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Tillie, Mom’s Best Friend

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Aunt Tillie

This is a fantasy based on actual events in my earlier years. There was an “Aunt Tillie” whom I lusted after, but since she was mom’s best friend…

I disabled comments because of the grammar Nazis and naysayer. I am not a professional writer by any means.

This took place in an established old, very religious northern city which was extremely conservative. read: prudish.

Tillie, or Matilda was her birth name, was my mom’s best friend all through high school. Both of them married a year or so after HS but remained close friends, as my mom had no sisters, so Tillie became a de-facto “Aunt” to me. She came to our home at least twice a week. Tillie wanted children and her husband, Hank, did not. So, the ensuing fights led to divorce after 18 years of marriage. There was no alimony for her, as Hank split the scene short after the divorce; however, she had a better paying job than he. Financially she was doing OK. At the time of this story, my mom and she were in their later thirties.

Tillie at this time, was 5-4, about 115#, and very well-toned, as she was on the girls’ swim team in HS, and still swam at the “Y” three times a week. She said the physical activity kept her feeling young. She had a “B” cup, and her leg and hip muscles from swimming gave her some sleek sexy curves. However, she dressed “granny” style: long, baggy dresses and skirts, loose blouses, light brown hair usually up in a bun. Sort of like a 1920s stereotype of a secretary. IMHO, she was fending off men.

Myself. I was 5-7, a skinny 127#, and had really bad eyes from birth and wore “coke-bottle” glasses, read– nerd. I was good in school and landed a scholarship to a local college. I was on the swim team in school, doing the “butterfly” stroke, and held my own at the meets. For those who are not swimmers, that stroke is very hard to do without “breaking stride” and be disqualified. However, the swimming aspect helped in school, as it helped me get the scholarship.

My parents. Mon was 5’2, with extra pounds, but had C cup tits, with quite a droop. She was a real prude. On time she opened the door to my bedroom to wake me, and the sheet was off me exposing my morning wood. She asked me if I needed to go pee? Yeah, right! She was a control freak as in O C D. Had to be in charge or she went ballistic.

Dad was 5-6 and was fat, however, he drove a delivery truck and unloaded it himself. I saw him pick up a 55 gal drum full of kerosene and place it in the truck bed. That’s 300+#. He had a gross and sometimes vulgar, sense of humor which got worse after he had a few drinks.

They both had friends from their younger days, and that they played cards at someone’s home every Friday night. Dad and mom each had their own group; however, since all of them were raised in the same neighborhood, they knew each other. The night starting this story, it was Tillie’s birthday, so ALL their fiends were at our home, and I was asked to stay. Usually whenever they played cards at our house, I got the car keys and went somewhere with my friends, for my mental health

So mixed drinks were poured and all had a few. I stayed with beer for the time being, knowing that after a few, Dad usually got a bit gross, and everyone had a big laugh. Remember, this group was otherwise very conservative that way.

Dad went to an “adult store” (out of town) and bought some very sexy bikini underwear for Tillie. (I told you about his sense of humor). She opened the package and immediately turned bright red. Everyone else sat there with their mouth open in disgust. Then dad said “Well, Tillie, I would guess it has been a while for you. Remember, getting a man is like fishing. It’s all in the bait presentation.” Everyone, including me laughed.

As the night went on, more and more booze went down. The discussion now centered on the “lonely” divorcee. Dad said “Seriously, I know you do not trust men after Hank, but why don’t you find some guy and get laid?” More open mouth blank stares.

She said “I don’t trust men. I am happy with the way I live. Besides, I don’t think I could make myself pick up a man for a one-niter.”

Dad then said, “My son is a virgin (I was 18) and you could teach him whatever way you like it.”

My turn to hide, with a really red face. After the laugh died down, I went to my room and went to sleep.

Next morning, Saturday, Dad got called into work. It was about 10 AM when I went to the kitchen. Mom was making breakfast and she said “I am very sorry that dad said that about you. He had no right, and when he gets home, I will make him apologize.”

“Let’s let it die here and now. I don’t want him to keep bringing it up. Besides, I will have sex when I find the right girl and get married.” This seemed to calm her down, as that’s the way it way it was done when they were young.

