The Game: Second Date

"The Game," wasn't really a game but more of a sexual dating adventure. During my third year at college I met a stunning young woman named Michelle. We were soul mates, partners on a different level than most, and we shared a great deal with each other including the desire to remain physically free in our relationship. We both enjoyed the pleasures of the flesh too much to limit ourselves at that age. It was Michelle who first conceived the details and eventually devised this plan to sate our physical appetites.

Michelle had been bragging to her friends about how good I was in the sack, how versatile and varied my style could be, and she found a few women who wanted to be "set up" with me for a "date." These dates were to be conducted anonymously, with the end of the evening predetermined, a cross between a blind date and a one-night stand. We had a code word to stop the action and a level from 1 to 5 of the kind of activity the lady wanted, 1 being a gentle prolonged affair and 5 being nearly a rape fantasy. I would identify her in a bar by a specific pin she wore, a red, white and blue airplane, pinned to her red blouse or sweater.

My first date had been a rousing success. Michelle had sent me a voluptuous young lass with an appetite for excitement and I had started off with a level 4 adventure. She was a hot one and the sex that night had been incredible. We had even dated briefly after that night but Michelle exercised her rights to keep my penis under her control and made us quit. It's just as well because the girl was as stupid as she was hot.

A few weeks after that first encounter Michelle told me about another willing participant who wanted to sample my services. I was excited about it and readily agreed to meet the girl the following evening. So far Michelle was fabulous at choosing women for me and I was sure she was right when she told me I would enjoy this one.

The next evening I went to our designated bar a couple of blocks from my apartment. The Ugly Mug was a little hole-in-the-wall kind of place frequented by townies and most of the crush of alcoholic college kids avoided it. It was long, narrow and dim and it was usually quiet for a bar. I arrived early and took up my normal spot at the far end of the bar where I could see the entire place and everyone in it. I ordered some Irish coffee to keep me company and waited for my date to arrive.

She was a little late and I was on my second cup. I could tell she was a red head and of medium height right away, but the rest would have to wait until she came closer. She moved with a purpose and scanned the bar quickly. There was enough of a Friday night crowd present that I thought I could remain anonymous for a short time, but as soon as she saw me she came right for me. I found out in a moment why.

"Becka?"

"Hi there. You remembered!" She said brightly as she gave me a hug. Becka was Michelle's old roommate from last year. I had met her once or twice but we hadn't really interacted much. Becka was about 5' 5" and nicely built, though there was nothing really special about her. She was pretty in a way, but again, nothing special. Her eyes were a little small and high on her face and her nose was long and slender, but certainly not freakishly so. I have a soft spot for women who look unique and Becka certainly did. She just had a way of looking odd and I never could quite figure out why. Her red hair was short and curly, and for a moment I pondered that I seem to have had more than my fair share of redheads in my life. But those are other stories.

"This is a little strange. I've never done this with someone I knew before."

"Don't sweat it. Michelle said you could roll with the punches." She giggled a little at that. "Besides, I already know I like you so you don't have to worry about that. I don't know if you like me, but that's your job tonight, right?"

"Kind of, sure." I replied. "We are here for a mutual arrangement, so it's not quite like I'm your personal love slave for the evening. By the way, do you have the pin?"

"Oh, yeah," She dug in a pocket and showed me the pin, a red white and blue sparkly airplane I had given Michelle several months ago. She put it back in her pocket. Her movements were quick and jerky, almost clumsy, as if she were drunk or nervous.

"Listen, do we have to do the whole 'word and number' thing? I just want to talk to you about what I want and then go do it, OK? I'm not good with the whole role playing thing."

"No problem," I replied. I was flexible for a good lay.

"Great. I don't drink and the smoke in this place is killing me so can we go back to your place right now?" She was bouncing up and down on her toes and seemed now more worked up and nervous than before. I quickly agreed, dropped my payment on the bar and followed her bouncy steps out.

The apartment building was within stumbling distance of the Mug so it didn't take long. On the short walk she remained jittery and tense. Her fidgeting hands were in constant motion but she said little. Once at the apartment I let her in and closed the door behind us. My roommate spent most of his time at his girlfriend's apartment so I didn't have to worry about him.

