First Time Anal - The Second Time?

This experience happened 14 years after the one I detailed in "First time anal".

Yes nothing that occurred in that experience occurred again up to this point.

I had moved out of Sydney to Adelaide with a newly acquired job. Settling down to that and a new relationship with a lady I had now been with 6 years. Well the stars must have aligned or fait if you believe in that, because my lady had gone interstate for a meeting and while she as gone, I was at work and the phone rang.

I answered in the usual business manner:

"Hi, is this Michael?"

Yes it is", I replied, and who am I speaking to?

"It's Ray". Came the reply.

Well a shiver went down my spine and believe it or not my cock twitched. What followed was a long conversation of how have you been, it's been a long time, what are you doing now and where are you kind of stuff. Well it so happened that he was in Adelaide attending a convention.

"Have you got time for a catch up?" He said.

I asked how long he was in town and he replied.

"Only tonight and tomorrow night, the conference was introductory today and full on tomorrow. Are you available tonight after you have finished work?"

I replied that I was and we could meet in town for a drink if that would suit. I worked nights until 9:30 and had to go through town to get home so could meet him at about 9:45 at his hotel. He agreed, gave me his hotel and said he would be waiting out front.

All the memories can flooding back from that night he took my anal virginity, something I had recounted many times as food for my masturbations. We hadn't talked or seen each other in 14 years. Many questions filled my mind. Had he changed and gone totally straight, did he still lust after my body. I guess I would soon find out. I must admit a thrill went through my body and my cock did start to twitch again, but I must not get ahead of myself or my hopes up as a lot can change in all those years.

Well I finished work and headed for the city. My mind was a whirl and my palms a little sweaty. Then I remembered I was wearing sexy panties. Black silky, satin with lace trim around the waist and leg bands. I have been wearing women's underwear for many years now. What if he discovered them, what would he think of me, how would I explain it? Then sensibility took over. He is not going to see them, we are only going for a drink and if he did we would have gone too far for it to be a problem. The mind is an unbelievable piece of machinery the way it works and the thoughts it conjures up.

I arrived at the hotel and there he was waiting out front. I did a U turn pulled up and he hopped in. We shook hands, he hadn't changed much at all, maybe a little excess around the middle, but who hasn't.

"So, do you know any good bars around here?" he said.

To be honest, I didn't frequent the city much for social outings, so nothing came to mind. Then I thought about the hassle of getting a park and the thought of driving after a few quick drinks and couldn't afford to lose my license for drink driving. The police have become very hot on that recently and the limit is 0.05 which is about two drinks. So I quite honestly and innocently said why don't we go to my place as it would be much easier and I have a bottle of Chivas. When I said this I was honestly thinking of the parking and drink driving hassle, I did not have an ulterior motive.

"How far away do you live?" he asked.

I told him about 10 to 15 minutes. So he agreed with that as a good idea. When he asked that my mind was telling me he was not interested or into anything other than a drink and good chat. So I was relieved and disappointed at the same time, if you get my drift.

We chatted on the way about this and that until we got home. It was a pretty chilly evening so when we got inside I turned on the gas fire and got us both a Chivas on the rocks. One drink led to quite a few and as I said it was a cold night, so as I often do I got up and stood in front with back to the fire. He then also got up and joined me.

He then did something that I should have expected but it still took me by surprise. With a drink in his right hand he moved his left to my jeans covered cock, rubbed and slightly squeezed it, and said:

"How has HE been all this time, did HE miss me?"

An electric shock shot through my whole body and my cock has never got so hard so quickly. It felt so good to have someone else stroke and play with my cock. Just as I remembered it never reacted the same with anyone else as it did to his touch. I reciprocated by placing my hand on his trousered cock. Just as I remembered the touch, hard, fat long and thick. I asked how HE had been and he replied:

"HE has missed you too."

He then asked me if I had any porn. (Of cause I do) I said yes, want me to get it? He nodded. So I went off and grabbed one of my dirtier ones, men and women fisting and of course my favourite, pissing on each other. Put it on and pressed play. After watching and rubbing each other for a while, he came and stood in front of me.

He reached for my belt and undid it, then the button and unzipped my jeans. Kneeling and pulling them down to expose my panty clad hard cock.

"Nice, did you put them on just for me?" He laughed, as he knew that couldn't be true as I had them on before he phoned me.

Then he disposed of my boots, socks and slid my jeans off. Always a clumsy task the shoes and socks. He then, while holding my butt cheeks, buried his face in my panties, rubbing his nose and lips over my cock and balls and breathing his hot breath onto me which penetrated my panties and sent shivers up and down my spine. Every now and then we glanced at the screen to see fists, cocks, cunts and piss in all manner of ways.

