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Anal Sex Stories

My Best Friend’s Mom

One of my best friends from high school had gone off to Kansas to play football in college. While there, he began using drugs and got arrested. I would stop by and see his parents from time to time, but when his mom called and said he had gotten arrested, I went right over. I had plans on playing college football at Ohio State but injured my knee, so I went to a local college. I also continued to weight train so I could stay in good shape.

When I arrived at my friend’s parents’ house, his mom was sitting at the kitchen table drinking a beer and I could tell she had been crying. I gave her a hug and asked her what happened. She gave me a beer and told me the story. While she was telling me the story, I realized she had been drinking for some time, as she was slurring her words and not making sense from time to time. She drank three more beers while we were talking; I had two.

Now, she is not a beauty queen, but she is attractive and has a nice body. She has great tits!!! She is the type of woman who has great sex appeal. There is something about her that you can’t put your finger on that makes you want to fuck her. I remember having fantasies about her seducing me in high school and masturbating many nights after being at their and seeing her.

She actually walked in the bathroom one time when was I masturbating at her house—she had been laying out and I could not help myself. I was so embarrassed when she walked in and caught me. I had lubed my cock with Vaseline and was stroking it like a madman. I had just started to come, and when I opened my eyes, she was standing there. I did not know what to say. She smiled and said, “Looks like you are having fun!” I turned red! She said, “Don’t be embarrassed—we all do it!” Then she walked out.

The night of her son’s arrest, she was very worried. I tried to comfort her and we started talking about some of the funny things that had happened over the years. She asked me for another beer; she was pretty drunk. I said there was no more, and she sent me to the basement to get another 12-pack from the fridge. When I came back up, I gave her another beer and she said, “Remember the time I caught you jerking off in my bathroom?” I instantly blushed. She smiled and said, “Don’t be embarrassed. You have a very nice cock. She stood up and walked over to me and said, “You have really put on some muscle this summer. You look great.”

I said, “You look really good, too!”

She ran her hands over my chest and my cock got hard. I was trying to move so she would not see it, as I was wearing gym shorts and it was very obvious. She asked what I was thinking about when she walked in on me playing with myself. I began to stammer. She said that she had had fantasies that it was about her, and that she had fantasized that we had had sex right in bathroom.

Then she sat on my lap and my stiff cock poked her in the leg. She said, “So, it was about me.”

I said, “Yes, I have had many fantasies about you.”

She began to stroke my cock and I asked about her husband. She said, “He is out of town on business. Don’t worry about him.” Then she leaned over and kissed me. Her hand felt so good on my cock, I could not believe this was happening. She stood up and removed her shirt.

I said, “Are sure you want to do this? Your son is one of my best friends and you have been drinking. I don’t want to take advantage of you.”

She said, “I have wanted to fuck you for years!” Her tits popped out and they were beautiful—40D with the most perfect nipples. Her nipples are large, almost double the size of a pencil eraser, round and about one and a half inches long. I grabbed her and started playing with her tits, sucking them and biting at her nipples. She moaned and said, “Harder.” I was sucking like I was breast-feeding. I pulled her shorts off to find she was not wearing any panties. My cock strained against my shorts as she stroked it. She finally freed it and started stroking it. Her hand felt so good I almost came right then.

I pushed her back against the table and helped her up on it. She spread her legs wide and guided me into her pussy. I had to have her. I apologized for lack of foreplay but promised to make it up to her. She laughed and said, “This is just like my fantasies—you can’t stop yourself, you have to take me.”

As I slid my cock in, she let out a deep, throaty moan, which really turned me on. I started with long, slow strokes, letting her feel the entire length of my cock. I told her that her pussy felt good and was really tight and wet. She said, “I have not had sex in nine months.”

I was shocked and said, “I will satisfy you tonight.”

She wrapped her legs around me and pulled me in. I started fucking her hard and fast. She moaned loudly and dug her nails into my back. I pulled out and turned her around so I could see her hot ass. I fucked her doggie-style, as she was bent over the kitchen table. Her tits bounced wildly as I hammered her from behind. Then she started to come!

