My Ex Sister-in-Law Surprises Me Again
by Bill M.
05/22/08

My Ex Sister-in-Law Surprises Me Again

It was the Friday before New Year's and after a half workday, I rushed to my ex-sister-in-law's house.  We had been sleeping together for exactly a week, with my wife's blessings.  D__ was a 56 year old hottie who was great in bed and teaching me new things all the time.  I had led a satisfying but somewhat sheltered sex life until we hooked up.

I knocked at the door and let myself in.  She totally surprised me, wearing nothing but a very sexy frilly fire-red panties, bra, garter belt and fish net stockings.  Meoowww. Normally, she wore a flannel shirt and shorts around the house.  "Mmmm" I said, "you must have plans".

"I sure do.   Hop in the shower and make sure you go to the bathroom real good first.",

"Why?"

"Because I am going to stick my finger up your ass and rock your world" she said in a coy Texas twang..

I knew this was supposed to be pleasurable, but I had never had it done before.  The annual prostate exam certainly wasn't pleasant, but I put my trust in D__.

I took care of business, dried off and joined her in the bedroom, where we kissed and made out.  When I went for her panties, she said "Uh-Uh, not available"

"What do you mean??"

"I am having my period."

"WHAT???"

"You heard me – I still get my period every once in a while."

At this news, I turned a little ashen, as I had already shot three loads in her without a condom.  I assumed, 56 years, no way. No condom required.

She explained that she still had periods but they were hit and miss, so she was just starting menopause.  She also said there was zero risk of pregnancy.  She also kidded me that she could be a tempermental mother-fucker because she was going through menopause and I had better do what she said or she would kick my ass.  I said she had been that way for the last 30 years and we both laughed.

I am a confirmed pussy eater, so I asked if she was still up for it.  She said to knock myself out.  She lifted her butt and I eased her out of her panties, and yes, there was a little white string nesting in her bush.

I got down between her legs and stayed way high of the string, just using a steady twirling tongue action on her clit.   By this fourth  rendevous, I knew her nuances and what worked best for her and did the right thing.  When she got really excited and started moaning, I rubbed the outside of her asshole gently with a moistened finger, since I knew she really liked that and it helped her get off faster.  A steady pattern increasing in pressure coupled with stamina and a firm tongue and within about 10 minutes of loving attention, she was at the brink.  I slowed down at the end and did touch-and-go to play it out a bit, and then, when she at the point of no return, I plowed in hard with my stiff tongue and she went over the edge in flying colors.  Another job well done.   I got up and spooned beside her as she basked in the aura of post-orgasmic bliss.  She spoke first:

"I still get horny during my periods.  Thanks.  Most guys wouldn't even think of doing that."

 "No problem.  I really like making you come. What do have in store for me??"

She smiled a little devilish smile and asked me to get two clean bath towels out of the bathroom.  After I brought them back, she spread one out on the bed so the edge overlapped the far right corner of the end of the bed and asked to lay flat on my back on the towel.  While I did that, she went and got several loads of things, concealing them from me and put them at the floor at the edge of the bed along with the other towel.  Plus some pillows and a low padded stool so she could kneel comfortably at just the right height.
 
I joked "Are you getting ready to pray?"  "No, but you better!"

When she was ready, she leaned over and started stroking my hard-on and kissing it.

"Now, DO NOT CUM yet, I will tell you when you can cum, OK? We got a long ways to go and you don't want to spoil it"

"Aye, Aye captain"

She gently ministered to my stiff rod in a nice soothing manner, alternating hand and mouth for several minutes, sternly reminding me not to even think about cumming or it would spoil the fun.  I promised, staring at the ceiling, enjoying the attention immensely.  She was a skilled cock sucker.

She took a hand cloth cloth out of a bowl of water and wringed it out.  I couldn't see it, but I heard it.  She placed it over my crotch ahead of my still cock in the hair, sort of like a warming pad for my pubic region.  "This will help relax you".  Then she took a break and I heard first the snap of her putting on a latex glove and then the click of the top of the KY tube opening.
 
"Put your feet flat on the bed so your legs are up".
 
A few quiet seconds while my heart throbbed  and then she was rubbing warm KY in my crack with her left hand and searching for my hole.  I knew the hour of destiny was fast approaching.

"Relax"

"I will.  Is this going to hurt?"

