Episode 61: A Moment With Ann-Lee

My next sexual escapade came 4 days after my encounter with Chise. I was still super-psyched about my burgeoning relationship with Chise and the side-job of knocking up lonely Japanese women. When I logged on, I was half expecting more than one message from Karruche, but when I checked, my inbox was thankfully free from messages from that Vietnamese bitch. It was then that I had an interesting idea; when she next messaged me, and of that there was no doubt, I’d tell her that if she did not stop pestering me then I would report her to the police for what we did at school. But that idea was soon shot down when I realised that if I did report her, then she could and most assuredly would tell the police what I got up to with Ariadne.

She would also squeal to the police what I did with the other girls I was fucking. In short, if I reported her then she would cause more trouble than I could cope with. I was sat on my bed surfing the net when I got a message from Eliza:

Hey there my favourite patient, could you check out the woman on the website link please; she’s lonely and could do with cheering up.

I clicked on the link and checked out the woman. Her name was Ann-Lee, she was Chinese, 56 years old and had shoulder-length black hair. She was stood in her living room with her hands behind her head and was totally naked. She was older than all of the women that I’ve been with, but I had to admit that looking at her naked body my cock had started to get hard. I looked at the naked picture for a few moments and had to admit that she was half-decent looking. I sent a reply to Eliza:

Hi there, sure I’ll meet your friend

I sent the message and her reply came swiftly:

She’ll be at the office in 10 minutes; have fun

I got off the bed, put my iPad away. I grabbed my lanyard and slipped into my crocs and headed out of my room. And as they always did, I could feel the eyes of the nurses at the nurses station watching me as I left. I quickly made my way down to the office where I found that I’d got there before Ann-Lee had; so I sat in the armchair and waited for her to arrive. As I waited, I checked out the office and was pleased that it had been cleaned; hopefully not by Jennifer. She had been a good fuck, but like Christi and Nao, she had become to clingy. When she started saying she wanted a relationship with me, I knew I had to ask Eliza to get rid of her, which she did.

And much to my surprise, I began to rethink my relationship with Chise. I did not know why I was rethinking it but the thought did find its way to the forefront of my mind. Chise was an incredibly hot Japanese girl who had said she wanted to be my girlfriend; and to who I said I wanted to be their boyfriend. So why was I now beginning to rethink it all? I would be lying if I said that I was not having doubts about the relationship. I assuredly wanted to keep fucking Chise that much was certain, but the doubts about being in a relationship with her just would not go away. As much as I did not want to, I made a mental note to speak to Eliza about Chise, and maybe ask her why being in a relationship with Chise made me feel so odd.

My thoughts about Chise were interrupted when someone knocked on the office door. “It’s open” I replied, figuring it would be Ann-Lee and I was right. She stepped into the office and smiled at me. “Hello Jay” she says with a smile “It is nice to meet you”. I smile and get up from the chair and reply “I’m glad I can help you”. She closes the office door, looks me up and down and asks “Can we get naked and just lay down?”. I nodded and replied “Of course we can; whatever you want to do is what we’ll do”. As we began to get undressed, I noticed that she never took her gaze off me. “So, bed or couch?” I asked when we were both fully naked before each other. And I had to admit that she looked good naked for a woman of her age.

“Couch” Ann-Lee replied “I’ve always wanted to lay on the couch naked with a younger guy”. I smile and gesture to the couch and tell her “Then let’s lay down and get comfy”. We move over to the couch and I lay down then Ann-Lee lays down on top of me. “This feels nice” she says as she hugs me gently, to which I reply “Naked cuddling is always good”. For the next few minutes, we just laid naked on the couch in silence. I had to admit to myself that for a woman of her age, she actually felt good laid on top of me. As we laid on the couch, my erect cock kept poking Ann-Lee in the belly. “Sorry that keeps happening” I say, to which she replies “There’s no need to apologise; it feels nice”.