When she was done, she asked me to stop. She dropped to her knees to suck my cock. Her mouth was better than her pussy. She sucked me for a few minutes, then got up and led me to her bedroom. We started to 69 each other. Her pussy was dripping—the more she sucked the wetter she got. She had another orgasm. She kept sucking my cock. I begged her to stop so I could fuck her some more, but she would not. I shot a huge load in her mouth. She took it all and kept on sucking. I asked her to stop because it was too intense right after coming. She did not stop, but kept on sucking. My cock went limp and she kept on sucking. Then, after about 10 minutes, my cock got stiff again.

She stopped sucking it and rolled over on her stomach. She said, “Take what you want! Use me, I am yours!!!” I paused, trying to figure out what that meant, and then guided myself into her tight, wet slit. She moaned and said, “Fuck me hard.” I jackhammered her pussy. I slipped out and when she was helping me back in, I felt her adjust under me. As I slid in, I felt a lot of resistance. I pushed harder and she let out a deep groan as the head of my cock entered her. She panted, “Slow, slow, please go slowly. Be gentle.”

I slowly kept pushing, fighting the urge to jam my cock in her. Then I realized she had guided me into her ass. I whispered to her, “Thank you, I love your ass and have dreamed of fucking you in it.” She smiled and grimaced as the full length of my cock entered her ass. Her ass was so tight, I was having trouble getting in. It felt like it was trying to keep my cock out. I told her, “Breathe and bear down,” and she did and my cock went deep in her.

She groaned and I asked if she was OK, and she replied, “It hurts and feels good. Just go slow. The only thing I have ever had in my ass is a finger.”

I grabbed some lube and slowly pulled out; her ass gripped my cock like it was trying to hold on to it. She asked what I was doing. I said, “You are so tight I need some lube. It will be better for us both. I lubed her tight, pink rosebud and my cock, and reinserted it, this time a bit faster than the first time. She reared up and yelped and begged me to go slow. I said, “Breathe and bear down, trust me.” I fucked her ass slowly with long, deep strokes, listening as she gasped on the in-stroke and moaned deep in her throat. I whispered in her ear that her ass felt so good and tight. It was like heaven. I told her that it was a dream come true to fuck her ass.

I started stroking faster and harder. She squealed at first and pulled away. I said, “Relax and enjoy. You have to embrace the feeling and the pain will turn to pleasure.” Fucking her ass was euphoric. I was lost in the sensation. The only sounds were her moans and gasps, which turned to sounds of a woman in deep pleasure. I was getting close to coming and started fucking her harder and harder. I tried to control myself, but the feeling was too intense.

She bucked wildly under me. She said, “Fuck me! Come in my ass!”

That took me over the edge. I started drilling her virgin ass. She moaned loudly, yelling, “Fuck me, oh please come, please come in my tight ass. I can’t take much more.” Her begging made me come very fast. I came so much it hurt. I collapsed on her and started to apologize for being too rough. She said no, it was good, that she was just new to this, and the more we did it, the more she’d like it. I asked why she let me fuck her ass and she said, “Your ex-girlfriend was over with Tera, Tom’s girl, and I overheard them talking about how much you like anal sex and how much fun it was.” She had been fingering her ass ever since and fantasizing about me taking her ass.

We continued our affair for the next three years. She got divorced, and her son moved home, which made the affair tougher to hide. He almost caught us several times. Once, he came in just as she had taken a load of cum in the mouth from me, but that is another a story for another time.


MILF Dominance

The first time I experienced anal penetration was with an older woman. She was very dominant, which turns me on. One night she came home with a large bag that I recognized was from the 'toy shop' we like to visit. I started to get wet the instant I saw the bag knowing I was in for a hell of a night. She led me into the bedroom slapping my ass all the way.

"Take you clothes off." she ordered.

I obeyed. Once undressed she took and laid me across her lap. I heard the bag rustle the felt her finger and something cool and slick on my asshole. I instantly tightened up shocked by the sensation. Nobody had ever touched my down there but as she rubbed her lubed fingers around my virgin ass I realized that I liked it. Slowly she worked her fingers inside of me and I was moaning like crazy. This must have turned her on tremendously because I'm usually pretty quiet during sex. She began slapping my ass with her other hand screaming "Do you like that Baby! You want more I'll give you more!" The bag rustled again and i heard the buzz of a vibrator. She pulled out her fingers and spread my ass cheeks apart and I felt the vibrator buzz at my asshole just before she slipped it in. I gasped at the size of it.....didn't she know I'd never had anything back there before? It didn't take long for me to realize it didn't really hurt though. As she worked it in and out, deeper and deeper I became frenzied screaming for her to fuck me hard with it. She was pumping it in and out and slapping my ass bright red screaming "Take it all, Baby. Take all of it!" I came all over her lap, I think she came too. We've found many more anal sex toys and had many more sessions, but none like my first time through the back door.
 


