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- True Sex Confessions -
Straight Male / 18

Friends Mom Pushed Me Over The Edge

Yesterday I was at my friends house hanging out at their pool. It was around 2pm when he got called in to work. He said to stay and enjoy the pool and he should be back from work around 10pm. It was around 4 pm when his mom came home and came out to the pool. We were both surprised to see each other. After our hellos she laid on the pool chair next to me. She had on a thong bikini and her breast were almost popping out her top. As she laid on her stomach I couldn’t help but stair at her nice ass. After she caught me looking she spread her legs just a little. I could now see a little of her pussy lips because the thong didn’t cover much.
My cock was getting really hard in my bathing trunks. After a while she asked if I would rub some sunscreen on her. As I started she reached back and in did her bikini top but I couldn’t see much because she was still laying down . After rubbing some all over her back I moved to her legs. After finishing her legs she said “ you forgot my butt, I don’t want my butt to burn”. I squirted some on her ass and started massaging it in. Her ass felt great. I took my time hoping it would last. Not sure how but I got a little braver and slowly ran my hand down her butt down to the side of her leg just barley brushing her pussy lip. She moaned and squirmed a bit then said “ wow that was dangerously close” . After a min or two I did the same thing this time clearly running one a part of my hand down the center. Again she moaned but this time spread her legs more.
I did this a few more time each time causing her to moan in pleasure. Just when I thought I’d get really brave And try and rub her pussy she turned over onto her back. I rubbed some sunscreen on the tops of her legs then her stomach. Then she removed her top and and said “ you think you can rub some on my tits with out saying a word to anyone that you did?” I think I mumbled yes. Her breast felt great as I massaged sunscreen on then. She started to moan as I did so. I then got really brave and squeezed some on one hand and started to rub lotion under her thong I moved in over the center of her hips and with one finger I pushed down splitting her pussy lips in half. I instantly felt the wet warmth of her pussy. My finger slipped inside her. She jumped a bit and said “ fuck what are you doing. That’s a little too far baby . I can’t let you fuck me.” Even though she said that she didn’t stop me so I kept going .
I couldn’t believe what was going on and she was letting me do this. I was 18 and had never been with a woman to this point . All I knew about fucking a girl was what I had seen in magazines and porn flicks. My dick was so hard that it hurt. After about 10 min of massaging her pussy she put her hand over mine and had me put 2 fingers inside her. She started to rub the top of her pussy as I finger fucked her with 2 fingers. It wasn’t long before she cried out she was cumming .
After it was over she turned and laid on her stomach again. As she laid their she said” OMG that felt great. Thank you. You know I can’t let you fuck me but if you promise not to say anything to anyone I’ll let you finger me and feel me off any time you want.” I just said sure I won’t say a word and then stated to massage more lotion on her ass and over her pussy . I moved her thong to one side and again I started to finger her pussy. She moaned loudly. I moved over her and as she was face down not looking I pulled my cock out of my loose swim trunks and with one hand I stroked my rock hard cock and finger her pussy with the other hand. Then not really thinking I couldn’t take my eyes off her pussy and then a sexual rage came over me. I positioned my cock at her entrance and with one hard thrust I buried my cock all the way deep in her pussy.
She cried out “ OMG FUCK ! Your cock’s in my pussy . Fuck what are you doing ?” I said ‘fuck Mrs Johnson I could take it anymore. Ive never felt a pussy before I just had to know what it felt like to have my dick inside you” . She looked back surprised and said “ OMG I’m your first” ? I just said yes as I stayed buried inside her. She said OMG Don’t you dare say a word to anyone. Ok baby do want you want with me. Make yourself feel good . Fuck my pussy. “ I started to pump her pussy sliding in and out and pushing in deep at the end of each stroke. Before I knew it I grab her ass tight and thrust hard inside her and cry out AHHHH !
I start to shoot stream after stream of cum inside her. It almost felt like I was peeing inside her. It felt like I shot forever filling her pussy with my cum. I looked as I watched cum squeezing out from around my cock in her pussy. It all felt so warm, wet and slippery. She cried out “OMG you came inside me . Fuck that’s not good you need to give me warning and pull out.” She turned over and looked at her pussy saying fuck that a lot of cum. She then grabbed my cock and started sucking it. I can’t even explain how good that felt but I was soon hard again and fucking her again with me on top of her. This time I lasted a little longer. Just before I was about to cum she cried out she was cumming and her body shook all over. This freaked me out a bit but she was still shaking I shot another load of cum deep inside her again. Again it felt like I shot for ever. I was squeezing hard trying to shoot as much as I could. Again she cried out “fuck you did it again. You came inside me. Fuck I’m not on the pill”. We fucked 2 more times before I left each time I shot my cum inside her.
Before leaving she kissed and said if you keep your mouth shut about this you can fuck me any time want. But I’m going to have to go on the pill. I have never known anyone shoot so much cum. I love it.
This all happened yesterday! I can’t wait till this coming Saturday when my friend has to work. I get a hard on just thinking about yesterday. She will not text me but she called today saying how much she enjoyed yesterday and if I was still ok about the whole thing. I told her I was more then ok and couldn’t wait to fill her pussy again. She replied “well that’s not the only hole your going to fill”.