Standing up again he unbuttoned my shirt and slipped it off. It wasn't cold next to the fire but I was shivering, standing there in only a pair of laced panties, my cock barely contained in them because of its hardness. It was at that point that Ray divested himself of all his clothes and closed into me to wrap his body against his. Two naked bodies (except for the panties) rubbing, holding, stroking skin on skin, warm smooth skin against his warm hot body. His cock rubbing against my cock and belly. The feeling is indescribable but I hope you can imagine it or it brings back memories.

He caressed my back up and down lightly and across my ass cheeks, then began to lick my neck, down over my collar bone, across my chest until his tongue reached my nipple. Swirling around it and nibbling. I have very sensitive nipples and they were now rock hard, jutting out into his mouth. He moved to my other one repeating the process before moving down over my stomach to the lace trim of my panties. Now kneeling, he rubbed his face and his tongue over the bulge.

Hooking his fingers into the elastic, he began to slide my panties down and I stepped out of them. His face was now level with my totally smooth cock, balls and pubic area.

"How long have you been shaving? He asked.

Oh a long time, I said, can't remember when I started but it feels so good when I am wearing women's underwear, soft and silky against soft and silky, you feel it and are aware of it all day.

He reached out with his tongue and licked my cock's tip, then swirled around the head. Even though I was standing back to the fire, a cold chill rocketed up my back and my whole body shivered. Lips then enveloped the head, it was swollen, shiny and purple, I had not been so hard for 14 years. His mouth started to move up and down, with each movement taking more of me into his mouth. My cock reached the back of his throat, which caused a slight gag, but he continued until my pubic bone met his nose. Interspersed with the bobbing he would take his mouth off and lick the length of my shaft, caressing the bulbous veins that were now a dark purple, protruding out like they wanted to explode. I cannot describe the feeling in words as they would not do it justice, so you can imagine the feeling yourself either from past experiences or experiences you hope or long to have.

This continued for some time. How long, I don't know as time had stood still. His hands were on my hips, then move to my ass cheeks, caressing them, squeezing them all over. Then he spun me around, running his fingers down my legs, my thighs my calves, up and down, causing goose bumps roughing my smooth skin. Placing his hands on both cheeks, he parted them, exposing me to what ever he had in mind or what ever he wished to do. I was putty in his hands. Leaning on the mantle piece, I bent over which moved my ass even closer to him. He licked each cheek all over then up and down the crease, which was now not so evident as I was spread wide. Settling on my hole, his tongue swirled around it, over it and probed it. If you have ever played with you ass, you will know what happens. That crinkled little orifice starts to relax as the crinkles involuntarily begin to swell filling with blood and it blossoms like a rose, giving total access to a tongue. My legs were trembling as I pushed back trying to get his tongue deeper, deeper I wanted it totally in me.

While all this was happening we were both intermittently glancing at the screen. All kind of things were happening, girl fisting girl, guy fisting girl, girl fisting guy, girl pissing on girl, guy pissing on girl, drinking, you get the idea. One of my filthier porn collection.

So while I was in raptures at the attention to my little hole, he stopped and said:

"I need to take a piss."

This was not surprising considering the amount of scotch we had consumed. Now while so turned on from what I was receiving and what I was seeing on the screen I asked him if he had ever pissed on anyone? He replied. No.

I asked if he would like to? He replied. No. I then went into pleading mode and was practically begging him to try it on me. I knew by now that he wanted to fuck me and I guess for him, if it was a means to an end, he would do it for me.

We went up to the bathroom, I climbed into the bath and lay down. He then stepped in and was standing above me between my legs. A beautiful sight, one of my favorites when watching porn is being under a guy looking up at his legs, cock, balls, stomach, arms, shoulders and face, feeling totally submissive. He held his cock and pointed it at me. The stream emanated from his cock and the hot liquid first hit my chest and then moved up over my neck and splashed my face. I opened my mouth and he directed it straight in. I swallowed and savoured the taste as he streamed it all down and over my body. The feeling is difficult to explain in words, but the warmth, the tingle on sensitive skin and especially on your cock and balls, making your balls retract and cock twitch. Also the wrongness, dirtiness of it accentuates the erotic pleasure which ravages your body. I took more of it in my mouth and swallowed before the tap was slowly turned off. I am pretty sure he didn't care for it, but then again why would he, he didn't get the physical pleasure that I did.

I then suggested we take a shower so I could clean up. After warming up the water I stepped in and he followed. Now my shower is not a large one in fact it wasn't designed for 2 people, so it was pretty cosy for both of us and hard not to be touching each other in the restricted confines. He took the soap and started lathering my body, making sure that none of my most sensitive areas were missed. The hot water, slippery sudd covered fingers began to cover most of my body. Taking a trip over my shoulders, arms, under arms, back, ass cheeks, thighs and of course cock and balls. Most of the time his rock hard cock was also trailing and slipping over my thighs, stomach, ass cheeks, cock and balls as he did so. Just take a few minutes to take that in (as I did) and enjoy the sensation.

