Loving Mona...!

This is the Part-IV of a diary I jotted down to reflect on my relation with a lady friend of mine...obviously named Mona!

Since I am not sure of the allowable file size, I condensed the parts I, II, and III into this brief into, and then continued on with final part.

So let me start by telling you how Mona and I got started. I might also add if you are looking for an extreme hot sex between a totally-shaved, blue-eyed 18-year old blond goddess, and her young, virile, hot-to-trot, rock-hard lover, then you may stop reading this right now....it is nothing like that at all. So what is it about then...you ask! Well, I'll tell you:

This is about me and a lady friend of mine. We were introduced to each other by another friend of mine (Ronald), playing weekly mixed double social tennis for fun and exercises...which we still do to this very day. While Ronald, Mona and I were the fixed part of the quartet, a 4Th person that varied weekly used to make up the 4Th.

We were all mature (some going into our senior years), married adults (with unsatisfying marriages), and Mona was in her very late 40's. She was a wife, mother, and a grand mother! She was a little short and plump. Here bright smile and her demeanor, combined with a pleasant personality made up for her height, which also made her to look very attractive to me and highly desirable, as I am a sucker for well-groomed plump mature women. After months of playing tennis together...an opportunity once arose and we had some private talks about our lives. It was then I found out she has been neglected (emotionally, and especially sexually) by her husband, and there is a chance that we may hit it off and become closer and more personal! Her relationship with her husband looked very much like my miserable relationship with my wife, so there was a lot of mutual understanding of sort between us that showed maybe a sexual relationship might be something to be tried in this later part of our lives, where we were still able to enjoy the pleasures of sex.

Quite opposite to my wife and her shortcomings, Mona took her appearance very seriously. She would style her hair professionally every two or three weeks, do her nails nicely, and always have a subtle but light make-up on her face and eyelids. As a deprived older man, I was going really nuts about her. The idea of taking her to bed, making love to her, and hopefully introduce her to some anal intercourse was something I could not wait for much longer.

Don't get me wrong...she was not a push-over. It was said she is the one who wore the pants in her household…whatever that means! But her being a nice, pleasantly plump, even a church going decent woman from a small town in the Midwest was pulling something in me that could not deter a bit of my desire for wanting her.

So making it short; our dating started by me arranging a hotel room in a neutral nearby town, with me checking in on Saturday afternoon. She'd meet me there; we had a little lunch together, made passionate love, and went our own way later in the afternoon. We would meet once in every 3 weeks or sometimes once a month, after working around our scheduled tennis, spouses and other family matters.

This went on for a couple of months until in our last meeting I brought up the subject of anal intercourse (she had never tried it), explained it best as I could (Thank you Tristan!), and using a good amount of lube, I fingered her anus, made sure she gets used to feeling foreign object in her. She found the sensation tolerable. Guessing my enthusiasm, she mentioned maybe next time we try anal intercourse if it felt okay.

So below is the story of that meeting. Reason for writing it is the fact thinking about it...it still turns me on and I don't want to loose the memory of that day. And since this forum is called "Anal stories"...then posting about experiences of anal intercourse is not out of line! I hope.
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Next date with Mona was full of anticipation for me. I wasn't sure it would happen or not, but I sure did not mind to introduce her to anal penetration! Our intro into anal intercourse had gone well, I had fingered her anus on our last date to get her accustomed to the feel of having something in her ass, and she was sort of on the road to a tryout as we had discussed, but I still was not sure that would take place that day or not. As much as I wanted to try it, I certainly did not want to push her into doing anything she did not want, or she was not ready for. So I decided to take it easy and see how things go.

I had made reservation in another hotel this time. I recalled I had been in this hotel with another lady a couple of years ago. It was not as nice as our regular Holiday Inn Express off the Interstate, but what I remembered very well was the fact that the beds were lower to the ground. If we decided to try anal, this would put her ass just about the right height...so I thought. As it turned out later, my calculation turned out to be accurate!

