Losing my anal virginity to an older woman.

Well, a little back ground. I grow up living in the same
house all my life. Our next-door neighbor was a lady that was a nurse. I think
she lost her husband in a car crash and was widower. I think she dated but we
never really saw anyone stay around. I can so see why. We all called her battle-axe.
You could tell she was always in charge and liked it that way. My mom was never
great at medical stuff so whenever there was a problem. She always nocked on
her door for help.
I would say that was the only time we would ever see a smile
on her face. She loved when people would need her help for something. That was
her weak spot.   
We I’m 30 now and my mom and dad were going on a trip and
wanted me to stay at there house to keep an eye on things as they will be gone
a month.
I was at my mom and dads and a couple of weeks in I was not
feeling good and it hit me. I had not used the bathroom is like a week. I look
around my moms house to find something to help with it and we had nothing. I
didn’t really want to go to the store but I had no chose.
I dressed and walked out and Mrs. M was just getting out of
her car as I was getting ready to get in my car. She knew I was there to look
after the house and so she tells me. I’m just next door if you need anything.  
Thank you, Mrs. M.
I get in my car and my stomach is not feeling good. I know
Mrs. M would know what to do as she was a nurse all of those years.  I see her and I say, Mrs. M you may be able to
help me. I walk up to her and get close as I’m a little embarrassed. Do you
have any stool softeners?  
She smiles and tells me, Oh yes Hun. Come in I will fix you
right up.
I have always felt safe with her as she has taken care of me
a lot in the past.
She comes out with the pills. She then asked me, how long has
it been?
Oh, I think maybe a week.
Oh Hun, that is a long time. This may not work. And if it,
does it will be for ever to run its course.
What should I do?
She walks away and comes back with a enema bag with a tube
on it and holds it up to me. She can see my look of “what the hell am I going
to do with that” look.
I knew what it was but never in my life used one.
She then said, I bet you have never used one of these.
No Ma’am.
She then tells me to fallow her. She takes me to her room.
She goes in her closet and comes back out with a silk robe.
She hands it to me and tells me. She will get the bag ready
that I need to undress and put this on.
She walks out of the room and I do as told. When she comes
back. I’m standing there in just the robe. She goes and gets a pad to lay on
the bed and tells me to lay on my side with my legs as she puts them. She walks
back in the bathroom and is looking for something. A few minutes later she
comes out.
I can’t find the Vaseline, She opens a drawer next to the
bed and pulls out some lube. This kind of shocked me. 1 I have known her most
of my life and never thought of her in a sexual way at all. So, seeing she does
was a little bit of a shock. 2  she was
always the battel-axe, who would want her? 3 at 72 does she have toys or a
lover?
So, she lifts the hose and shows me and end. I’m going to
lube this up really good and slowly slide this in. I knew that was what was
going to happen at some point. But I tried not thinking about it.
I see her put lube all over it and strokes it with her
fingers making sure it was lubed all around. She then rolls the robe up and
makes my ass hang out. She tells me to spread my cheeks and I think for the
first time. I’m embarrassed. I can’t look at her as I do this. Then I feel the wetness
on my star and I jump a little.
It’s ok Hun, I will make sure you are nice and lubed and go really
slow.
I can tell it is wet but at the same time it is nice and
warm. I look back and it is her finger on my star and she is lubing me up. Then
I feel the end on me and she does just like she said. She went very slow. After
it was in me, she rubs my butt a little and tells me she is going to start now.
That is when I felt her open it up and I started to feel
full. I told her and she helped me get use to it and she loaded me up. As she
is filling me up I see the lube bottle and it is warming lube and now I know
why it is so warm down there.
I moan as it is not the most comfortable thing to feel. I’m
trying not to think of anything as I need to hold it. At some point her hand
slides in my robe and she is rubbing my chest and tummy helping me relax.
Then I moan and my eyes jet open. At some point I got hard
and her arm just brushed over the head of my cock.  She rubs my chest and works down to my tummy
again. Sure enough. Her arm rubbed over my head again and my body shivered and
jerked.
She slides her hand out of my robe and tells me it is time
to get rid of this.
I go in the bathroom and do what I needed to do.
After I clean up really good and come back out and I’m
standing there in just the robe still. The odd part is I’m still kind of hard.
Not standing on end but not laying down. So, it is kind of sticking out. I see
her looking right at it. And I look down and see why she is looking and I turn
red.
She then tells me; we should make sure you are empty.
She tells me to get on the bed on your knees. I do as told.
She walks up behind me again and rolls the robe up and lays
it on my back. Then I feel lube running down my check and over my balls. I feel
her finger rubbing the lube all around and the feeling is…. Ok I will say it.
It felt so good. She is letting her fingers run all over. My ass, taint, my
little star. Then I felt a little pressure on my star and then in me. My body
is on its own now. I should be stopping her but my god please don’t stop I
think to myself.
It was not long and I can now feel her slowly sliding in and
out of me and I’m full-on rock hard now.
As she slides in and out of me more. I feel my hips rocking
with her. My moans are telling her everything she needs to know.
I can feel her going deeper and pushing something. What ever
it is I swear it feels like she it inside my cock.
I feel her speed up and working me a little harder. Fuck I
need to cum I think to myself.
I feel me pushing back to her finger as she fucks me with
it.
I moan out, “oh fuck “ “oh fuck I think I’m going to cum”. I
feel her push all the way in me and grind. I’m so close and I grab my cock. She
takes my hand off me and she tells me. Let me do that. She starts stroking my
balls as she works her magic in my ass.
My body is twitching and I’m just a moaning mess.
Then it hits me. I start to cum. She works her finger in me
harder and then she wraps her hand around my cock and starts to milk me dry.
I can’t take any more and I fall and roll to my back. I open
my eyes and she has a big smile on her face and she is licking her fingers from
milking me.
I dress and leave. Thinking, there is no way in hell I’m not
going back to see her.  

Source: reddit.com/r/Erotica/comments/rfluha/losing_my_anal_virginity_to_an_older_woman