Once inside she moved around the apartment, snooping lightly and commenting on the place. I sat down at our little kitchen table and invited her to do the same. She flopped down in the chair, hands still fidgeting wildly. She must have been nervous. I held out my hand on the table and she looked at it for a moment before she jerkily put one of her slender hands in mine.

"Listen, there is no need to be nervous. I will respond to whatever you want and I'll stop at a word." I bent down to kiss her trembling hand. "You need have no fear of me."

"I'm not afraid. It's just been a long time. I'm excited. Plus I've never really, you know, started a date like this. The guy usually makes all the moves."

"I understand. Do you want me to go ahead and make the moves?"

"Yeah, that'd be great." She seemed to relax a little at that, though I could still feel the shaking through her clammy hand. "Just, no rough stuff."

"No rough stuff. I think I'll give you the luxury treatment." I leaned over and kissed her hand again, then stood and moved around to stand beside her. I gently pulled her up from her seat and she stood in front of me. I released her hand and put my arms around her slowly as her shaking increased again. I hugged her firmly to me and held her. For a moment she didn't know what to do with her hands, but she soon put them around me.

"Just relax. Get used to my presence. Stop me at any time." I started rubbing her back a little, just turning my hand at the wrist. Her shivers slowly receded and she started to nestle into me a little, breathing deeply of my scent. Michelle always told me I smelled wonderful and I hoped Becka felt the same way.

We stood there for a few minutes getting used to each other and when I thought she was ready I let her go and leaned back a little to face her. Her strangely pretty face smiled up at me and she touched my face with a brief, friendly gesture. I echoed her gesture, but let my fingers slowly trace down the side of her face and cheek, brushing her hairline and ear. As my fingertips reached the bottom of her ear I moved my hand back behind her head, fingers splaying through her hair, and slowly pulled her face to mine, tilting it back slightly. With my other hand around her back I pressed her against me as our lips met and I gave her my very best first kiss.

Our lips met first, a light touch but very strong with anticipation. That kiss was swift and quickly broken, but I moved in again with a little more contact and a little more force, still gentle and calm. Again the kiss broke, and again I moved back in, this time flickering my tongue against her lips. Her tongue shot out to meet mine this time and the kiss lasted much longer. She was a good kisser and her sharp little tongue tasted sweet and lovely.

We kissed for several minutes, holding each other tenderly and taking it slow. I took my hand out of her hair and caressed her face again, then ran my fingers down her neck and to the border between skin and blouse. Her shuddering had subsided during the kiss but she jumped a little as my hand neared her breasts. I broke our kiss and looked her in the eye.

"Are you ready to go into the bedroom?"

"Yes. I'm ready."

I released the embrace but continued to hold her hand, leading her down the hallway to my room. She trailed along quietly and I could feel her hand becoming clammy again. My room was small but cozy and I had cleaned up before I left so it was very presentable. I entered first and led her in, then closed the door behind her. She turned to face me and I took control of the situation.

"Turn around and face that mirror over there." I had a floor-length mirror propped up on the floor on the wall and she stood so that she could see herself in it. I moved behind her and placed my hands on her hips after I moved her medium length red hair from her right shoulder. I leaned down and kissed the base of her neck, gently nibbling up to her ear. Once there I nipped at her earlobe with my lips and she leaned into me a little.

"Just stop me if I go too far, OK?" She nodded mutely and I moved on. My hands rose to the top of her blouse and I started undoing buttons. The top one was easy, the second one stuck a little but that allowed my arms to brush her breasts through the thin red cotton. Her breasts were nicely formed and medium sized, perfect for her frame. The rest of the buttons went easily and in a few moments the blouse was open. I worked it up out of her waistband and pulled it open and down over her shoulders.

She wore a sensible white bra and I was delighted to see that it opened in the front. I love front-loaders. I raised my hands to her throat and ran my fingers down across her collarbones, down toward her breasts, then out and around them. I caressed the sides of her breasts through the soft material and moved down her torso until I reached her blue jeans. I undid the button and unzipped the fly, but then left them alone.