I saw Mona drove into the parking and I went down to fetch her. She had again come from her hair dresser where she had her hair and nails done very nicely. She had cut her hair shorter, and the stylist had put a little mature Dorothy Hamil kind of flair into it, along with the customary blond highlights to lighten her hair and to cover the gray. She looked the best I had ever seen her. She commented about the room being smaller than and not as nice as the previous ones. I told her the other hotel was full and no rooms were available!

As soon as the room's door closed we hugged and started kissing. I could not let her go. She looked great, smelled great and was a delight to hold and kiss. I was really getting to like this woman.

We sat for the lunch I had brought and sipped some wine. We talked about a couple of unrelated things, like our tennis, Ronald's (our friend) health issues, car prices and so on. She got up and went to the bathroom to undress. I set up my little lube and lotion kit along with the baby-wipes on the night stand, closed the curtains, took my clothes off and crawled under the sheet, waiting for Mona to come out.

She got out of the bathroom with nothing on her top and a short loose pajama bottom. She looked really cute and her soft milky-white breasts had a very natural and real bounce to it. She looked very good and I felt lucky o have someone like her in the bed with me.

She lay beside me and we started kissing. I kissed her lips, face, neck and whatever I could reach to. Her lips were soft and moist and her soft shaved armpit tasted fresh and had her mild feminine odor I liked so much. Before I run my hand down to her crotch, she had removed the pajama bottom and was fully naked, but covered with the white bed-sheet. I run my hand down to her pussy which was a little damp from washing. I played with her inner lips a little and as she got more moist, I moved my finger over her clitoris and softly rubbed it. Her legs opened in excitement and she said in a muffled voice:

"Are you going to do my ass today?!!" That shocked me as I was not anticipating hearing this so candidly from her.

"Maybe honey...but not now. I would like to play with you a little, turn you on, and see you can have an orgasm first before I'll even try anything...okay?" I said assuredly, kept kissing her passionately and rubbing her clit.

A little longer of this foreplay, I felt she might be ready. I sure was. I climbed over her, looking into her bright green eyes; I slowly rubbed her clitoris with the head of my penis. I saw her eyes closed and she moaned lightly. It seemed a feeling of total arousal was coming over her. I was so glad I could please her with simple little things like this. As her moaning got a little heavier, she quietly whispered, "Don't torture me like that...go ahead and put it in!"

My penis went in smoothly into her wet, warm and soft pussy. As I started trusting I could feel her secretion was getting heavier and lubing us real well, if not a bit too much...but I did not mind at all. She was enjoying me fucking her and responding very passionately with her usual moans. Post menopausal woman's dry vagina theory was not valid with her. She was getting wet like she always did...more like a much younger aroused woman.

I kept fucking her and exchanging passionate kisses at the same time. I kissed her breast and sucked on her nipples so much they became twice as bigger as they were. Knowing how much I got turned on and liked her armpit, she raised one arm to expose her armpit for me to kiss and with the other hand propping up one breast so I could alternate kissing between the two. I was not the only one having a great time as I felt her legs were getting tighter around me and she started pressuring to get herself to come. I helped her by reaching her clitoris, rubbing it and fucking her with deeper thrust. Just a few more strokes, I felt her body stiffened and her orgasm started. She raised her legs further up making me go deeper in her pussy. The combination of my touch and the deep penetration was overwhelming her…and she started coming:

"Oh my God...I'm coming Jim...Ohh...Ohhh...Ahhh....Ahhh....Ahhhhhhhh.....O h my God....Ahhhhhh...!!!!" And she came with a few strong spasm that each seemed getting her pussy wetter and wetter. She was spent and mildly panting. Her legs unwrapped from my waist and laid flat on the bed, and her heavy breathing was slowly getting back to normal.

I stayed totally motionless for her to calm down and not be irritated by any friction from my penis, knowing in such a state of post-climax, everything in her pussy being so sensitive to touch. When I felt she was close to normal, I slowly pulled out of her and reached for a baby-wipe to wipe her crotch and butt clean without ever touching her sensitive clitoris.

