January

January is a very special woman. At least, I think so, and I doubt I am the only one. She is smart, outgoing, kind, and heart-stoppingly beautiful. I have had a crush on her for longer than we have been friends, and I have been her friend long enough that I can talk with her and not get tongue-tied and keep the more obvious physical manifestations of my feelings for her under control, but I am sure she suspects something. It may be that she has the impression that I call all my female friends "Beautiful" and ''Sweetheart.'' Perhaps it is best that she think that; she hasn't asked, and I am certainly not going to volunteer the truth.

We were meeting for a drink; we hadn't seen each other for quite a few months, and we had each started new jobs recently, so it was time to catch up. We sat together at a lovely neighbourhood bar and chatted for hours. I don't think either of us stopped smiling for the whole time, and we couldn't keep our eyes off each other! Our conversation went in all directions, covering our previous jobs, our new jobs, the weather, friends in common, family and acquaintances. I think I could listen to her talk for hours, but she is so gentle and graceful that I always feel like a frog-voiced brute in her presence.

Finally, she looked at her watch. This was the minute I had been dreading, but I knew it was coming. We would say good-bye, and not meet again for a few months. I'd been through this before, and was used to it, but it was never easy. I took a breath, and steeled myself.

Her next words surprised me.

"You have a crush on me."

It was very matter-of-fact. It was tough to tell whether she felt flattered or offended, but it was clear she had known for a very long time. I looked back into her beautiful eyes. There didn't seem to be much to say to that, so I just nodded and smiled.

"I'm glad to see that my statement doesn't make you panic. I really like you too. And I can sense how much you want me every time we're together. I know exactly how you feel, but I've been burnt before, so I now have some tests I put men through before I'll consider dating them. They will make sure that we're compatible, that you trust me, and that you are as open-minded as I am. If you pass the tests, we can do everything you've ever wanted to do. If you don't, we stay as friends, if you're comfortable with that. Some of the tests are very intimate and one-sided, and most guys who don't make it can't look me in the eye again afterwards. I have to admit I've been evaluating you over the past few years to gauge how you'll manage, and I have high hopes that you'll do just fine."

I couldn't say no, naturally.

"I'm in. When do we start? Just tell me what to do."

"Follow me."

I went with her. My car was parked two minutes away, with a meter which was going to expire in twenty minutes, but a parking ticket or towing fee seemed like a small price to pay. We headed up the hill to side street where she was parked. She opened the door for me, and I got in. She drove to a nearby plaza, and parked just on front of the drug store. Rush hour was almost over, and traffic was light.

"Here's your first mission. Go in there and buy both an enema and condoms. Unlubricated condoms, without any spermicide. The brand doesn't matter. Bring back the receipt, so I can make sure you bought them at the same time from the same sales clerk."

That really didn't sound so hard. I could see some guys being a little embarrassed by purchasing one, the other, or both, but I had no problem with it. I found them easily, and was back in her car within four minutes brandishing the receipt. She gave it a quick look, and said "good" just loud enough that I could hear it.

We went on to her place. "We're here. Don't forget your purchases," she said. I got out of the car and followed her inside. As soon as we got inside her door, she said, "strip." I knew she had a roommate - in fact, I had known her roommate longer than I had known her, but she had told me that this was a trust exercise. If her roommate saw me, either she was in on it, which was cool with me, or January would have some explaining to do, which was also not going to worry me. I have nothing to be ashamed of in that department. I undressed completely without hesitation.

She looked at me, and smiled. "Your are already doing better than most. Follow me."

She led me to the bathroom, and put a towel down on the floor. "Supine," she commanded, and I lay down. She picked up the enema bottle. "Lift your legs in the air. I'm going to administer this. You have to be very clean for the next part of the test. Now relax." This was a new experience for me, but it was far from unpleasant. I felt as if I was her pet, her property, her plaything, and I loved it. I made myself breathe normally, and forced my buttocks to relax. I felt a slight pushing where things don't normally push, then a sensation of fullness, and finally, a withdrawal. I looked up at January. She was looking at her watch.