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# 46858 - by John / August 10, 2020
- Women Only -
Straight Female / 29

I Like Being The Pussy In The Relationship

Being a home schooled brat I had never been around men other than my father, my mother was a very dominant woman and my father hid away at work. They got divorced when I was ten. When I was twelve my mother slapped me with her bare hand between my legs. She told me I wasn't born with balls but I had to grow a pair. Men were bullies but once they understood who wore the pants they sniffled and got out of the way, a necessary evil.

I was nineteen when I caught my mother eating out a secretary from her office. They were in the living room, the secretary on the couch with her legs wide apart and my mother on her knees with her face in her pussy. It didn't surprise me.

After college I went to work for Caterpillar in Cleveland. I got manhandled by a very dominant man. He fucked me. No permission required, he wanted me and he had me. I had never been around a dominant man like that and he fucked me pretty much whenever he wanted. He gave me instructions to keep coffee for him in my apartment, and beer. I also kept changes of clothes for him. He asked for a key to my apartment and he came over at all hours of the night.

My mother met him after a year and she wrote me off, told me that I was a pussy and that man was going to fuck me until he got tired of me. By then my mother was living with a woman she had met at a lawyer's convention. That first meeting my man friend put it over on her, she got mad and left.

I made up my mind that for me I wanted a man who wore the pants, I liked being the pussy. I guess I took after my father. The man I married is that kind of man.

1
# 46862 - by Carla / August 10, 2020
- Dating Disasters -
Straight Female / 31

Finally

I found out my fiancé was cheating on me and broke of our engagement. I was heartbroken but, through some friends encouragement, I finally got it through my head that I’m a young, 31, fit and attractive little blonde girl that men covet and it was time to put myself out there. I went on a few dates but they weren’t interesting at all. In fact, one guy was cute and I’d decided to sleep with him because I’d gone so long with out sex and just needed to scratch that itch. He turned out to be so lame and such a whiny millennial that I just lost interest and cut the date short. So fast forward to a month ago. I went out after work with a couple of single girlfriends and we were having fun, laughing and being silly when a guy started talking to one of my friends. She ambled off with him and my other friend excused herself to go outside and make a call.

So, now sitting by myself I suddenly felt like a fool and was getting my things together to leave when a tall, good looking dark haired guy walked up and asked how the prettiest girl got left alone. I smiled and said it was just my luck. He asked if he could get me a drink and I thought “Well he’s cute enough” and said sure. We walked over to the bar and ordered two beers, for which he paid, and we began chatting. It started well enough and he seemed fairly smart. Soon though it became clear he was kind of douchey because he kept looking at himself in the mirror and at one point asked me if I was looking to play tonight or a relationship.