I held her for a little while and we exchanged a few kisses. After she calmed a little more, she slid down and grabbed my semi- hard penis and put the head in her mouth...gently sucking on it and stroking the shaft. I responded quickly by becoming hard again. She kept on licking and sucking me for quite a while. I was really having the time of my life with my dick in her mouth until she suddenly stopped sucking. Perhaps it was a change of taste and feeling my pre-ejaculate that made her think I might be getting ready to come. She pulled my dick out of her mouth, turned over, kneeled with her butt up and told me, "Why don't you get behind me...I know you like it...?!" Wow...what a surprise! I obliged without saying a damn word.

I got behind her and spread the cheeks of her ass. Her big brown butt hole was nicely in view and very enticing. Her pussy, still a little red was open enough to be inserted without any effort, which I did and started fucking her from behind with slow but deep strokes. She felt great even if her inside was so loose and wet that I was getting in and out of her pussy with very little friction.

"Can I touch your butt hole hon..?" I asked, feeling she might be much willing at this point.

"Sure...go ahead... I know you want it!" She replied

I pulled out of her and before doing anything else, holding her ass cheeks open I kissed and licked her butt hole. She was clean to begin with and I had also wiped her after she had come. All I could smell and taste was the taste and smell of her cleaned anus and surrounding area mixed with a little scent of the wipe. It felt great and very sexy.

Her reaction to riming was a big surprise. After it sunk in what I was doing to her, she overcame her feeling of surprise and resistance. She relaxed her ass a little and got into enjoying what I was doing to her.

"No one has done this to me...ever...what are you doing?"

In between kisses and licks of her asshole, I said "I love anything that is part of you Mona...!!!", and then added:

"Next time you get mad at me at the court and tell me kiss your ass...remember...that is not a punishment for me...it is heaven..!" I commented.

"Well I tell you...you sure are strange...you are the first person done this to me...ever!" She admitted shyly.

"That's good to know...it’s called rimming...maybe I be the first do other things to you...!" I hinted.

"I am sure are going to...aren't you little shit...?!!" She said with snide remark but with a friendly tone.

I suggested she turn sideways and come down to edge of the bed. This way I could stand on the floor and she be kneeling in front of me for fingering her anus. She obliged, turned and scooted down to the edge, stayed on her knees with her feet just hanging out of the side of the mattress. Standing on the floor behind her over the bed, I put some KY lube on my finger and her ass, rubbed in over her asshole. As soon as as I felt her hole is relaxed, I pushed on it a little and my finger went in easily.

"Honey I am just doing this you get the feel of it and relax your hole" I said. I stroked her gently with my finger which was going in and out with no resistance. Then I add a little more lube to her anus tried something a little bigger...my thumb.

Using a little more KY, I gently laid my left thumb over her anus and with a slight push, her asshole opened up and my thumb went in. I kept it there for her to get used to it. I pulled it out and put it back a couple of times and seems she could take it with ease. With my left thumb still in her ass I asked her:

"Honey...is this hurting you?...Can you relax with it in you?...Please let me know if it hurts...okay!...Very important you tell me!"

"I will tell you if it hurts and if I couldn't take it..." She said.

I lubed a little more with liquid KY to cover a bigger area and my thumb maneuvering around in and out of her. It seemed her butt hole had adjusted easily to the foreign object in her ass and could take it. I put my dick in her pussy and started fucking her with my thumb still in her ass. I could feel my penis through her rectum/vagina separation wall and it was an amazing feeling. Thinking she maybe now could take my dick in her ass, I pulled out of her and asked her:

"Honey..would you let me try gently see my penis will go in you..?!!"

"Yeah...but very gently..." She said.

"Of course...and please promise to tell me stop if there is any serious discomfort...okay!"...She nodded "'Okay...!".