"Not if you relax right.  It will be the best thing you ever felt.  I sacrificed my fingernails just so I could do this to my lovers".  She waved the fire engine red fingernails of her right hand at me.  As promised, the nails were all were very short and trimmed.

She found the tip of my asshole and rubbed around the outside for about a minute and then asked "Are you ready?"

"Uh huh"

It was really a non-event.  Her finger slipped in nicely and comfortably maybe an inch. After a little bit, she moved a little bit, then pulled it out and added some more lube and stuck it back in.

"How you doing?"

"Ok, feels good"

"OK, stay loose and don't tense up"

"OK"

Then she pushed up gradually higher and it became a little scary.  Her finger was now all the way up my ass and it felt enormous.

"Breathe in and out, slowly".  I complied.  She pressed on my pubic region with her right hand to help relax me.

"OK, now I am going to start massaging your prostate.  If it hurts, you tell me and I am going to stop, OK?"

"OK," I said, kind of scared

Actually, It felt wonderful. I really can't describe how good it felt.  Sort of a deep inside of you edge of a start of -an-orgasm feeling.

After a minute of soft massage, she took her finger out again, added more lube and pushed it back inside of me and resumed massaging gently.

"Are you OK?"

"Oh yeah, this feels great.  I never had this feeling before".

"OK, because it is going to get a little more intense".  She then massaged with more pressure pushing up against my insides in a finger wagging motion. My hips lifted off the bed and I sucked in air.  Sort of painful, but even more pleasurable as well. I groaned several times.

"Are you OK?

"I can take it, I said through partially gritted teeth"

"OK, I am going to massage it all the way down".  The pressure transitioned to more pressure but pure pleasure of an indescribable almost-orgasm type.  The ceiling was going in and out of focus as I reeled in the pleasure.

"Now, DO NOT CUM.  DO YOU HEAR ME"

"Yes, why?

"Because it is going to get even better, but I have more in store for you.  You want to go to the end, OK?

"OK"

At that, D__ slacked a bit off on the massage pressure and transitioned to an in-out movement.  At the same time, she leaned over the bed to take me in her mouth.  Pure Heaven, pure heaven, pure heaven…oh STOP, I am getting too close".

"OK, baby, you're doing real good.  Don't blow on me yet".  She immediately stopped touching my cock and toned down the massage pressure.   After a few seconds, she took her hand out, and the pleasure ratcheted down, but did not totally subside.  Sort of a warm glow remained/  She was taking off the glove as I looked at her, basking in my lazy pleasure.

"OK, baby..now I want you to get up on your knees, facing the head of the bed".  I lazily roused myself off my back and did as she asked.  She was taking me places I had never been before and so far, so good.  I was trusting her all the way.

She put her right hand on the small of my back, lubed my hole with her left hand and after a brief pasue, pushed something lubed up to the crack of my cheeks with her left arm, and then into my hole, something about the same size as the finger.

 "Does that feel good?"
 
 "MMM..yes".

With that, she did some hand maneuvering and it started to vibrate in my ass and waves of pleasure went out from inside me.  My cock throbbed and I could feel this weird feeling of something oozing inside my plumbing in my nether regions.  When I got more comfortable, she moved it in and out and it felt totally wonderful.  My ass relaxed.  It was a totally blissful state, not painful, not sore, but my cock really was feeling really swollen.  D__ reached down between my legs and stroked my cock a few times.  "Ahhhh"  She pulled her hand back and waved it in front of my face.

"Look at your precum, baby.  You must be enjoying it."  Her hand glistend with  more precum than I had ever seen before in my life, including teenage wet dreams.

"Its sooo good".  She continued this for several minutes and I meditated on the pleasure.

"I knew you would like it.  Are you ready for the next step?"

"I can hardly wait"

She took the unseen tool out of me and the pleasure departed.  I yearned for the next step, whatever the hell that was going to be.

"OK, now comes the tough part.  This is to teach you how it feels to be fucked in the ass, so when you are fucking me in the ass, you will know exactly how it feels and respect me".

"Is it going to hurt?"

"Err…well, I am going to show you how to do it right and the only way is for you to go through it yourself.  I am going to start off slow and easy and show you how its done right.  So it shouldnt hurt.  And if you ever hurt me, I am going to put a gun to your head and do it back to you the same way you did it to me, you understand?

"Yes maam".