"Now just lie there until you need to get up. Let's try to keep that in for ten minutes. Don't worry, this isn't part of the test; when it hits you, you can't fight it, and if I have to clean my towel or the floor, we're done here."

She smiled as she said it, but I certainly didn't want any accidents on my watch any more than she did. I lay there, more vulnerable than I had ever felt in my life, while she stood over me counting the minutes. Just after she reached seven, I felt incipient uncontrollable spasms. "It's time," I said, and got up.

"You have five minutes to finish your business and clean yourself up. If you take a shower, you'll have to use my towel."

She checked her watch once more and left the room, leaving the door open. Fortunately, nature took its course very quickly, and I was out of the shower and drying off well before she came back in to say "Time's up. You're still in the game. Now onto the next mission."

I followed her mutely into her bedroom.

"Shut your eyes. I have a surprise for you."

I closed my eyes, but listened intently. I could hear her walk away from me, over to the wall. A drawer opened and closed, and then another. I could hear rustling, and was sure she was removing her jeans. I could feel myself starting to get hard at the idea. Apparently, she was still watching me.

"Oho, so you like what you hear, do you? I hope you like the surprise that goes with it!"

I kept my eyes shut, trying to decipher what I was hearing, but it was too quiet. Finally, I heard her giggle.

"Now we'll see what kind of man you are. Open your eyes and look at me."

I turned my head to face her. She was wearing skin-tight black tights and, strapped around her waist, was a harness holding a good-sized dildo. On some women, this would have looked scary or lame, but on her, it was incredibly sexy and exciting. I could not hide how I felt about seeing her like that. She went over and sat on the bed. Reaching behind herself, she grabbed a pillow and dropped it on the floor on front of her.

"Get on your knees and show me what you would like me to do to you."

As I bounded across the room and knelt down before her, I saw her look at her watch again. I'd never done anything like this before, and I think she knew it, but by now, we were both fairly confident I would enjoy myself.

I leaned towards it, and kissed the tip, shyly. Then I ran my tongue around it, and up and down. I was more excited than I thought I should be, but realized quickly that I was more open-minded than I had given myself credit for being. I spent a few more minutes kissing and licking it before deciding to take the plunge. I put both my lips around it, and, gently at first, lowered my head towards her body. It felt completely natural, both physically and emotionally. I felt an almost unbearable strength in my own manhood as I took her into my mouth. Up and down I rocked, resting my hands on her thighs and moving only my neck. Soon, to my great embarrassment, I could feel my saliva flowing towards her. I was drooling like a baby. I slid my hands in and circled the base of her shaft with my fingers. I tightened my lips around her, and started moving more rapidly. It felt great to be so aggressive. I slowed down for a few seconds to see how far I could go without gagging. I think I did okay, but I would have to go home and buy a one of these of my own to practise on. I knew I could do better.

I looked up at her, and winked. She was grinning ear to ear. I kept at it, and finally she said,

"Okay, Killer, that's enough. Outstanding job. You're quite the little cock slut, aren't you?"

She said it with affection, and even a little surprise and respect.

"I never really thought of myself that way, but I suppose, at least if you're involved, I am!"

She was still smiling.

"So am I, as I hope you get the chance to find out. We have two more tasks to go. They are both very important. The next one is likely to be a little painful at first, but I really, really hope you like it."

I smiled, maybe a little weakly. I had a pretty good idea of what was coming my way. I tried to speak confidently.

"Where do you want me?"

"Sit at the edge of the bed facing me, then lie back. I think you've figured out where this is going, so I am not going to explain it too much. I am going to use plenty of lube, and I will be very gentle, at least to start. Do yourself a favour, and try to breathe normally. If you hold your breath, it will hurt more. And try to keep those lovely blue eyes of yours open. I really to want to be able to see them while I'm doing you."