The phone rang. Mom answered it and after hanging up, she said “Tillie was so upset at what dad said, she left her car headlights on all night and needs some help getting it running. almanbahis Here are the keys to ours. Get your tools and there are jumpers in the trunk.”

I went there and she met me at the door and said to come in for a moment. She then said “I realized that you were more embarrassed by your dad’s drunken mouth than I was. Are you really a virgin?” I knotted yes. She said “why?”

“The cool girls at school are attracted to the jocks, like the football players. Both the girls and the guys have the IQ of a box of rocks. The girls on my level of intelligence aren’t exactly what guys have wet dreams about, if you get my drift. Besides, for purpose of illustration, let’s just say I got some from a girl. Do you really think I would tell my mom or especially my dad?”

She said “I see your point and understand. Just imagine what you dad would say, even without the booze. (We both groaned) If I were a bit younger, I would be very interested in you, sexually. You are good looking, although a bit skinny, very smart, and seen to tolerate your parents well.” We both laughed.

I said “You have the body that many 18 yr old girls would kill for. (I went with her to the Y and we swam together a few times.) I would take you up on it, if there was an offer made that way.” She kissed me on the cheek and said, “Let’s fix my car.”

The battery was 4 years old and did not respond to being charged. I said “Let’s go get a new one and I will put it in.”

We got a new battery and the car started up right away. She said “come inside. She got out some money to give to me, but I declined it. I said “I need to talk to someone about a problem I have and it’s something I can’t discuss with my parents. Its about sex. Can you imagine talking about sex to my prude mother or mega-mouth dad? Can I discuss my problem with you, if you are good with this? There’s is really nobody else I can go to.”

She takes my hand and leads me to her couch, and she sat on a chair facing me at arm’s length. She said, “go ahead.”

“You know I am good at almost anything I try: school, technical stuff, swimming. That said, one of the “brainy” girls who is just average looking got a bit frisky with me and said something about us getting it on. I guess us nerds are attracted to each other. But being I was not “experienced” I declined because I did not want to embarrass myself, and more so, have that spread around to everyone at school. Get my drift? Do you have any idea of where I can learn about this? I do not want to “get laid” as my friends put it, you know 10 minutes, zip up and go home. I want to learn how to really please a woman and have her WANT to come back for more. I think if I can make them enjoy it, I will enjoy it more.

Being a normally horny 18 yr old, I got semi hard when I was talking, and saw her eyes notice the bulge in my pants. This made me harder.

She took a deep breath and said “I wasn’t ready for that. Let me get a drink and come back. Want a beer?” I knotted yes.

She returned with the drinks, and after a few sips she said, “Would you like me to teach you, and if so, nobody else is to know, I would get run out of town and your mom will kill you.”

I said “You are beautiful. I’ve seen you when we swam, and you really have taken care of yourself. In your case, it’s like polishing a Ferrari and not driving it.”

She and I laughed. She said ” I am beginning to really want to do this. Some rules you must understand and agree with. (I knotted yes) NO falling in love. Either of us, I will tell you what to do and you at least try it. I will not try anything I haven’t tried, or anything my lady friends talk about when we are private. We girls talk about sex also, you know?”

I said “I have overheard some of those conversations. I agree. But why not loving you or vice-versa?”

“In this prudish city, the thought of a 39 yr old woman getting it on with an 18 yr old man would get me jailed or run out of town. I know we are both of the age of consent, but the religious freaks don’t think its right. Cradle robbing they call it.”

I said, “OK when do we start.”

“I’ll call your mom and tell her that in return for fixing my car, I am making you lunch. That will buy us an hour.” And she did that.

After the call, she asked me “Just how much do you know?”

I said “Well, I have some porno magazines, and what my friends say when bragging about doing some girl. However, their accuracy is suspect in my mind.

She said to wait here, and went to her room, bringing back a book of “marital positions” which started out as a biology lesson on the human reproduction system. I said “Just because I am not practicing it, doesn’t mean I don’t know how it works. I had biology in school.”

Next, she went into the foreplay, discussing the kissing, necking and petting, but more so, seeing the reactions of the other person to the act. Something like: listening for the purring and moaning. She said, “The girl will let you know if she likes it, but not almanbahis yeni giriş in words.” Watch for facial expressions and sounds.

