I'm a past-middle age divorced female who has enjoyed several strictly on-line sexual relationships. A male friend from on-line was having a bad day and needed some inspiration. So I wrote this fantasy story and sent it to him. That was several years ago, and I’m not in touch with him anymore so I thought it would be okay to share it with you.

My most favorite real-life experience was with a very kind and gentle man who took his time not only during on-line sex chats - when we both masturbated - but he took his time and was very gentle during our one and only real-life session. Prior to our encounter, we chatted for weeks on-line. There was a lot of discussion about the kinds of things we wanted to do together, make love outside, in the shower, and of course anal sex.

I was not experienced with anal sex, but I was curious why so many people on-line thought it was so great. I had tried it once with my ex-husband, and once with a boyfriend before my marriage. But both times it hurt too much to try it again. I had privately masturbated thinking about anal sex. And, I had tried inserting my finger or occasionally, I had experimented with an object. And, I can remember as a little girl being fascinated with the idea of inserting things into people, like a doctor or nurse putting a thermometer in someone's bottom. My on-line lover claimed to have a lot of experience with women and anal sex, and I believed and trusted him.

When we were finally together, it was terribly exciting. The anticipation was more than either of us wanted to admit. We had talked about so many different positions and things to try, but we knew we couldn't fulfill everything we dreamed of in one afternoon session (at least not at our age). We made love the conventional way so he had climaxed once.

We were in bed spooning, resting in our afterglow. I was lying on my left side and he was on his left side, snuggled up behind me. With his right hand, he reached over me to the nightstand for the lubricant. I was thinking - 'this must be it', my time has come to experience real anal sex. With his fingers he put some liquid all around on the outside of my hole, and then he applied the rest of the liquid from his hand on his soft penis. His touch on my anus made me very hot with anticipation, my mind was racing with a million thoughts. (What will he do next? A finger? Am I going to let him enter me there? I can always say I'm not ready to try this. Is it going to happen now, this instant, or will he take his time? Will it hurt and I'll want to stop? Is his penis coming into me now? Oh my gosh, is this it?) I squirmed and moaned - waiting - and almost wanting him to insert that finger - the one applying the lubricant.

But he was enjoying the tease, and he smiled. He wanted me to wait - and want. After all those on-line chats about anal sex, he knew I was ready to try it, that I really wanted the experience. He promised to go slow and stop if it hurt at all. He had assured me that if it is done right, entry and stroking should not hurt -ever- and should be enjoyable. He knew he was in charge of making this experiment a memorable and enjoyable experience for both of us. But he wanted to be sure I was ready. And, he wanted me to wait.

With his hand, he took his relaxed penis and rubbed the tip all around my opening until he had it perfectly positioned. And then he just stopped. He took his hand away from between us and pulled me close and began whispering to me. He said he wanted me to have control of the entry. He told me to take a deep breath and relax. He said it didn't matter how long this takes today. He said we should slow down and enjoy this together.

I was beginning to beg him, but could only say out loud "please". I was so hot - literally - with anticipation, I could feel my face flushing and my heart racing. I waited a moment, and he didn't move. So I begged again "oh please"? I wanted him to push it inside me. I had never wanted a man's penis so much in my life. I had never needed to ask a man to have sex with me - I was the kind of woman that always had a man available to her. So asking a man to 'please put it in me' was not a natural thing for me.

I closed my eyes so I could feel him and etch every single moment and sensation into my memory. He was so close behind me, cradling me, and whispering, talking to my mind, reassuring me. He was in complete control and I was begging in submission. He said . . ."Tell me exactly what you want. . .Tell Me".

In my entire life I had never been vocal during sex. I would never and couldn't possible say out loud what turned me on. With my ex-husband it was like an unspoken dance, through the years of sex we just knew what came next in our routine. But this was very different. This was our first time in person (not-on-line) so we didn't really have a routine.

And I had been without a partner for a long, long time. That fact, along with my age, gave me the courage to try to enjoy this, who I am sexually and what my needs are. Now I was 'in the zone' - it felt like I was on a drug and I could only think about getting something in my bottom - his finger, his penis - I didn't care which, I was just ready and wanting this to happen now, I just wanted to try it.

The silence in the room was obvious. I was fighting with myself to answer him and say something - something dirty, and at the same time the words in my mind seemed vulgar. I had typed words to him on-line. Why couldn't I just say them now out loud? All I wanted was for him to enter me and I was bargaining with myself to just say something.

Because he understood me so well and could read my mind, he helped me by saying the words for me. He said "Tell me you want your ass fucked. Tell me you need an ass fucking like never before". It was so easy for him, the words just hung in the air - echoing - and fully understood. Now I thought I could say it, I just needed to repeat his words and I said "Please" (again, and that was easy) - and finally I whispered the words "fuck my ass, . . . please?"

"That's my girl," he said.

"Now bear down". His command took my breath away. I thought it was nasty but erotic for him to say that - or for anyone to ever hear those words uttered; 'bear down.' But I knew that's what I needed to do to take him inside me. I needed to bear down just like with a bowel movement, or when the doctor does a rectal exam on me - and says, 'bear down,' and I am being commanded to open-up and accept the entry into my bottom.

