Meeting Maxi

Story Info
Helping a MILF overcome her sexual inhibitions.
2.9k words
4.42
36.4k
33

Part 1 of the 4 part series

Updated 06/08/2023
Created 02/05/2017
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
MaxiMilf
MaxiMilf
227 Followers

I had been divorced for about 5 years. My wife of over twenty years divorced me after she took up with our neighbor. She broke my heart and it took me a long time to get over that heartbreak. I started coming around last year when I met Maxi who taught me how to trust women again. Up until Maxi, I had not dated since the divorce. I just couldn't see myself in another relationship, making myself vulnerable again. Maxi brought a light into my life and reawakened my libido.

Maxi showed up one day as a temporary Receptionist at my job. I walked out into the Reception area one day to greet a visitor when I noticed Maxi behind the front desk. We caught each others' eyes for a moment and something sparked between us. Actually, I felt like I got hit by a lightning bolt. She had the most seductive brown eyes and cute little turned up nose. Later that day, Maxi and I met again while we were getting coffee in the break room. We quickly struck up a conversation. We're both around the same age - mid forties. She is about 5 feet 5 inches tall with a compact, tight body, just a tad on the full figure side. Though small in stature, one of the first things you notice about her is her tits and ass. In a word, both are outstanding. She's got a 40D rack and kind of a Latin bubble bootie, with shoulder length chestnut hair, just a bit on the curly side. And, of course, the brown eyes that got my attention the first time I saw her.

As we spoke, we realized we had lots in common. She lost her husband at about the same time my wife started cheating on me. Only, tragically, her husband was killed in an accident. She was still not over it after five years, and she shared with me that, though she got asked out quite often by many men, she always declined, feeling like it would be cheating on her dead husband. For some reason, because she felt so connected with me, she agreed to go out to lunch with me later that week. Our bond was really incredible. It was a long time since I was able to relax with a woman and share stories and details of my life. We just had this incredible connection. It wasn't long before we began to date regularly. The one problem in this new-found relationship is that Maxi just couldn't get beyond kissing and petting to full-on sex. She told me she had this kind of emotional and physical block when it came to sex, and confessed that she had not been with any men since her husband passed five years ago.

Because of the chemistry between us and, frankly, because I was having such a good time, enjoying once again female companionship, I didn't let the lack of sexual activity get in the way of a good thing. But I have to tell you that there were many nights I went home after seeing Maxi, with a severe case of blue balls, something I hadn't experienced since I was 15. I would have to relieve myself by fantasizing about Maxi and jerking off like a horny teenager. Maxi knew that my frustration with the lack of sex was beginning to put a strain on our relationship. We talked about it often, and she confided that she was seeing a therapist. She said she was making progress and that the therapist told her that she needed to take what he called "baby steps" to rediscover her sexuality. The fact that she was in a committed relationship with me, someone who is trustworthy and not looking to take advantage of her sexually, was a positive sign to her therapist. He felt that in time, she would be able to have a normal healthy sex life with me. This is a story about those steps Maxi took with me to get back her sexuality.

The first step came one Saturday afternoon. Earlier that week I had wrenched my back pretty badly, so Maxi said she would come over Saturday to make me dinner and help me around the house. I was relaxing in the back yard getting some sun when I heard Maxi pull into the driveway. She stopped in the house, and then came around back and as usual, I couldn't help but drink in her sensual beauty. I only had to think about Maxi and my cock would begin to strain against my pants. She had on thong sandals with cute manicured toes painted in red, cut off white shorts, and a tight black top. Her hair was done up in a bun. Her tits and her ass were accentuated by the outfit. The woman was built for sex. She greeted me with that sexy smile of hers and came over to sit with me, surprising me with two glasses and a bottle of sangria. While we drank and relaxed in the spring sun, she told me that she felt badly that I hurt my back, and that she had the perfect way to help me feel better. Before her husband took ill, they would regularly give each other massages,and she apparently became quite good at it. She's telling me all this and I'm sitting there getting hornier by the second, wondering where this was going. I nearly fell out of my chair when she suggested we go inside and she treat me to a massage. Of course, I wasn't about to resist, thinking that this could be the moment I had been waiting for. "I'm finally going to be able to make love to Maxi," I thought. But a small part of me wasn't holding out too much hope.

"C'mon," Maxi said. "Let's go get you that massage. You go in and take a hot shower and I'll be waiting in the bedroom."

When I finished my shower, I wrapped myself up in a robe and headed in. Maxi did a great job of setting the mood with several candles and soft music. I was a bit disappointed when I saw that Maxi hadn't removed any of her clothes. But hey, I figured, this is at least a step in the right direction.

"OK, face down on the bed, and I'll be right back. I'm just gonna get some oil that I heated up in the microwave."