At this, she reached back for more KY and fiddled out of view.   Then I felt something rubbing at my cheeks.

"Pull your ass cheeks apart, so I can see and don't hurt you."  I rested my kneeling body on my head and placed both of my hands on my cheeks and pulled as ordered.  I felt something moist and firm push against my asshole gently but firmly.  It was way bigger than anything before.  Actually it felt enormous, way bigger than my asshole.  As it was going inside me, it really began to hurt bad, intensely painful and I sucked in my breath uncontrollably with surprised pain."  I dropped my hands to my sides and pushed my body up in extreme discomfort and arched my back.  D___ halted the inward push.

"Don't tense, baby.  It needs to get in a little deeper and then it will start to feel good. Just relax, baby"  It still felt very painful, but after about a half minute, the pain subsided.  She pushed in a little more and – pop- the thing entered a space that didn't hurt at all.  But it still felt huge, enormous.  The pleasure was returning, but at a different level.  I had a huge thing in my ass and it felt..well…real good, but really large.

"How BIG is that THING???"
 
 "It's the same size you are, baby, so keep that in mind when you're fucking me."

"Are you ready to be fucked?"

"No!!"

"It will get better, I promise"

With that she moved it in and out a little, but I was sore and it ceased being fun. I asked again for her to stop.
 
"Just a little bit - you need to know what it is like".  With that, she made slow, deliberate thrusts in and out of my ass with the enormous unseen cock.  It transitioned to pleasurefule and sublime, but then started to hurt again."
 
"OK, I have had enough".

"OK", she giggled "Enough for one night. If you do it often, you learn to relax and  it gets to feel good and doesn't hurt at all if you are gentle and lube me right"  She let it sit inside me for a few seconds, then slowly eased the thing out backwards.  It stung going back out, but not as much, except at the very end.  I gasped.  Once it was out, I felt tremendously relaxed.  I looked around as she was wiping the thing off with a wash cloth.  True to her claim, the flesh-colored dildo was only as big in diameter as my cock, although the head was bigger with a mushroom and it was much longer.

"How far did you put that thing?"

"About this far" she giggled motioning about 4 inches.  "Keep that in mind"

With that, she took the wash cloth and cleaned me up, collected the towels and then disappeared into the bathroom briefly to clean herself up.

When she returned, she nestled herself between my legs and gave me a wonderful, slow blowjob. The throbbing from deep inside my ass added a new dimension of pleasure as she gamely sucked me to a terrific orgasm.  She choked on the massive amount of cum I let loose and pointedly let it drool out of her mouth to show me how much there was while she smiled.  "You had quite a load there!" she quipped.  But I couldn't answer her.  My thighs and abdomen had gotten so tense that when I came, they painfully cramped and I was able only to make silly baby sounds for a few minutes. Those muscles were sore the day after.
 
Afterwards, we lay there together and cuddled.  Then we fucked some more, but neither of us could come again.  We both were so excited that we masturbated in front of each other to a second orgasm, she using a very small vibrator thingy and me shooting my seed on her breasts and up to her neck. No facials, please.  Then we showered together, had a snack to eat and parted company.  I enjoyed rubbing her wonderful body in the shower and running my hands through her grey-streaked black short hair.

The next time we got together - New Years morning - she let me try out my newly-acquired anal skills on her to great mutual satisfaction.  I was surprised that she honestly enjoyed it and verbally encouraged me on in the throes of her passion.  After starting her with oral, we moved directly to anal.  She came with me inside her moving very carefully, as I had been taught, while she reached around and worked her clit to orgasm.  Her cries and moans were the real thing.  Her cum lust  stirred me on and I blew my wad in a particularly drawn-out and satisfying orgasm shortly after her.  We did it with a condom which probably helped me last longer than I would have otherwise. Her ass  was definitely tighter than her vagina and I enjoyed the naughtiness of it and the fact that she had surrendered her ass to me and liked it to  boot.  I was no longer an anal virgin.  She really enjoyed it in the ass (as long as she offered it to me first), which was a real turn-on for both of us.  She mentioned her last ex killed the goose that layed the golden eggs by being too rough and just taking it without asking.

We got together numerous times in the next month before she moved on to greener pastures.  All in all, she shared her ass with me 5 times, and that was the last time I had that or a total prostate massage/BJ from anyone .

Gosh, I miss her.

Bill M.