I was a little surprised at his directness but said probably a relationship. He then said “Good to know, I have to honest, you are sexy as shit and your body is rock hard but if we went home and fucked tonight I know exactly what would happen”. I said”Ok, goofball I’ll bite. What would happen?” He said “ you’d fall madly in love with my cock and I’d never get rid of you without a bunch of crying” I laughed out loud And said “ Worst line ever. You are the king of the douchebags”

Things work out the way they do and about an hour later I was naked in his bed kissing him. I was so horny I just decided to hell with it and his idiot charm won me over. He had gotten pretty drunk and while we were kissing I wrapped my hand around his cock and it was indeed very, very big but not very hard. I was afraid he was going to be too drunk to perform but he slid down between my legs and began earnestly licking my pussy. I was a bit embarrassed and I don’t think he even noticed that I came almost immediately. I had been so long since I’d been touched and when his tongue circled my clit I just let go. He finally rose up and kissed me without wiping his face and I could taste myself all over his mouth. It turned me on somewhat but not nearly as much as when he pushed his now rock hard monstrous dick inside of me. I gasped and before I could stop myself said “ Oh god”. He said “it’s a good dick isn’t it baby? Damn your pussy is tight and juicy” He began gently but after a couple of moments he began biting a5 my left nipple and pounding me harder. For several seconds every time he thrust his huge dick inside of me I lost my breath and I was afraid I was going to pass out. My ex wasn’t small but nothing like this guys. He finally let my nipple go and put his mouth right by my ear and repeated over and over “ Fuck baby your pussy is so good”. I got into rhythm and felt like I was enjoying it but the I began to think he was going to be drunk to cum and I’d wouldn’t be able to take this kind of pounding all night. I whispered in his ear “Cum on my belly for me baby”. He moaned loudly and just started hammering into me. My legs were spread as wide as they would go and I could hear the suction of his huge dick pulling in and then thrusting back inside of me and his balls slamming into my ass. This went on for a long time until he finally said quietly in my ear “I need this nut so bad baby”. He then slid his right hand under my ass and began pulling it into him as he thrust deep, deep inside of me. Suddenly his middle finger slid partially into my asshole and I gasped but the felt an incredible sensation and before I even realized what was happening I began screaming and cumming so hard that I lost control of my bladder and began peeing which felt like total release and my orgasm peaked while I was screaming and begging. Rather than grossing him out he seemed to ge5 more excited and roared “Take my nut, take my nut you fucking hot c**t” and I felt his dick just explode warm goo at the base of my vaginal wall deep inside me. I felt three distant hard squirts of his cum inside of me while he was buried fully and screaming “ Oh fuck” over and over. He then pulled out of me squeezing his dick hard and put it on my lips. By this time I was just so completely depleted I just let him and opened my mouth and began sucking on his huge cock head. Incredibly enough he just kept cumming and as I had no room to let it dribble out I just started swallowing and he said “ Oh my god” and I must have swallowed four full mouthfuls of his cum. He pulled out and I gasped for air and we both started laughing. He said “Ok, all bullshit aside that was my favorite fuck ever. Tell me you’ve had better? I admitted it was pretty awesome. He grabbed me and pulled me into him which, though I was gooey,sweaty and stinky felt very good. I stayed there until he started snoring and I got up on very wobbly legs and peed. I considered staying the night with him but while I was in his bathroom I heard him fart loudly and when I went back in the room it stank badly. Nota big deal in a relationship but all in all I decided it was time to leave as I began to feel a bit whorrish.

So I’ve talked to him a couple of times on the phone and it appears like my vagina is actually causing the attachment although I will admit masterbating thinking about that big cock a couple times. My girlfriends tease my that I got “dick down” very well. I’d never even heard that but does describe what happened pretty well.

Why was this date a disaster. Well, because I have been on three dates and fucked one guy since my ex moved out. Admittedly a great fuck but today I found out for certain that big “dick down” I got impregnated me. One fuck and I’m pregnant. WTF. Of course studly wants to marry me and start a family. God. Though maybe not the worst to have that dick to come home to every night. Big eye roll.

3
# 46823 - by Sofunone / August 7, 2020
- Fetishes and Kinky Sex -
Straight Male / 22

Found A Friend's Mom Online

I ran across a good friend's mom naked online a few days ago. She's late 40s and a BBW, but pretty face and has always been friendly. She always treated me like I was one of her kids when I was at their house. I used to jerk off to her, and tried to catch peeks but never could. Best I ever got was sniffing her panties when I went to the bathroom.
She and her husband are posting her naked and blacking out her face, but I know its her. She's been shared with another guy once and fooled around with women, and I'm learning about all kinds of kinky shit they've done.