I opened her cheeks again and asked her if she can reach her ass and held her cheeks to free my hands. She reached back and grabbed the cheeks of her white ass and pulled it open. Her asshole popped in the view while stretched slightly by pulling her cheeks and the ridges nicely in clear view. Those beautiful red fingernails against the white cheeks of her ass opening her butt hole were creating an amazing contrast and it looked sensational to me. This time I put a little more KY oil on her anus and rubbed some on my dick. I grabbed the shaft of my cock, rubbed its head over her nice big brown asshole she was stretching in front of me. My cock's head pushed her near-open hole slightly further apart and I gently slide it in her. I let it smoothly go about half length in, and all heard from her as a gentle "Oooh..!".

After waiting a few seconds for her ass get used to having my dick in it, I gently grabbed her hands and helped her put them back beside her as before. Her cheeks closed back on my cock. I held her cheeks slightly open and started a very, very, slow motion in and out of her ass. It was heaven!

"Honey, am I hurting you...do you need more lubricant?" I asked her

"No...its okay...there is a little pressure but does not hurt bad...!" She replied

She was lubed well. I was hoping she is comfortable and it did not hurt her. I did not want to turn her off now that we have come so far and my dick is finally in her ass. "Doing your ass feels so great hon..." I confessed.

There I was on my feet, with my dick in Mona asshole, holding her hips and fucking her slowly. It could not have been any more pleasurable and it felt great. The bed turned out to be just the right height for our first anal experience. The scene was not at all what you would imagine in a hard-core anal porn movie, where a huge cock forced in and in and out of a stretched asshole ferociously with every detail showing in close up. Not that at all...her big ass cheeks were covering most of my penis and her anus was only partially visible with my dick in it. I could see no more than an inch of my penis and the rest was her ass that filled my lap. I like the feel of deep penetration than a posing-for-picture stance that looks good only for a photo shoot! Getting gradually deeper in her was creating an amazing sensation. Thinking to myself how come something so harmlessly pleasurable for two consulting adults be looked down in our puritan society with such a negative social stigma.

The scene; that is fucking Mona in the ass with her nice hairdo and those long nails laid out over the white bed sheets were overwhelming me. I could still see her white milky breasts sticking out from the sides of her chest. I kept the strokes short for her comfort. Her ass was tight and I could feel the head of my dick passing along those silky smooth walls of her rectum which felt wonderful. The lube was doing its job and seemed it had coated inside of her rectum for a nice gliding action. I did not want to fuck her ass too long here on our first anal experience...thus, once I felt I was coming I didn't drag it on. I pulled her hip toward me and inserted my dick gently all the way deep in her ass and held it there. My climax started from the base of my cock and reverberated all the way through into her ass. I couldn't keep quiet and hollered:

"Oh baby..I am coming hon...its coming in your ass babe...ohh...ohhh...ohhh...God...ohhh..baby...wow. ..!!!" I shot a big forceful load of semen into sweet Mona's rectum with multiple bursts. It was one of the most satisfying orgasms I had in an anal experience. It was just great.

After waiting in that position for half a minute, letting myself enjoy the pleasure of the moment, I slowly pulled out of her and held her cheeks open a little to see if she gaped. She did not. Her hole closed nicely back into shape with just maybe a 1/2 second worth of a small gape. Her anus looked puffier now and I was hoping I had not hurt her. With all the lube I had used and gentle movement, I didn't think I could have hurt her...and I do not have a big thick cock, which makes me well suited for anal intercourse.

I wiped her off a little and went to the bathroom to wash my hand and cock. I returned to bed and laid down. Then she went to the bathroom to sit on the potty and push out the cum and get cleaned up. I had a feeling of excitement and satisfaction that was hard to describe. I just had started Mona, a fifty-year old plump, sweet, friendly, church-going lady friend of mine to her first anal intercourse of her life, and had one of the best orgasms of my life. I asked her feeling about that and she briefly said:

"It is a little different..don't you think?"

"It certainly is hon...I can't tell you how much I enjoyed it. Hope it did not hurt too much and you enjoyed it..at least a little...!!" I said.