He then turned me around to face the tiled wall and leaned in against me. I could feel his throbbing hard 7 inch cock rubbing up and down the crack of my ass cheeks. Still caressing my nipples, chest and stomach and occasionally moving down to rub my balls and stroke my now ridged cock. Now with each downward stroke, his cock would slip between my legs and on passing back would caress over my little hole. He did this again and again and as he did my ass started to relax and blossom, each time he put pressure on it with his cock head wanting to gain entrance. I so wanted it, so wanted that feeling again of him filling me, giving over to him, let him use me for his pleasure, hear the noises he makes as he takes his pleasures, making me so hot and satisfied at the reaction his body is having using mine.

But I had this nagging worry. I hadn't seen him in 14 years and I was in a lasting relationship. What if he had and infection of some kind and heaven forbid the big one. It is funny how in the throws of passion my mind could be so sensible. So each time he pushed, I moved and he missed.

This happened many times, he pushed, I moved, he missed, he pushed I moved, he missed, he pushed, I moved too late he hit. OH FUCK!!!! Too late and because of the state of arousal of my hole, he went straight in, fully, to the base of his cock and stayed there. Oh it felt so good, being so full, so open, so spread. The feeling of his fat hard cock deep inside me, filling me and my ass clamping down on him was so good, so right, so perfect, as it was meant to be. A sensation I had dreamt about, masturbated to for all that time was now upon me and electrically shooting through my whole body. Goose bumps, shivering, weak kneed, my body was a fireworks display going off. It was too late now, my body and his cock had betrayed me and all I could do is give in to the pleasure.

He drew his cock out to the head then slowly drove back in to the limit. Slowly, in and out, feeling my passage collapse as he drew out and expand as he re entered. Each time caressing my g spot, my prostate. I was in heaven, I had never felt like this before. Well I had, but this time it seem more intense. Then he picked up the pace. Faster and faster. My cock which had now shrunk as it usually does when something is working my anal passage, was flopping around from his thrusts. I found myself pushing back to try and get the maximum amount of cock as deep as I could. The sounds began to emanate, me: Ohhh mmmff, him: growl, groan ahhh, yessssss.

"I missed you baby, I missed this ass, it feels so good to have my cock home again. Ggrrrrg mmmmfffff aaarrrhh, yessss."

I said to him how much I had missed it and how good it felt. Because he was hitting my prostate constantly I told him he was about to make me cum.

"Your first, do it, let me know." He said.

Here it comes, I screamed, and he drove his cock deep and held it there. I erupted from my limp cock with a spurt that hit the shower screen, then another, then another. I have never cum so hard in my life. I could feel my ass gripping his cock with each pulse and contraction. The sounds emanating from him indicated it was having the desired effect.

"That felt so good." He said. "Now I am going to cum inside you, fill you, impregnate you, give you my seed so your body can absorb a part of me."

His words made me tremble, feeling so honoured that my body was his, his to be owned and used to leave his everlasting mark, stamp inside me. He started moving again, nearly fully out then fully in picking up pace like a stream train used to and in no time the wheels were blurringly spinning. Pumping in and out of me, the noises emanating from him made me hope the neighbours couldn't hear as they would have thought someone was being murdered. Squeezing my hips and pulling me onto him, he made one final lunge deep, oh so deep inside me, I felt as if he was in my stomach. Then I felt it, warm to hot, flowing liquid, shooting in spasms like a machine gun, spurting his cum deep in my bowels. So powerful, so strong, so hot, my legs trembling, if he wasn't grabbing my hips I would have collapsed on the shower floor. I could feel him trembling as he tried to expel the last of his seeds.

I was complete, I was whole, I was totally fucked. We stayed like that for minutes as I felt his cock shrinking and involuntarily extracting itself from my canal. I felt it shrinking and leaving, Please don't go, I thought. Finally, plop, it left and I fell to my knees. My ass was still spasming, the hot cum was exiting my now open hole. He reached under my arms and pulled me up and to him. Skin against skin, cock against cock, he squeezed me to him with his arms around me.

"That was even better than I remember the first time. You are so beautiful, my cock fits your ass so perfectly. It is as if our two bodies are one, each knowing how to satisfy the other. Thank you for letting me have you and your body.."

He then took the soap and started washing me, properly this time and shortly after I reciprocated with him. I only wish I had a plug so I could stop his sperm from dribbling out of me.

It was so sad that he had his meeting that day and couldn't stay. It was 5am when we finally dressed, well I didn't, I just put on my panties again. The taxi arrived and he was gone. Although I did call him on one Christmas, I have not seen or heard from him again.