They're not looking for anybody right now, and I know she'd never go for me because she's known me since I was like 13, but I really want to fuck her more than ever now.

Any advice on how to get them to let me fuck her?

4
# 46806 - by Nick / August 5, 2020
- If The Boss Only Knew -
Straight Male / 36

Several years ago when Craig's List was good for random hookups, I had a pretty hot encounter at my job in New York City.

I worked in a small office that had two companies on each floor, which were separated by a long hallway. My office was on the 8th floor.

One Friday afternoon, my boss was in meetings all day and the other two people were out all day.

I learned about Craig's List and started checking it out. I think it was called Casual Encounters (?)

I posted about being in my office alone and looking for someone to come and make out.

I got a response and we started emailing back and forth.

She said she had one other guy she was about to go meet but he hadn't heard back from him. So if she didn't hear from him in the next 5 minutes she would come meet me.

My cock was hard just thinking about this potential situation. Here I was alone in the office with a possibility that a co-worker could come back in trying to have this girl come in and hook up.

She emailed me back saying she would come to me. I asked what she looked like but all she said was guys never complained about her. I thought that was a bad sign but I said to myself, Fuck it, see what happens and even if she's not good looking, the experience could be great.

So I'm waiting for the buzzer to ring and my dicks getting hard in anticipation. The buzzer sounds, I buz to let her in. I stand in the hallway waiting for the elevator and she comes out.

She was ok looking, a little chubby, glasses and wearing like a hippy dress but she had really big tits.

She came in and I closed and locked the door. She sat down and we started talking a little bit. Then I just leaned over towards her and started kissing her. We made out and eventually stood up.

I gently moved her over to the wall next to the door and thought, Holy shot, someone could come back to the office and here I am making out with some random girl in the office. It excited me even more.

We were really going at it passionately and I pulled up her dress and pulled her panties down and started fingering her. At that point she unbuckled my belt, pulled my pants down and started blowing me while I continued to finger her wet pussy.

So I'm standing against the wall and she is bent over getting fingered while giving me the most amazing blowjob.

She stops for a second and let's put this little squeaky moan and says Oh fuck, im Cumming! She grips my ass and then continues sucking my cock. Im so fucking hard, I say, But m gonna cum thinking she may just stop and jerk me off but she keeps going and I shoot my load in her mouth. I put my head back against the wall and try to catch my breath.

She pulls up her panties and asks where the bathroom is.

She comes out, I walk her to the elevator and tell her how amazing that was. She gives me a quick kiss and says goodbye.

We emailed a few times after that but soon after I got a girlfriend and I never saw her again.

I have such great memories of that exciting office blowjob and I never looked at that wall in the office the same way again.

If the boss only knew....



0
# 34601 - by Anonymous / March 17, 2017
- I Did It For The Money -
Straight Male / 40

When I was 20 I got to know an older (40) female barber (Kim) who had a great pair of double 'D' tits. Although she was older than me, I fantasized about her, mainly because of her tits. I waited for her in the parking lot and asked her out, but she refused. I kept coming to her to cut my hair though. About 6 months later I asked her to help me watch a friends house who was out of town. She surprised me and agreed. We fucked four times that night on my friends bed. Kim and I maintained the relationship and I went to her apartment once a week for sex. She would buy me small things and sometimes offered me money for the sex. I recall walking around the fair ground with her one time and meeting one of her friends, who thought I was her son. It didn't matter to me as I was getting pussy, with some great tits. The relationship finally ended when I met another girl, who I thought to be faithful to. Still wish I maintained some relationship with Kim though. There were a couple of nights where I could have used a good lay.

1
# 17709 - by Anonymous / December 21, 2013
- I Did It For The Money -
Straight Female / 31

I've a 31 year-old married woman from a middle class family. I put myself through college first by waitressing, then as a shot girl in a shitty strip joint, then as a dancer in that same shitty strip joint, then as an "entertainer" in a high end club where I started having sex with customers in the cr. After awhile, I met a man who convinced me I could make a lot more money with less effort as an escort. I joined an agency and did pretty well. I was very cute and innocent looking and had a knack for making older men feel comfortable enough to relax and perform. My rates were high so I was blessed with a high end clientele from which I had a high rate of repeat customers.