My lover's hot whisper to me continued and he said "You have to show me you want it. YOU make it happen. You push it inside. It will go in when you're ready, just open up for me. Come on now, let's try this."

God, those words. Why did his words make me wild? Why was I needing him to talk to me, to guide me. Wasn't it enough that I needed to feel him inside me? Why was I cherishing his gentle encouragement and hanging on every word.

I didn't move - I was frozen. I was holding my breath in anticipation. Any second now and he would be inside me. A long moment of silence, and he continued saying, "Come on, breathe, we can do this. Let me inside you".

I was quiet and still.

"One more time I'll say it", and with a forceful tone he said "Bear Down".

That was it! - that was all I needed to hear. He was steady and strong holding his penis right there ready to enter. I turned my head and looked over my right shoulder into his face. We looked into each other's eyes as his penis broke through my bottom and filled me, and simultaneously, I could feel his erection returning to fullness. I let out a long slow moan of pleasure and pain. I turned my head back away from him and grabbed his right hand. I squeezed it hard - with the intensity of what I was feeling in my bottom.

I was thinking that at any moment it might hurt even more, and I was starting to be afraid. He sensed I was about to panic and he wrapped his right arm around me, across my chest, and held me very tight so I couldn't move.

He began whispering to soothe me

"Hold perfectly still" he said. "Try to relax your bottom and I promise NOT to move either. The pain will go away in a minute. Remember to breathe deep and slowly without moving. Concentrate on feeling me in your bottom - the good feeling - the fullness - you will get used to me."

After a minute or two he said "Just continue taking slow deep breaths and wait. It will happen, trust me. You will love this as much as I do."

And yes, just as he predicted, slowly, I began to relax and my body accepted him, and everything started to change.

It was a magnificent feeling. The best I had ever experienced, better than when I masturbated. He penis was warm and filling, a much better feeling than when I masturbated with a hard, cold object. I loved just knowing he was inside me. I have so many more feelings and sensations rectally than vaginally. I moaned a little with pleasure. As my bottom continued to open and co-operate he said, "I can feel your body changing. Are you ready?"

I could not speak but I moved my hips ever so slightly to acknowledge his question.

He began to move with a small, short stroke, and with each succeeding, it was more pleasurable than the last. He was not going in deep, and I was breathing normal again and attempted to follow his rhythm.

I let go of his hand, and then he tried to pull my hips closer to penetrate me deeper. With each insertion I exhaled and moaned a little louder. He stopped for a moment, holding perfectly still while inside me. I took a deep breath and held perfectly still too. He said "Bear down again." And as I did, more of him slipped deeper inside - until I could feel his hips pressed against my bottom and he was fully inserted. I exhaled knowing I'd been completely taken and this was the joy and passion I'd so longed to experience. Now the strokes were slow, full and complete. A wonderful experience - a dream that I never wanted to end.

This was pure bliss, utterly fantastic. I wanted all I could get and more. With my right hand, I reached back and pulled open my bottom cheek, trying to spread wide to allow closer and deeper access. He said, "Oh yes, you like this don't you?"

Then he stopped. He held perfectly still with his penis buried deep. And suddenly, without warning, he quickly withdrew all the way out. Then he waited - holding perfectly still again, for what seemed like forever. But this time the head of his penis was perched just outside my anus. And he made me wait, not knowing when - at what exact moment he would re-enter. I whimpered in a kind of begging - a wanting - wanting to be filled again. He was enjoying my torture.

Then suddenly he re-entered me again, with one full motion, burying himself deep inside me. Each single stroke brought more anticipation for the next. And with each movement of withdrawal, I wanted it reinserted - quickly - filling me again. But he was making me wait. It was a constant beg for both directions - I loved the feeling of withdrawal, yet I wanted to feel it re-inserted and filling me. And he was purposefully making me wait with each. Making me wait for each stroke going in, and coming out. It was pure torture. The anticipation of the next. But I loved every moment.

He withdrew and was waiting again, and this time longer than before. Then he whispered, "Tell me. Tell me again what you want before I will give it back to you".

I could say it now, without hesitation. It was easy to say it and mean it, because it was true, and I didn't need to whisper. I clearly spoke.

"Fuck my ass. . .Please? Give it to me. Fuck my ass like never before. Make me remember this fucking".

With those words, he immediately shoved the full length into me as hard as fast as he could - and this time he was bigger and much firmer. I exhaled and cried out from the unexpected shock of his full size. He climaxed inside me and I could feel his member pulsating, and his wetting me with cum - making it sloppy and lose.

I regretted it was over. I was actually sad. But I didn't want to appear needy. I'm sure he understood I could have taken more. You see, I've never had a climax with a man, and I had hoped, as I always hope, that this day, this time, would be different. But, we did not have more time that day, and unfortunately, we have not been together again since that wonderful day. I still continue to hope that someday I will again experience a lover who is this gifted.

Well, that's my fantasy story. I hope you benefited from it. The only part of the story that might be considered true (of this author) is the title: Waiting and Wanting.