanted to have a man in my mouth. I enjoyed feeling my power over you and giving you pleasure. Your cum is salty and smooth. Harold’s was bitter and lumpy. I liked doing that for you.”
“I’m in real trouble now. You have kept me hard, wanting you and making love with you until my cock is almost dead. Now you have discovered how to bring it back to life even when I think it is an impossible task.”
She smiled at me.
Over breakfast delivered to the room, we talked about many things but little was about sex. Toward the end of breakfast, right before shower time, she blushed and said, “Remember the other night when you kissed … my bottom? I liked that, is that horrible of me?”
“No, I liked it too. How about when you were having trouble cuming and I pushed two fingers up your pretty ass and you came screaming and fainted. Was that OK?”
“My God, I was afraid to mention that. I’ve never had anyone play with me back there.”
“Let’s shower and get ready for a late lunch. There are some serious things I want to get off my chest and talk to you about.”
While Carla got our shower going, I dug in my shaving kit and found some Neosporin, it was the closest thing I had to a waterproof lube. I washed and fingered Carla’s ass in the shower. I had her work her clit. We were playing like kids with breaks for me to kiss her, suck her nipples and lick her clit. She worked on jacking me off with mounds of body wash lather. She had learned to twist her hands in opposite directions around the corona, make me moan and make me beg her to stop before I came way too quickly.
The shower had a built in bench. I had her put both her hands on it and I spread her ass cheeks and knelt behind her. With lube on my fingers I started kissing her tight ring and pushing my tongue at it. Carla had put her right fingers back to work on her clit, trying to match the movements of my tongue. I replaced my tongue with two fingers. She could match my thrust more easily with her fingers. She was moaning when she realized I had stood up behind her.
“Keep doing what you are doing. Stay relaxed and do what I tell you.”
I waited, still fingering her until her fear gave way to the routine she was used to. Her moans returned and I could feel her ass beginning to suck my fingers. I pulled out my fingers and touched my now well lubed cock to her slightly gaping ass hole. She wanted my fingers back so she pushed. I had stretched her enough that with a little push of my own, the helmet of my cock slid past her first sphincter muscle. It stretched her, hurt her, but now the big bell was past the constriction. She realized my cock was inside her ass. Her fingers had stopped on her clit but when they started again she rocked her body pushing slightly at the thick invader spreading her open.
My cock is widest in the middle. Every few strokes, Carla would stop waiting for the pleasurable stretching pain to subside as she adjusted to my thickness. I spent my time playing with whatever I could reach – her breasts, pushing fingers into her mouth to suck, rubbing her ass cheeks, rubbing over her ovaries and touching inside her thighs stretching open her pussy’s lips. Each round of this she would push back and more of my cock would slide in and she would groan. Finally she had my thickness. She seemed to know that. Her next thrust back was hard and long. I had her cheeks spread and she took me as deep into her bowels as possible. My short pubic hair nestled against her stretched ass hole and my balls swung into her clit. Carla gasped, “O My God.”
“I’m going to fuck you slowly until you are stretched enough for me to fuck you hard and fast. Keep working your clit in time with me. When I fill your bowels deep for the first time, I want you to cum with me.”
We had a slow build up. She learned fast as my thrusts jarred into her ass cheeks. We slowed again and mixed our pace easily and naturally. She seemed to know what I was going to do before I did. As she got close she matched thrusting back with my thrusts. I added a new component, I talked dirty, filthy and demandingly.
“Your ass has to be the tightest ass in the world. It is stretching my foreskin so tight I think you are ripping it off. Yes, suck me with your ass. I’m going to cum into you so hard you will taste my cum in the back of your throat. But that’s what you want isn’t it. Squeeze your ass muscles and feel me pull out and thrust back, stretching my way into your ass.” On and on I went. Her breath began to match the beat of my words. Her ass began to suck and my I.Q. was quickly approaching zero. Without much warning I said, “I’m going to cum” and roared like a lion lifting her off the ground with my cock burying it even deeper into her as it danced and emptied in her. Her own fingers pushed into her cunt and felt my dancing cock. She cried out and came with me. One, two, three and then some tremors of a pulse was all I could take before my legs felt weak.
I managed to turn her and sit on the bench and pull her down to sit, impaled on my throbbing satisfied cock. She tilted her head back to one side and we kissed while I held her breasts until my cock softened and slipped out of her ass. She felt my cum trickle out of her. She touched it. Looked at it. Rubbed it onto her lips and tongue, then giggled like a naughty little girl. I think at that moment she became complete jumping from a naughty little girl, to a curious teenager to a complete confident sexual woman.
The horrors could still be conjured up but now she had good memories to balance against those horrors. Strangely, this allowed Carla to transcend from stage to stage leaving the ugly memories behind. For that moment, at least one man did not see her scars, so she did not see them either.
It was time to get washed up and out of the shower but neither of us knew what to say or how to stop our morning adventure. I’m always the silly one, “Did I just take your virginity?”
“Yes, you naughty talking man and I loved every second of it.”
Carla had just divulged more about her new self than she would understand for months. I knew I wanted her to be mine but I never wanted to hurt her, disappoint her or for her to be sad that she had missed something by settling for an older man.