When the wife is away

My wife was away on business in England and I was going to be home alone for a week. My divorced mother-in-law said that she would come over each night after work to make sure I was alright (It was on her way home). I told her it wasn't necessary, but she insisted. The first night she came over, she noticed I was tense and asked why. I told her I had a difficult day at work and that I was fine. She then asked what I could do to relax, to which I replied, "sex would be great, but I guess that's not happening". You have to understand that this was in no way an inappropriate comment considering the relationship I have with my mother-in-law. It was intended to be humorous. However, she responded, "what would you need exactly?". Now, my mother-in-law is a very good-looking 46 year old woman whom I've always found attractive, so this question made me a bit uneasy. I responded somewhat sheepishly, "you know, just to cum". To my shock, she said, "would you like me to do it with my hand?". Within a few moments my pants were down and she was giving me a hand job on the couch. As excited as I was, I couldn't climax and she could see I was getting frustrated. At that point she looked at me and said, "if I let you put it in me, would it speed things up?". Somehow I managed to nod and before I knew it, she was taking off her pants and panties and lying back on the couch. After fingering her for a moment to lube her up I asked if she wanted me to cum on her stomach or if she prefer I get a towel. She laughed and told me not to worry about it. When I asked what she meant, she replied, "just cum inside me, it's not like I'm going to get pregnant." That was all I needed to hear. I plowed into her tight pussy and, after about 15 strokes, blew my wad deep in her cunt. She then got dressed and went home. The next day I got bold and asked if we could do it again and we did. On the third day I asked if I could fuck her in the ass. It took some convincing (I told her that her daughter let me butt-fuck her all the time, which was a complete lie, but, what the hell) but she eventually gave in. After applying generous lube I slid in. To my amazement, she whimpered only slightly as her ass took my whole cock. Being a gentleman, I asked her permission to cum in her ass, to which she agreed. After five minutes, I shot what felt like a gallon of cum deep in her ass. Upon pulling out, I admired my handiwork as my cum slowly began oozing from her gaping asshole. Needless to say, it was a great week. In all, I made six deposits, four in her pussy and two in her ass.
 


Watch This

I am at my mid 20s and my girlfriend's mom is really hot. Every time I visit their house I find her most of the time looking at my crotch. I first suspected her attraction to me when she accidentally bumped her smooth ass to my big member on an occasional Saturday visit. Her husband is kind of nerdish, tall , has thick glasses and very workaholic, maybe that explains why they are so rich.

As I left the house for my occasional Saturday visit, I forgot to check the messages on my answering machine. The message stated that my girlfriend and her dad are off to Hawaii for a vacation. Strangely her mother got left behind. This is the reason for my greatest and best sex in my entire life.

As I parked my car into their garage, i quickly hurried to knock on the door . Her mother answered " You re girlfriend is not here, but if you want you could help me with my household chores?" I hesitated and said yes thinking that who would want to do other s chores for the weekend? I just kept in mind the image of her sexy body which i have been jacking off to when I am horny .

As we proceeded to their living room , I thought to myself that i would make the first move disregarding the thought that this could get my relationship with her daughter ruined or worse i could be sent to jail. As she went to the kitchen to prepare some snacks i quickly unzipped my pants and placed my dick inside the vacuum cleaner and turned it on . The sound which it made gave her the impression that i was vacuuming. With this thought she didn't notice me but naked with a vacuum arousing me. As she placed the snacks onto the table, she then raised her head as i anticipated for her reaction . I was expecting her to be surprised but her reaction was... she just giggled and muttered out the words "Boys and their toys". I became horny as she said " Want me to vacuum you?" I quickly responded with a "hell ,Yeah" She Removed the vacuum from my stiff cock and slowly licked it inch by inch. Then she played with my head , slowly licking and sucking it s tip . Then she swallowed my whole member in three seconds . This is a record for anyone who has been with me the last person who tried it that fast was my girlfriend who gagged.