As we laid on the couch, I could not help but think just how fucking good getting my cock up inside this much older woman would feel. “I’m going to kiss you now” Ann-Lee said to me, and before I could say anything in response, she passionately kissed me. I placed my hands on her waist and held her as our tongues danced together. I once again had to admit that for a woman her age, Ann-Lee was a fucking good kisser. “OK, that was just what I needed” Ann-Lee says, breaking the kiss and sitting up “Now we can get down to the real fun stuff”. She takes hold of my cock and says “Stand up”. I got off the couch and stood before Ann-Lee, who kept a firm hold on my rock-hard cock.

Looking up at me, Ann-Lee said “Before we fuck, there is something I want to do to you”. She licks her lips, puts her hands on my hips and says “You just stand there and enjoy yourself”. She then leans forward and takes my cock into her mouth. She stays like that for a few moments before she began sucking my cock. As with every time I’ve been blown off while standing up, I had to fight to keep my knees from buckling. I looked down at the 57 year old woman currently blowing me and knew that she was by far the oldest woman to have ever done anything sexual with me; and that did not bother me at all. I smiled as I put my hands on my hips and watched as Ann-Lee went to town on my cock with her mouth.

As I’ve mentioned previously, I have always enjoyed blowjobs and the one I was currently receiving from Ann-Lee was no exception. She continued sucking me off for a few more moments before she stopped and said “You’re nice and hard; now we can have sex”. She got up off the couch and led me to the bed and said “Lay down”. I did as she told me and laid down on the bed. She gets on the bed and straddles my waist; she reaches down and places the tip of my cock inside her cunt and says “This is going to be so good”. Without another word, she slid down my cock, taking it all the way inside her in one swift motion. When it was all the way inside her, she looked down at me as she took my hands and placed them on her waist.

As she began to slid up and down my teenage cock, Ann-Lee became the oldest woman to ever have sex with me, and that did not bother me as much as you’d think. As I held her waist, I looked up at her and saw that she had her eyes closed and looked like she was concentrating on riding the youngest cock to ever get up inside her. I wanted to say something to her, but she looked so happy I decided against it. I moved my hands from her hips and gently squeezed her tits, which did not feel that bad if I am being honest. After groping and squeezing her tits, I moved my hands and put them back on her waist. For the next few moments, we fucked in silence which was fine with me as I might have mentioned that I enjoy silent fucking.

After a few minutes, Ann-Lee opened her eyes, looked down at me and told me “Let me know when you’re going to cum”. I nodded and asked “You want me to pull out?”. She shook her head and replied quickly with “No ... I want to kiss you as you cum in me”. That was fine with me, kissing when you cum can be really good but with Ann-Lee, I was more curious as to what kissing and shooting my load in a 57 year old woman would feel like. I did not have long to wait as after a few more bounces, I could feel the familiar tingling in my cock that meant I was soon going to cum. I gritted my teeth and said to Ann-Lee “I’m almost there; I’m almost ready to cum”. She looked down at me and said “Hold on for as long as you can; I want this to last”.

I gritted my teeth and did my best to hold off on cumming for as long as I could. “Keep going my naked white boy, KEEP GOING” Ann-Lee cried out “I’m just about there”. That said, she started bouncing up and down on my cock even harder and faster than she had been doing; it did not take long for the 57 year old Ann-Lee to cum. “I’M CUMMING” she cried out “I’M CUMMING OH FUCK ME A NAKED TEENAGE WHITE BOY IS CAUSING ME TO CUM”. Hearing her scream that and feeling her cum brought me to the edge of cumming. “I’m going to cum” I grunted through gritted teeth “Oh god I’m going to cum...”. I wanted to hold off on cumming for as long as I could, but it was no good as a few moments later my cock exploded its load of cum up inside Ann-Lee.

“I’M CUMMING IN YOU” I groaned out in pleasure “OH GOD MY BABY BATTER IS FILLING YOU UP”. I let out a groan of pleasure as I came inside a 57 year old woman. Ann-Lee stayed on my cock until the last of my cum was safely deposited in her nearly 6 decade old willing cunt. For a few moments, neither of us moved or said anything as we both came down. “Wow ... that was spot on” she says as she lays down on top of me. “Oh yes it was” I say as I hold her bum gently “You certainly hit the spot”. As we lay there, I had to admit that Ann-Lee was a great fuck for a woman of 57. She got off me and laid next to me, and for the next few minutes we just laid there in silence as our bodies cooled.