My hands now went to the clasp and I deftly undid her bra. I moved the fabric away and bared her pale, pretty breasts to the room. Becka was leaning back into me now and seemed considerably less excitable than she had before.

Before touching her bare breasts I pulled her shirt and bra off her arms, leaving her naked from the waist up. I will admit to a bit of a fetish here. There is something delightful about a woman who is topless and wearing unzipped blue jeans. It is sexy, beautiful, suggestive, and utterly erotic to me. The quickest way to my heart is for a woman to pose like that for me. My erection grew quickly at the sight of her perky young tits and pale freckled flesh. Her nipples were barely darker than the rest of her skin and they looked soft.

I moved back in and put my hands at her sides, just under her breasts. I moved them forward until they were fully underneath, then gently moved them up and pulled her back into me. She gasped a little as I held her to me, my hands full of her soft, sensitive flesh.

I continued nibbling at her neck as I held her breasts. My tongue flickered at the base of her neck, moving up to her ear as my hands slowly caressed her skin. My fingers moved lightly over her pink nipples, turning them darker and harder very quickly. Her hands came up to mine and I let her direct me for a while. I continued working her neck and ear as her pulse quickened.

My left hand moved away from her breast and down her flat belly. I slipped a finger into her panty waistband and pushed in just enough to brush her pubic hair. She shuddered against me and closed her eyes as the lust began to grow inside her. My right hand gently cupped and caressed her breasts as my left moved back and forth across the top of her panties.

I have learned over time that sudden escalations are often powerful tools and I decided it was time for one. I brought my left hand back up to her neglected breast and fondled it lovingly for a few moments, then made my move. I moved both hands down her torso, pushing her into me as they fell below her tender breasts. I continued down swiftly, my fingertips reaching the waistband of her panties and plunging under. I pressed my hands down into her white cotton underwear, pushing the fronts of her hips back into me and grinding my hips into her backside. She gasped at the intrusion into her pants, excited and thrilled at my hands so close to her delicate womanhood. I held her there for a moment and enjoyed the sensation. Her hands pressed mine through the denim, holding me there as she reveled in the feeling.

It was time to get her out of her jeans. I brought my hands back up to her breasts and pulled her snugly into me, biting her neck a little where she seemed to like it best. Then I began to slide down behind her, dragging my hands down her front and my tongue down her back. As my hands reached her pants I pulled them down, my face now at the small of her back. I began to kiss her just above the panty line as her denim slipped over her hips. She kicked out of her shoes and allowed me to pull the jeans off her feet until she stood there, topless, wearing only panties and socks.

I stood up slowly, bringing my hands from her ankles, up her calves, forward to her thighs, up the front of her hips with my thumbs and forefingers brushing her tender region as they passed, up her belly, and as I stood up entirely my hands went to her sides and under her arms. I raised her arms with my hands until they stood high toward the ceiling, then bent them at the elbows so she reached behind her and touched my head. I held her elbows, then brought my hands slowly down her arms and breasts, down to her panties where I pushed the waistband down a little, then back up, all the while nibbling and sucking at her neck.

I worked her panties slowly downward, rolling the left side a little bit, then the right, caressing them off her slender thighs. Once I had them as low as I could reach, halfway down her hips and exposing most of her bush, I hooked a finger into each side and bent down, pulling them quickly to the floor.

Becka was very excited at this point and as I stood back up behind her she turned to face me. Her hands went to my collar and started undoing the buttons, but they trembled terribly. Her breathing was quick now and she wanted to get my clothes off in a hurry. I let her undress me at her pace, and in a few moments she was tugging down my blue jeans, exposing my boxers and the bulge within.

As she pulled my pants to the floor she remained on her knees in front of me and reached up for my cock. As badly as I wanted to let her continue, I had a plan in mind that I wanted to put in place first. I intercepted her hands with mine and pulled her up to her feet.

"Not yet. Maybe later. I have more for you first."