I sat on the bed as she asked, and lay back. My legs were hanging a little awkwardly over the edge; I was curious to see the logistics. I looked over at her. She had put one of the condoms on her now somewhat intimidating prosthesis and, true to her word, she was applying a generous helping of a shiny clear gel.

Then she stepped over to me, holding a towel in her left hand.

"Spread your legs, and put them on my shoulders."

I complied, smiling. I was starting to get excited at the prospect of her taking me. I had never experienced this before, and was looking forward to it.

"Oh, and put on one of the condoms. Just in case."

It felt strange knowing that she was watching me from between my legs and above, but I was certainly hard enough that it went on easily. After I had finished, she reached down to my backside, and I felt her rub a substantial amount of her gel around, on, and even a little inside the entrance to my unexplored depths. I took a deep breath, and then another.

Again I felt some pushing, and then the completely new and most definitely pleasant sensation of being penetrated by someone. It was indescribably erotic and intimate. I felt movement, and more pushing. It was quite comfortable, really. I looked at her. She was not as close to me as I had expected; my legs were still braced on her shoulders, but her body was over a foot away from me. I realized she was softening me up, as it were, with her fingers. I guess this would ease her entry when the time came.

I felt a third finger come into me. This was starting to stretch things a little. It wasn't painful, but it also wasn't entirely pleasant. I forced myself to smile, and kept my eyes on her beautiful face for comfort. I saw an intense combination of compassion, lust, and determination in her look. Knowing her history as a runner of many marathons, I recognized clear as day that there would be no turning back for either of us. I took another deep breath to relax myself as her fingers withdraw. I felt her wipe her hand on her towel as she stepped forward, closing the last few inches between us. I felt the hardness of her substitute manhood against me, and then a very quick push, and she was inside me. Remembering her advice, I kept breathing. It hurt, more than I had expected it to, but it was also novel and exciting. I could see that this would always be exciting with her, even if it stopped being novel. She pushed herself further into me, and further. As she had promised, she was very gentle with me. She stayed still for a few seconds, to let me get used to all the new sensations streaming though me.

She pulled back a little, and then pushed in again. She repeated the action, with less of a pause and with a little more speed. Again and again she thrust into me, and each time it felt better. She kept up a relatively easy pace, no doubt so she wouldn't tire herself out. My pulse was racing with excitement, and I felt out of breath, but I forced myself to relax. I was really starting to enjoy this.

I lost complete track of how long we spent like this, but eventually, she quickened her pace. I felt a powerful excitement flood through me, and I was soon quivering a little with every thrust. Finally, when I felt I couldn't take any more of this incredible pleasure, I felt myself caught in a powerful quake of pleasure. I gasped, moaned, and almost screamed at the same time as I spasmed in the most intense explosion of sexual energy I had ever experienced. I felt exhausted, physically, mentally, and emotionally. She pulled out, completely this time, and stepped back.

"That was amazing, and wonderful, just like you. Thank you."

She smiled at my words as she removed the harness and put it down.

"That was fun. I enjoyed it myself. You know there's one more part to the test?"

"I remember. I can't wait to find out what it is."

I looked at her expectantly.

She sat on the bed beside me, and reached towards my crotch. Careful not to spill a drop of my essence, she peeled the condom off me. I was still lying down, watching her. She put the open end to my lips. Holding it around my lips with one hand, she pushed it into my mouth with the other. I was tired no, too tired to find this titillating, but it would be a disappointment for both of us if I were to falter here. It wasn't, couldn't be, more than a few drops. I felt it fall onto the back of my tongue, and decided to take a little more charge of it. My tongue circled her finger nestled in the condom, and then I took her other hand in mind and slowly pulled the condom out of my mouth, trying to clean with my lips. Once it was almost out, I pushed it slowly back in again, more in an attempt to retain her interest than because I felt it needed a second run. This time, I pulled it out all the way. It was completely clean.

She was glowing with pleasure, and maybe some pride.

"Congratulations, you passed all the tests with flying colours. We are going to have some very fun times together."

I knew she was right.