“Can I ask you something?” Ann-Lee asked, breaking the silence. “Sure; what is it?” I replied. “You really did not mind being with me?” she asked “I know I’m nearly 60 and not as pretty as some girls, so did you really like what we did?”. I slipped my arm around her waist and replied “Age is just a number; you liked me and I like you then who can tell us we couldn’t enjoy each other”. Ann-Lee smiled and replied “This is one of the reasons why you’re so popular; you always know just the right thing to say”. She kissed me on the cheek then cuddled up next to me. What I had just told Ann-Lee was most assuredly the truth; if two people liked each other then age was indeed nothing more than a number.

For the next few minutes we just laid in each others arms, enjoying the silence. As we laid there, I could not help it when thoughts about Chise drifted to the forefront of my mind. I still could not figure out why I was having second thoughts about being in a relationship with her. She was a fucking amazingly hot Japanese girl who wanted to be with me, so why was I having the aforementioned second thoughts about being her boyfriend? I made sure to bring this up with Eliza when I saw her next. “We should get dressed” Ann-Lee says, breaking the silence “I have errands to run and you might have other woman wanting to use you”. I nodded and replied “Makes perfect sense”.

We get up off the bed, move over to where our clothes are and begin to get dressed; and as we do I steal a few glances at Ann-Lee. I still can’t believe how good of a kisser she is and how good she was at giving head and fucking. Sleeping with her definitely changed my opinion on laying with women her age. It did not take long for us to get dressed, and when we were Ann-Lee turned to me and said “You were just what I needed; I will definitely want to use you again”. I smile and reply “You were just as good to; and whenever you want me, you know where I am”. She stepped forward and kissed me gently, then made her way to the door. “I will see you later” Ann-Lee said as she opened the door “It will be soon, I promise”.

She winked at me then stepped out of the office, closing the door behind her. Once I was on my own, I did as I always did and made sure that the office was neat and tidy. This did not take long as all I had to do was make the bed and straighten the cushions on the couch. Once I’d finished, I looked around to make sure everything was neat and tidy. Looking at the bed, I made a mental note to speak to Eliza about rearranging the layout of the office and perhaps getting a new bed. It was then that an idea popped into my head ‘I could make a note of any changes to the office I wanted then pass them onto Eliza’. I looked around and made mental notes of every change I would mention to Eliza.

Once I’d noted down what I wanted to change, I grabbed my lanyard and left the office, turning off the lights and closing the door behind me. As I left the office and made my way back to the ward, I knew that whoever I saw next, their age would not bother me one bit. I made a detour to the shop and got a cherry coke. I sat at the observation area near the ward to drink my soda and watch as the people came and went. As I sipped my soda, I watched as various women and girls came and left the hospital. I silently wondered if any of them would be my next fuck. Given my newfound acceptance of fucking women as old as Ann-Lee was, I realised that there was a whole new ocean of women now available for my cock.

Aside from the older women, I still enjoyed fucking younger women and girls. I wondered if I should ask Eliza about adding a section to the website that listed younger girls and women. After a few more minutes of people watching, I finished my soda and when I got back to the ward and my room, I was greeted by Eliza. “Hello Dr. Hottie” I say with a smile “Please tell me you’ve come to give me some medicine?”. Even though I’d not long finished seeing Ann-Lee, I was always up for some sexy fun time with Eliza. “I’m afraid not as I have rounds” she tells me as I sit on the bed “I just came to tell you about Chise”. I frown and ask “Is she OK?”. I was concerned for her safety but nothing more than that.

Eliza nods and replies “She’s fine, but she has had visas issues and won’t be able to come back for a while”. While I was pleased that Chise was now off my back, I couldn’t help but have a little joke at Eliza’s expense. “Visa problems?” I asked “Was the visa turned down by border official Eliza Hellruy?”. She looked at me with a faux look of annoyance and replied “Now would I really do that?”. Before I could answer, she added “Before you answer, I assure you it was nothing to do with me; she did not have the correct visa to return to this country which she tried to do once she was back home in Japan”. That actually made sense, and it was also a big relief as it meant I did not have to ask Eliza what I should do about Chise.