"Should I take the robe off?" I wondered. I didn't want to presume too much so I kept the robe on. A few minutes later, I heard Maxi as she came back into the room.

"Now how am I supposed to massage you with that robe on?" she asked incredulously. OK, at that moment, I realized things were getting serious. "Here's a towel. Take that robe off and wrap the towel around that cute little butt of yours," she demanded. I did as I was told and also did my best to hide my hardening cock from her. I didn't want to scare her away.

In a few minutes, Maxi started her massage. She poured warm oil on my back and started rubbing from the base of my neck down my spine. The feel of her soft hands was absolutely amazing. And it was becoming difficult to keep my straining cock in check while I was lying on my tummy. Slowly she made her way under the towel and began to massage my ass cheeks.

I heard her say, "Let's get this towel off of you. It's only getting in the way."

She quickly flicked it off of me and then went back to work massaging my ass. Working her way down my thighs, to my calves and feet, she slowly parted my legs. Moving back up to the inside of my thighs with long strokes, she grazed that area between my balls and my ass, alternating between applying soft pressure and light, massaging and tickling. It was as if I had died and went to heaven. I could feel the precum leaking from the tip of my cock, and I knew that with my legs spread, she got a really good view of it.

"OK, time to turn over," Maxi whispered into my ear.

Suddenly I was filled with panic. "Listen Maxi," I said in an apologetic tone. "I don't want to make you uncomfortable or anything, but you know what you're going to see when I turn over, right? If you want to stop here, we can. I mean, I can't help my reflexes."

"No, silly," Maxi replied. "It's just a massage. You don't have anything I haven't seen before. Now flip over and let me do your front."

What else could I do? The towel was gone by now, and even if I had it on, it would have tented and wouldn't have done much good anyway. So, I did as instructed, and there in all its splendor was my 9 inch cock, as hard as a steel rod, pointing due north. When Maxi got a glimpse of it, her eyes lit up and her mouth opened.

"Holy shit. Talk about reflexes! That's the biggest cock I have ever seen. My husband's was only about half that size and no where near as thick. That's what I call a hard on!"

"Look," I told her. "As I said, if it makes you uncomfortable, we can stop right now."

She stammered a bit, and licked her lips and then she said "No," with a little hesitation, "That's...Well...that's OK...I guess. Let's finish your massage." Her mouth was actually watering as she continued to stare at my cock. And although it was as hard as a rock, as she stared, I felt it getting even harder, the mushroom head about to blast off like a rocket. She rubbed some oil into my chest, but it wasn't long before her perfectly manicured hands traveled a bit further down, rubbing the inside of my thighs. Meanwhile, my cock was twitching, and a liberal amount of precum had coated the head, which was completely swollen and purple at this point.

I nearly jumped off the table when I felt Maxi's soft, long fingers begin to lightly stroke my balls. Without saying a word, she slowly trailed her index finger up the backside of my cock, stopping at the base of the head, swirling it around a bit and then returning to the base. She did this several times before going back to the head and massaging the precum around the opening. She worked both her thumbs in a circular motion around the tip and then back to that spot behind where the head meets the shaft. That's the most sensitive part of my cock. She was keeping me on the edge, stimulating me enough to drive me crazy, but not enough for me to come. It felt like every nerve ending in the head of my cock was firing at the same time.

She said three or four times, perhaps not realizing how many times she said it, "You have an absolutely amazing cock."

This went on for quite some time, and I was just about ready to lose my mind when she dribbled some oil on the tip and let it flow down the shaft, mixing with the precum. Then she encircled and gripped the entire shaft of my cock with one hand, while rubbing the tip with the palm of the other. Her grip on my cock felt incredible. Then, ever so slowly, she brought one hand down over my shaft, rubbing my entire length, followed by the other hand coming down making the same motion. She repeated this move several times. When she stopped, she gripped my cock just before I was about to come. It was as if she knew exactly how close to the edge I was and when to stop just before I couldn't hold back any longer. After a slight cooling off period, during which time she tugged on my balls, rubbed the inside of my thighs, and played with my ass, she started up again on my hard on. By now, the oil on my cock had dried and left more of a pasty film. She gripped my cock again with one hand and alternately gripped and relaxed her hold on it. Grip and relax, grip and relax...several times quickly. This was a strange sensation since the pasty oil stuck to her hand slightly as she relaxed her grip. The skin on my cock would pull back slightly each time she relaxed her grip, offering a completely different type of stimulation than I had ever felt. While she was doing this, with two fingers from her other hand, she began to rub the spot between my asshole and my balls. And then, just as before, she stopped just in time. While this was driving me completely nuts, I really didn't want to come. This felt way too good, even though my cock was raging and practically begging for release. I could hear myself moaning and had not control over what was coming out of my mouth.