Then after 3 minutes of intense sucking she knew that i was about to blow and had ti much fun to stop know. She guided me into her room and presented me with her blue dildo and some Vaseline and told me my ass is still virgin, please fuck me hard unlike my stupid husband. I quickly nodded and was turned on to the fact that i was about to fuck a virgin. I slicked the dildo with Vaseline and inserted it into her tight ass. She moaned as i pressed harder and deeper . Then i removed the dildo and was begged to be filled in . Then i made her bend . Then i inserted my stiff cock into her with one thrust. This made her scream . I pounded her hard , harder and harder as she inserted the dildo inside her clit . I then moaned " Dian ,I m about to come" she then responded let me swallow your seed . I pulled out of her and let her joyfully suck my lollipop . I moaned "OOOH DIAN YOU BITCH" this turned her on and swallowed me dry .We didn't realize that we were on cameras , a part of their security system. Its a good thing that i saw a hidden camera and questioned her about it or we might end up dead. I asked if i could keep the tape and she gave a condition that we would do this at least ounce month....... Know as i stroke myself as i rewatch our flick i asked myself did i really love Marge for herself or her mother?


Older Anal Virgin

My first experience was a few months ago when at 51. I was dating a 29-year-old man. My lover had guided me back from a dry period following the break up of a long marriage. It was an incredible turn on for me to have this young virile guy so attracted to an older woman. I had never had anal sex but was curious. He was experienced and willing to be very patient. I worried about the "mess". He assured me it would be fine.

We started with anal play and touching during our lovemaking sessions. He applied gentle pressure and circling motions. One night when I decided I was ready for more, we started with vaginal fucking, doggie style. He did the usual anal stimulation, then applied lube to a butt plug. He gently and slowly inserted the plug into my ass, advancing it slowly as I relaxed. After I became accustomed to the feeling of his gentle thrusting he asked me if I wanted him to put his cock in my ass. I was more than ready for that! He removed the butt plug and showed me that it indeed was clean.

He lubed his cock and slowly inserted just the head at first. At the same time he inserted a small vibrator into my pussy and positioned one hand where he could finger my clit. He moved slowly until his cock was completely inside me, then pulled back and began to gently thrust. I was surprised to hear moans from myself in a pitch I have never before uttered, deep throaty sounds. It was the most incredible feeling I have ever experienced with sex.

He continued to ask if I was alright and whispered sex talk in my ear while thrusting. It was difficult for me to talk but between gasping breaths I got the message across that I wanted him to fuck me hard. I pushed back into him and he used his free hand to hold my hip as he pulled me to him. I came before he did but continued to enjoy the experience as he spoke into my ear describing what it felt like to him...eventually asking me if I wanted him to come inside me before he filled my ass with his sperm. I can still remember how it felt as he tensed and shot his load deep inside me.


European Vacation

I was in Europe meeting a more mature lady of 34 (I was 24) and we were at it nonstop. One moment sticks in my mind: when I had just finished a shower I walked back into the bedroom and she was on all fours on the bed. Naturally I mounted her and slid into her waiting wet pussy from behind and banged away with her window open for the neighbours to see in the apartment opposite screaming for me to fuck her cunt harder. Shortly afterwards I was laying on top of her and wanting to fuck her again. She said she wondered if I was going to fuck her up the butt when I came out of the shower. That was magic to my ears. I love giving a girl a good hard fucking up her arse. So I fed my cock in her pussy to get it nice and wet, then pulled out and nudged it against her anus. With a little force I slowly entered her. Mmmm, sweet. I pumped her tight brown eye until I shot my load deep inside her cavity. She was one horny fucker. She loved taking a load of my spunk in her mouth and she said she swallowed, but she continually spat it out into her sodden g-string. This lady could also deep throat so I once tried shooting my load when my helmet was firmly deep in her throat. I got a shot off and she pulled away for air. God, I wanted to pump it all in. Fuck, I hope my girl now takes it up the ring piece. I know she swallows.

Anal Sex | Neighbor | School and Work | Mother-in-Law | Step-Mom | Friend's Mom | Masturbation

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