Escorting started out exciting (I was so nervous the first few weeks) and after awhile I got to know the men and their likes and dislikes so well it became pretty mundane. I was good at it and worked to stay fresh so I kept pretty busy for a couple of years. I got used to the sex though (really appreciating the older men I was with who were far more unselfish than men my own age were) and graduated not owing any money and actually had managed to save some cash.

I got out of the business after graduation and ended up working outside my field in a law office specializing in disability. I got out clean. Nobody I knew had any idea other than that I had worked as a waitress and was very frugal in saving my tips. I met, dated and married a wonderful man and had two kids and now I work on appeals briefs part-time. My kids are now in day-care and pre-school.

Late last Summer, I did something stupid. We were hurting for money. With me only working part time and my husband being under employed, things were getting tough. I talked with my husband about my taking on more work which he was thrilled about. Unfortunately, there wasn't any real work out there where I could make decent money. I started thinking of those envelopes of crisp hundreds left on hotel dressers by those attentive and tender men who paid my way through school. The more I thought about it, the more I seriously considered calling my old agency. I knew I wasn't the cute innocent college girl I had been but I also knew that there was a market for attractive women my age. I called my old boss and talked with him at length. He was pretty eager for me to start up again as I had been a good earner. Just before Labor Day, I decided to let him post my profile and see what happens. I went in for the photos, signed on and waited for my first call. I was very worried that someone would find out. Escorting was a part of my past that no one knew anything about. I knew I was taking a huge risk but to be honest, It wasn't just about the money. I missed the attention as well. I love my husband but no one man can give a woman the varied attention I got from my many clients. I found I really missed it. I was stupid but I did it anyway.

Things went well. My clients are younger than they used to be mostly being married men in their thirties and forties who either aren't getting the attention they need at home or their wives have let themselves go and they want a thrilling experience with a well put together woman who doesn't say no to their desires.

This time the experience has been different for me as well. I find myself giving more attention to the clients and they less to me. I still enjoy it as my sexual tastes have evolved. I don't have to work as hard and be as patient because these men tend to get it up and keep it up and tend to really take charge. Some of these men have introduced me to some really rough sex which I've found I enjoy tremendously. My husband is a pretty pedestrian lover who I enjoy but the different types of desires my clients seek has opened me to a whole new sexual world.

Several men have paid me far above my regular rate to take part in things like bondage sessions, girl on girl sessions (including one man who paid me a thousand dollars to seduce his unsuspecting wife and have sex with her while he watched which was a great experience when it all worked out) and public sex and some want me to do more, a lot more.

Men are offering me large sums of money to spend weekends with them, to engage in group sex with them, to go to gang bang parties with them, to pose as their wives for swinger activities and one wants me to go on vacation with him for a week at a sex resort. He is a wealthy single man who enjoys have sex with married women. I am attractive enough to ensure that we'd be very popular at the resort and he'd be able to use me to hook up with the couples he's interested in.

I am very tempted by these offers. I could make a huge amount of money if I were to expand my services into these areas. I am still a very talented escort. I'm seriously considering taking up some of these men on their offers but I'm not sure how to proceed. How do I explain my absence from home to my husband?? How do I explain the money?? How do I cover my tracks?? I'm afraid it'll just be a matter of time before I slip up and I lose him and our life together. The escort life is only fun because I have a real life to balance it against. I like my real life better and don't want to lose it but I don't want to give up the opportunities escorting is giving right now. These opportunities won't be here much longer. I really want to take advantage of them now while I still can but I don't want to mess up my life.


3
# 14069 - by Anonymous / April 3, 2013
- I Did It For The Money -

I am a happily married woman but I have a dark secret, I recently got a sugar daddy. I love the idea of getting fucked in exchange for cash. A few nights ago I let him fuck me and got $500 out of it. I was so horny that I squirted on his couch as he fucked me from behind. My pussy still throbs at the thought. I am now considering getting a second one.
Husband doesn't know and hopefully I can keep it that way.