Maxi asked me to turn over and get on my hands and knees.

"What in the world is she going to do now?" I thought. I soon found out. Once she had me positioned, she let some oil drip down my ass crack and down to my balls. She began to massage my balls gently with both hands, tugging on them gingerly every now and again. When Maxi stopped massaging my balls, she softly ran her nails over my ball sac. The scratching just heightened my sensitivity. This next move came as a total surprise to me, as I had never even thought that anyone would do this and that it would feel so good. She placed the palms of her hands on opposite sides of my ball sack and slowly slapped my balls and rocked them from side to side. The slight discomfort that I felt in my balls was edgy enough to feel good, but not hard enough to cause me any pain. While still on my hands and knees, she gripped my cock with one hand and then massaged my asshole. Maxi stopped just short of inserting a finger. As you can imagine, I was completely losing my mind.

"How does that feel?" Maxi asked seductively.

"Max, I'm fucking losing my mind here. You have got to make me come. I can't take it any more."

"Not so fast, you horny boy. I'm having too much fun."

It was like she was a different woman, with no inhibitions whatsoever. Next thing I knew, I was on my back again, and Maxi was kneeling in front of me on the bed. God, I never knew there were so many ways to give a hand job. And I was completely shocked by Maxi's uninhibited behavior. I think at that moment, I would have offered to pay all of her therapist bills. The guy had to have been a miracle worker. Whatever it was, I was loving it.

Pouring my oil on my cock and rubbing her index finger around the swollen head, she asked in a more demanding way, "What is it you want me to do?"

"Make me come. Please make me come." I begged her. She placed the palm of each hand on the front and back of my cock and she began to gently rub up and down, finding a rhythm. My hips were rocking with every upward stroke. But she wasn't applying enough friction to bring me over the edge. I think she did that on purpose. "Faster, harder" I begged. She slowed down just long enough to reach up and kiss me passionately, entwining her tongue with mine. I begged her once more, and with that, she resumed the hand job with her palms, this time applying more friction and speeding up the pace. I felt myself nearing the edge again and I implored her, "Maxi, please don't stop."

"Don't worry lover, I'm going to make you explode this time. I want your hot come in my face."

Applying just the right pressure, she brought me to the edge and somehow held me there for what seemed like an eternity. I felt a pulsating sensation begin in my feet, up my legs, and through my cock. "Aaaaargh! Oh God that feels so fucking good. I'm coming. Oohhhh." Three long ropes of jism shot up and hit her in the face and in her hair. She continued to milk me, until the last remnants of come dribbled out of my cock. Maxi released her hold on me, covered me with a blanket, and cleaned me up. I fell into the most satisfying sleep, cuddled up to Maxi.

From that time on, our physical relationship intensified beyond anything I could have imagined. This was truly the best sex of our lives. Just think...If I wasn't patient, I could have lost Maxi. But she was well worth the wait. She is now completely uninhibited in bed and does things to me that you only see in porn movies. She was worth the wait. In my next installment, I'll tell you about some of the other things Maxi and I did when her "baby steps" progressed and her inhibitions slowly melted away.

MaxiMilf
MaxiMilf
227 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
5 Comments
dommasterjimdommasterjimabout 1 year ago

........ Incredible *5*

AnonymousAnonymousover 1 year ago

Wow - amazing Maxi! Great description of progression. How did MC last so long? Very erotic

Tw0Cr0wsTw0Cr0wsalmost 7 years ago
what is wrong is...

When will people learn bra sizes?

40D means a rib cage 40 inches around.

That is not compact or small.

The D means four inches larger than the rib cage.

That isn't much.

But a big part of the problem is that many large breasted women wear the wrong size bra, she might be wearing a 38C when she should wear a 34E.

So when a man picks it up off the floor to read the tag he can only get the wrong idea.

AnonymousAnonymousabout 7 years ago
Icecubes

That has me so riled up that a cold shower is not going to calm me down - I think I will need to lie in a bath of ice cubes to try and settle my body down.

AnonymousAnonymousabout 7 years ago
superb

Can't wait for part 2

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Seduced by Best Friend's Mom Pt. 01 Best friend's mom is an MILF and she seduced me.in Mature
My Best Friend's Hot Mom Young stud bangs MILF in all 3 holes during hot summer day. in Mature
MILF Addiction Ch. 01 An 18-year-old boy helps his girlfriend's mom in her garden.in Mature
Ms. Jackson Ch. 01 Boy is torn between his longtime girlfriend and her sexy mom.in Mature
Charity Begins Next Door Life isn't fair. So when you fight back, fight dirty.in Romance
More Stories