I pulled her to me and kissed her on the lips. She moaned and pulled me in tighter. I took the hint and put my hand on her tit. She breaks the kiss and says “you catch on fast.”

When I massaged it and gently played with the nipple, thru her blouse, it became enlarged, and she moaned more. While kissing I ran my hand down slowly toward her pussy. She had on jeans, so I got down there and rubbed her pussy, thru them. She said, “Gently at first.”

Then she put her hand on my crotch and fingered my already hard dick thru my pants. Now we were tongue kissing and getting excited. I slowly started unbuttoning her blouse and she did not stop me. She said “This is important. If the girl stoops you, she is not ready to go on. Do not force her. Just keep doing what you were.”

I got it unbuttoned and off of her. She bent forward as if to say, ‘now the bra.’ I reached behind her and popped the catch. She said, “You practiced this?” I said, “My swim jock has the same catch.”

Now she takes my tee shirt up and over my head. She said, “You are very slim but don’t look bad.” I smiled

I caressed her tits and then started sucking on them. She started squirming and moaning. Said something like “it’s been a long time”. While sucking on them, I moved my hand to her jean zipper, and slid it down. She lifted up a bit so I could get them off easier. I stood up and removed her loafers and jeans. She had on one of the sexy bikini’s my dad gave her. I pointed to them, and she said, “He’s right; they do make me feel younger.”

I busted out laughing and said, “I double dog dare you to tell him.” And we both laughed.

She then reached out and unzipped me. She slid my jeans down and then my boxers. My erect dick sprang out. I was a bit red-faced. She said “You have nothing to be ashamed about. You are bigger than Hank. I think I am going to really enjoy this. Let’s get into it. If you have progressed this far with a girl, she wants it as much and maybe more than you do, we girls have needs, you know. However, still treat her with respect”

She gets up and takes me by the hand to her bedroom. She removed her bikini panties and laid down on the bed face up and pulling me into a kneeling between her spread legs. She was not shaved (it was not as popular back then) but was very neatly manicured. With all her swimming and competition swimsuits being very brief, she mowed the bush as to not show. She guided me down on her and has me finger her out, then abruptly stopped and said, “look at this”. She used two fingers and opened her pussy lips apart and with her other hand pointed out the clitoris. She said, “rub this, as it will give any woman great pleasure.”

I did as she said, and she started moaning and making squealing sounds. She got wet. Then she grabbed a small pillow and put it over her mouth and screamed into it. At the same time, her love juices came out in a flow. This obviously was not covered in biology, so I thought I did something wrong. After she came back down, she kissed me and said “It’s been years since I had an orgasm like that. Thank you.”

She said “Now, I want you in me. Follow my lead.” She positioned my dick over her love tunnel, and said “push it in, gently, all the way.” It slid in easily with her cum to lubricate it as well as my pre-cum, and I was all the way in. I paused to savior the moment, and she said, “You are supposed to push it in and out.”

I said, “I know that, but remember, you just took my virginity and I wanted to savior the moment.” She smiled. Then I started pumping. She said, “Vary the speed and she will let you know what she likes.”

She was tight but not super tight. I lasted about 10 minutes and said, “I don’t have a condom.”

She said “I am already through my change of life. Come in me already….”

I pushed it in all the way, held it there, and shot quite a bit more than I thought I had. This is way better than masturbation. With sex, I mean making love, you are sharing with each other. The way it was meant to be. We lay there in each others arms for a short while and she said, “we better clean up ourselves so you can go home. This is important as you don’t want to have the odor of sex on you in public especially near your father.”

“You can say that again, but please don’t.” We both laughed.

She gave me the book and said “read up on the chapter on ‘oral sex. It’s well written and is from France. DO NOT let your parents find it”

I went home and mom asked, “Where did she take you for lunch?”

“At my favorite Hamburg place on state St.”

She said “I’m glad Tillie and you get along so well” I thought to myself ‘you really don’t want to know’

I read the book over and was wondering if I could go thru with licking a girl “down there”. Then I remembered Tillie’s words “I will not have to do anything that you don’t want to do, but almanbahis giriş these are thing girls enjoy” I resolved myself to try it.