"It was a little pressure at first when you went in...but then there was a good feeling sort of..." She replied rather frankly.

"It was our first time and I did not want it to go for long. But when women get used to it they find pleasure in it because the penis rubs their G-spot from the other side."

"Well maybe...but takes a while to be comfortable with it...I guess"

"You are absolutely right...it takes some time to be comfortable with it...and it is not something you do all the time!" I confirmed

"Maybe once in a while...okay?!" She said.

"Okay...I am so grateful you allowed me to try it with you...I makes me feel very close to you...!" I said sincerely.

"Oh..that's okay...I knew you had some plans for me you little shit...was I clean inside or messy!" She asked shyly.

"You were squeaky clean hon...nothing to worry at all...nothing...I promise you...!" I replied.

I laid beside her, kissed her, and did my best to assure her occasional anal sex is as normal as vaginal sex...a lot of women do it, but its the wrong social stigma that makes it a taboo and a not much talked about subject. Out of nowhere, she blurted:

"And I want you promise me our friend Ronald will never know about us...especially about today's event! I know you men talk..." She sounded serious, and understandably so.

"Of course dear..you have my word on that...besides, he will kill me if he finds out...he feels very close to you and I am not going to say anything to jeopardize what we have...!" I replied with a firm and assuring tone of voice.

In keeping a dialog going and a silence not to linger on, I said "Do you think being around me you experienced things that you probably had not tried before...like doing anal!!"

She let out a big laugh and said "Damn right...being on top was not new...but this was something else...I feel like I lost my virginity...ever thought of that?!" We both laughed at her comment.

I did my best again to assure her this is not that abnormal as it sounds and is practiced widely. We hugged, kissed and made out a little more and then came the time to say good bye for the day. We both got dressed and she touched up her makeup and set her hair, looking very proper...not all like a woman who had my dick in her mouth, pussy and ass just a while ago! I took her to her car (a van by then), got her in and waved good bye. We decided to meet again maybe in three weeks when the logistics could be arranged and the coasts were clear.

It has been almost 3 years from those first dates. We still meet once a month or so, have a lunch, sex, and occasionally anal sex. She got used to having anal intercourse but she never got an orgasm just by anal penetration. A time or two she made herself come rubbing her clitoris with her small vibrator when I was in her ass. She has been open sexually and her initial inhibitions to anal sex have almost evaporated. She looks prettier to me now than ever before. She claims having occasional sex, orgasm, and takings my ejaculation both vaginally and anally has balanced her hormones...and attributes that for her softer feeling skin and less blemishes! I don't know about any of that and am not sure if it is true...but I do not disagree with what she feels about herself and will service her as long as she lets me. Of course being sexual with her has made us closer to each other but I think having anal sex with her has somehow made as even more close and we have become very intimate. Sometimes playing tennis we change looks that only two of us know the meaning.

As the time went on, her ass got much better used to penetration. It is easier every time to enter her... but I make sure I always use a lot of good lube (and lately, Astroglide Gel) on me and in her anus. We even discussed and she tried a quick lukewarm water enema to clean her insides. She feels better when she knows she is clean, but she has been always very clean...I love it! All I got to do is massage her anus, put a finger in and then a thumb for stretch, and enter using sufficient lube and a good dose of Astroglide Gel. She takes it in nicely and her rectum feels delightful to be in. I still fuck her very gently and avoid being rough when I am in her ass.

We still meet regularly for tennis but Ronald has dropped out due to health related problems. Getting to know Mona this closely, having sex with her and introducing her to the thrills of anal sex have been a very pleasurable trip in my sex life. We can't meet as often as we like, so when we meet, we are both hot for each other. I miss her when I do not see her intimately often, and always have a craving for her plump body, her moist vagina, and her brown puffy asshole. She has been like a sexual gourmet to me who still remains my very good lady-friend and a fair mixed-double tennis partner. I couldn't ask for more.