She smiled that odd, quirky smile of hers and ran her fingers through my chest hair.

"What should I do, then?"

"Lie down on the bed and get comfortable. On your belly, please." Again she smiled, and as she moved away from me she let her fingers brush against the swelling in my shorts. Her touch was a jolt to my system but I had to remain calm. This might take a little while.

She crawled on the bed, making sure to give me a nice view of her ass, and dropped down on her front, legs slightly apart. She grabbed a pillow and folded it under her chest to prop her up a bit. Her initial hesitation seemed to have fled and she was into the swing of things now. Perhaps she no longer needed the pampering I had in store, but I decided to go ahead anyway. I hoped she would appreciate it, as I desperately wanted the blowjob I had turned down moments before.

I had a few items in my nightstand I kept for intimate occasions and I retrieved a bottle of massage oil from it this time. I poured some on my hands as I sat next to her naked body on the bed. With thoroughly oiled hands I started rubbing her back, widely at first, working the lotion around to cover her soft skin. She purred a little and snuggled into the pillow in appreciation.

After her back was well oiled I started working methodically down her spine. I started at the base of her skull, gently kneading the top of her neck and the hairline and pulling my fingers slowly down. At the base of her neck I moved out and pressed my hands firmly against her shoulders, then continued massaging down her arms to her elbows. Moving back to her shoulders, I started pushing with some force against her shoulder blades, eliciting a gentle groan.

I continued moving down, giving her the best sensual massage I could muster, somewhere between a relaxing muscle rubdown and a fingertip brushing. As I reached the top of her ass I lifted a hand and gave her a bit of excitement. Placing a fingertip at the top of her back I slowly moved it straight down her spine and into her crack, almost down to her most tender area. As I reached the end of the finger's journey she squirmed considerably, showing me that I had done it correctly.

I worked her glutes well and tenderly after replenishing my oil. I avoided probing her and concentrated on the skin and muscle below, making sure the relaxation was the priority and not the titillation. I knew how excited she was and I wanted to make sure that when this moved on to the next step it would be a flawless transition.

I worked my hands down her legs, making long slow movements up to her waist and down to her calves. Now it was time to start moving closer to the final destination. As my hands moved up her legs I began brushing my fingertips nearer her nether regions. Always gently, and never poking or prodding, I massaged less of her legs and more of her upper thighs and ass. She moved her legs wider to give me better access, and now it was nearly time to touch the fire I had been stoking.

I moved a hand all the way up her inner thigh, finally reaching the prize. She gasped as my hand touched her pussy. She was very well lubricated and there was no resistance to my thumb as I slowly inserted it. She wiggled a little on it, trying to push down harder, but I moved it slowly back out and gently worked it around. I kept it shallow and slow, sexy and provocative, rather than a pummeling. That might happen later, but it wouldn't be with my thumb.

My left hand continued to roam around her back and legs, but more often now it returned to her buttocks for a stronger massage and a little exploration. With each trip near her back door with my fingertips I pushed my thumb in deeper, hoping to have her equate good feelings with my attentions toward her ass. I didn't expect the night to go that route, but a little preparation never hurts.

She was starting to get very squirmy and wiggly on my thumb so I decided it was time to escalate. She was ready, I was beyond ready, and this teasing business had gone on long enough. I pulled her up at the hips, indicating that she should get on her knees. This she did, pointing her ass up in the air expectantly. I whipped off my boxers, crawled on the bed and got on my knees behind her, my erection poised to enter her.

I grabbed my dick and moved the head to her eager beaver, pushing it in just enough to become well coated with her fluids. I moved my dick up her crack, over and past her anus, up to the top of her ass, then back down. I pushed forward to her clit and wiggled my dick against it, eliciting another groan from the poor girl. She was trembling again, but in anticipation this time.

I repeated my maneuver several more times, wiggling and pressing my slimy cock head against her clit, pussy and ass, working her up to a frenzy. Her fists clenched in the sheets and her head thrashed every time I brushed her clit. She tried to push back against me as I passed her pussy lips but I held her back with my hand on her hip. It was time.