Next Saturday, we got together at her place. She asked if I read the material. I said “yes, but I am a bit squeamish about it, can we take it slow?”

“That was my plan. But first, let’s take a shower together. This is for two reasons: I want to get you into sensuously washing a woman, and to have our ‘private parts’ clean.”

“Let’s go do it.”

We went into her shower, and she had a telephone sprayer which allowed us to very gently soap and wash each other. I told her what I learned about hygiene of that area on a male, and how I was taught in school Phys Ed and how to clean it. She showed me how to clean her pussy area, and to make sure you rinse out ALL the soap. That should have been obvious.

We dried each other off. Needless to say, I was hard, and she stayed a bit wet after repeatedly being dried down there. Ahem…..

She said “Let me go first and take you in my mouth. I have done this before with Hank, but he did not seem to appreciate it. After a few times, I learned to enjoy it. Don’t be afraid to cum in my mouth. Also, you can guide me as to your individual taste, no pun intended.”

She had me sit on the edge of the bed and got down on her knees between my legs. She took my already hard dick into her mouth, slowly, as this was her first time in years doing this. I instantly went into pleasure mode, and she was watching my eyes while sucking me off. She had the whole thing in her mouth, and I just sank into ecstasy, moaned and started breathing rapidly. She knew I was about to cum, and sped up her movements, and I shot ropes into her mouth. After she milked my dry, she let go of it, and she said, “Do you like that?”

I said “Yes”

“Better than what we did yesterday?”

“No, because I was not pleasing you at the same time.”

She got this big smile and said, “Look at it this way: It may be giving me pleasure by giving you pleasure.” I shook my head yes. “OK, your turn. Just do what I tell you to.”


She sat on the bed where I was and leaned back allowing access and at the same time, was able to watch me. She started me by kissing her lips, and working lower, then down to her tits, across her solid tummy to her pussy area. I was instructed to first lick and suck the pussy lips, run my tongue in and out of the love tunnel, and down to the clit which she pointed out last time. She was purring and making squealing noises. After a few moments, she quickly placed a small pillow over her mouth, stiffened up, screamed, and shot some pussy juice out. Not a spray, but a small stream. Her juices coated my face, so I decided to lick some up and taste it. Not bad, a bit salty, but not bad. She said “You just graduated eating pussy”

I said “Till, I enjoyed that a lot, especially because I brought pleasure to you.”

“Some girl is going to get a real prize husband someday with you.” I was all smiles, but must have looked like shit with her and my cum on my face from kissing her, but I was very happy at that point’

She said, “If you read that chapter, did you see the part on 69 where you do each other at the same time?” I shook head as yes.

“Well, it’s going to take a little while before you reload, so we can try that, if you like?”


We cleaned up a bit, she made lunch, and we ate naked, also a new experience. Afterwards, she said “let’s go back upstairs”.

When we got there, she said “Hank only went down on me once and said he did not like that. He wanted to only do missionary, so he was the “leader” and not me. Once I tried mounting him with me on top, called cowgirl, and he pushed me almost off the bed and said not to do that again. It was his attitude and the point about not wanting kids is why I divorced him.”

” I see. Then sex with both of you was almost mechanical?”

“Good choice of words.”

I asked, “so I am the opposite of him, attitude wise?”

“YES, and then some.”

She had me lay on the bed face up. She came over the side and placed her pussy over my mouth, and she moved around until my dick was at her mouth. It was a good fit as we were both about the same height. She said “Put your hands on my hips so you can guide me to wherever you feel comfortable. Then go for it and so will I.”

I guided her to me and tongued her tunnel and licked and sucked on her clit. I was rewarded with a small gush of fluid and lapped it up. I continued to suck/play/rub the clit using my tongue and hands. I remembered the book saying something about a “G” spot inside, and right in back of the clit, so I explored for that spot with two fingers. I knew found it when she let out a muffled scream with my dick in her mouth and got a big gush of fluid. She stopped sucking and said “You read the book alright. Good job, stud.”

She went back to sucking and shortly, I came into her mouth this time, it felt like more came out. We both were licking up each other’s cum and slurping it in. That S O B Hank did not know what he had.

We went into the shower and cleaned each other up, kissing and grabbing as we went along. She said, “What did you tell your mom where you were going today?”

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