2
# 12627 - by Anonymous / November 15, 2012
- When I Was A Kid -
Straight Male / 53

I'm a guy 73 years old and this happened when I was 13 in the 8th grade. 1958 59 school year and my group was first half of the day in homeroom. Reading English spelling and such. Afternoon was shop PE music/art and science moved from class room to class room. The others did the flip. We all had lunch together.

One day I finished lunch quickly and was playing catch with a friend and he didn't catch the ball. It went through the olenders headge stopped next to the science building. It's a modular building located between the play field and the teachers parking lot. There's only one way into the path between the hedge and the building. The maintenance man said I could go in and get the ball with the couches permission.

I got permission and went in. Found the ball and started back out and looking into the window and there's Mr C and one of the 8th grade girls. Now Mr C Is about 6 foot 6 inches tall and 265 pounds. Hugh hands and the longest fingers I've ever seen. The girl is Penny laying on the teachers desk naked while his middle finger is going into and out of her pussy. I can't believe I'm seeing him finger fucking her during lunch hour.

I set with her on the bus on the way home and let her know what I saw. I asked if she's ok with him doing this or does he have something on her. She said she loves it and ask me not to say anything to anyone. I agree then she tells me that when she's baby sitting for them most times on the way taking her home after she lets him fuck her in the seat of his truck. I have never told anyone until now.

0
# 45436 - by Anonymous / July 25, 2019
- When I Was A Kid -
Straight Female / 50

My mother worked at a car dealership, she was a single mom 34 and more or less OK to look at, but she had a hard thing about her and she didn't have a boyfriend. I was 16 and going through all that stuff. The head of the maintenance department had a thing for my mom and she complained about him all the time. More than once he had tried to get into her pants and she kept herself on the other side of the table whenever they were in a room together.

So it was Saturday and a friend of mine and I went to see Jaws for the first time. We were in line, it was such a hot movie that people stood in line for a couple of hours to get in. The man from the dealership bought his ticket and saw me in line and asked to break in. He just broke in and told the people in the line that I was his daughter. In the movie he sat beside me and bought us popcorn and drinks and when the movie started he took my hand and he just wouldn't let it go. My friend kept hitting my shoulder asking what the deal was and all I could do was shrug. As the movie went on and the scary parts happened I grabbed onto his forearm. When we left the theater his arm was gashed and bleeding where I had stuck my fingernails into him.

He took me to the little boy's room and told the guy in there to leave and he locked the door (it was my first time in a boy's bathroom and the first time I saw a urinal, which is a whole different story) and he had me wash his arm with soap and water and dry it with the towel (in those days there weren't paper towels or hand blowers, just a towel on a roller). After I had finished doing what he told me he said he wanted a kiss, and not a stupid girl kiss, he wanted a real kiss and he grabbed me and took my behind into his hands and pressed me up against him and kissed me on the mouth. After a minute or two he released me a little and used one free hand to grab my boobs and tell me that as far as he was concerned I was all woman and I was ready. Ready for what? He turned me around and told me to hold onto the sink got my pants down and he screwed me on my tiptoes.

Well that was the way you lost your virginity in those days, some girls lost it in the back of the car, or under the bleachers, or out behind the basketball court, and I lost it in the boy's bathroom at the movie theater. To me it was glorious, it was so glorious that the first thing I told my girlfriend when I walked out of the boy's bathroom is that I had lost my cherry. She wasn't good at secrets and one person to another it wasn't long before the word got back to my mother. When she confronted me with it I had to confess who it was. Well that was the end of it. Except for one detail, he could have her fired, so she kept her mouth shut. But from then on when he grabbed onto her she let him, when he pushed over the table in his office she let him, when he came to the house for dinner which she now fixed for him and he took her back into the bedroom she let him. Anything for him not to go after me again.

He never grabbed me like that again, but he sure wanted to. He would call me over to talk to me and he would send his eyes up and down me, stop at my chest and stop at my crotch. He liked my crotch because he looked at my crotch all the time. If my mother caught him she would slap him and tell him to look at her. As for me, I liked him looking at me like that and did everything I could to give him something to look at.

2
# 45535 - by Anonymous / August 2, 2019
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