We've all had them - those truly hateful embarrassing moments, caught with your finger up your nose, or snooping through a medicine cabinet, sneezing snot all over a fellow passenger, or realizing you forgot to set the parking brake after your car rolls into a gully, or needing to wrap your jacket around your waist when your period unexpectedly started when you were wearing white pants. This is the place to chronicle those most embarrassing moments so we can laugh at it together. Let the whole world know your bad habits and when you got caught committing them.

All Intimacy Exposed I Became His Office Romance, His Baby

My job was Benefits and we were evaluating a new health insurance provider. It was me, the rep, and my fifty year old boss. During his presentation he offered an example. Looking at me he said 'height', I said 'five eight', he said 'weight', I said 'one thirty'. He looked at, 'come on, weight?' I looked at my boss and still looking in his eyes I said 'one forty two'. Other questions about my medical history, my reproductive status, all the questions you answer on a form, but never out loud.

He gave us a sample quote, we went over the deductible options, copays, etc. We then went over the staffing, males, females. Any known problems, if not declared you lose cover. He left, I sat there, my personal health and intimate life exposed to my boss.

He stood, walked over to me, leaned over and kissed me. 'I think you should get pregnant, a couple of kids, a couple of years at home with kids, work out, move into a real house, get married'. He kissed me again, this time a long kiss.

All personal space was gone, forever. He told me to kick the habit, quit birth control completely. All those hormones affect you.

After six months, I was by then totally under his gaze and influence, kissed on the mouth everyday, in front of any coworker present. I had a pet name, and Baby. Everyday when he kissed me he told me he loved me.

It was Thanksgiving and my mother was in the hospital, thanks to a gall bladder operation. He asked me to have dinner with them, after asking my mother. At the table he announced to his wife and daughters, I was going to have his babies. It caught me totally by surprise, shocked his wife and daughters. 'She's family', and that was the end of discussion.

I did get pregnant between Thanksgiving and Christmas. On purpose. What can be more intimate than surrendering yourself to be made pregnant. He helped my mother move to a new house, with washer and dryer, I had two kids and stayed home with them. I don't use hormone based birth control, I only use rhythm.

I'm not married, not by the church, or according to the vital statistics. I'm sort of a concubine or common law wife, is what the family law lawyer tells us. I'm free to use his name, and say I'm married. I technically still work full time from home. He claims me and the kids as his dependents, both for insurance and tax purposes. I weigh one fifty three, I have not been able to drop down to one forty.

My mother likes him and she gets along quite well with his wife now. She calls me her daughter in law. And my intimacy is total, nothing about me is hidden or kept from him. Including me.

  • Big Rob

    I’m a 29 year-old male married to my 27-year-old wife. I’m a reasonably fit man, but my wife is a little on the chubby side. She has nice big titties a bit of a belly that I absolutely love and thick thighs to keep my ears warm. We’ve been trying to have a baby for the last three months. Having sex all the time, but nothing has happened. Three days ago she started her period again and she was heartbroken.

    I told her we had to come up with a different game plan and I would do anything I had to to make this happen for. She wanted a baby bad. We talked about it and decided our next step was to see a fertility doctor.

    Last night she came home a little late, told me she had been at my parents house on the way home from work. She put a box of condoms on the table, and told me my dad, or Big Rob as she now calls him, Said I needed to start using these. He told her it’s best if I use condom so we knew for sure who bothered the baby. She told me she would never deny me of sex when I wanted it, but I had to use a condom until she was pregnant and that she may be a little messy if I want it as soon as she gets home.

    I have no idea what brought all this on, like I said I thought we were going to see a doctor. Apparently, her and my father have a different idea.

    I have to be honest I’m pretty upset over this. This is something they came up with on their own and never talk to me about it. I have no idea if my mother knows anything about it or not.

    I don’t even know if this is something I can agree to. Wearing a condom when I’m married seems a little ridiculous.

    We Thought We Were Home Alone

    My boyfriend wanted a quickie one evening before work. I’m obviously not gonna say no to sex so I told him to come over because my parents were out for the next few hours

    So he comes over. I start with a bj as usual then he pulls my shirt off and just pulls my panties to the side. It was that time of the month so it was an anal sex day. I had lube laying beside me. I put some on my butthole and put some on his dick

    He slipped into my butt and started to fuck me. He’s getting into a good rhythm and I’m rubbing my clit at the same time. I enjoy anal

    We were having sex in the living room. I figured it was a quickie so we could knock it out there real quick.

    Things are feeling good and he’s definitely getting close when my parents walk in!

    Both my mom and dad saw my boyfriend’s dick in my butt and a tampon string hanging out of my pussy. It must had pushed my boyfriend over the edge getting caught because he started to cum and he wasn’t going to pull out when cumming

    Both my parents stood in shock and my dad turned around and walked back out into the garage. My mom didn’t seemed phased at all. My mom grabbed a few tissues and handed them to my boyfriend. She told him to clean up and get dressed

    Then as he pulled out my mom grilled us for not using a towel on the couch when having sex. I told her of all things your worried about a towel. She said hell yes I don’t want pussy juice or cum on my furniture.

    My boyfriend left saying he’d text me later. I put my panties back on then my jeans. As I getting dressed my mom says so anal sex while on your period? I told her obviously you saw where his dick was. My mom told me I let your dad do the same thing

    I instantly said gross don’t tell me that. Then my mom said well I just saw a guy cum in my daughters butthole

  • Masturbating Turned Into Questions

    Oddly I have a masturbation schedule. I masturbate on Saturday but in addition to playing with my dick I use a prostate massager. Love the feel of a prostate massage and it’s good for the prostate

    So Saturday comes and my dick is very hard and ready to be played with.

    I put my prostate massager in my butt and look up some porn. There are a few videos that always make me cum quick.

    I’m naked on my bed and my dick is very hairy as I haven’t groomed my pubes in years. I’m working my prostate massager and stroking my dick. I cummed. A big load as usual. It’s all over my pubes and some on my belly button area

    Then my mom opens the door. Yes I live at home. I guess knocking isn’t a thing. I stand up right away. Very obvious I cum all over my pubic hair and my dick is still semi hard. And I still had my massager in my butt

    The conversation that came about was extremely awkward and embarrassing. Especially since I pulled my massager out of my butt then my mom asked if I was gay. I told her no it’s a prostate massager which is good for prostate health

    I’m standing there naked with cum on my bush when she turns around and leaves

    Now What

    Ok so I started teaching at 23 private school taught math and Spanish. I’m short 5 foot 1 120 lbs stay fit had horny 8th graders falling all over me laughed it off not paying attention to them brushing it off. Fast forward 10 years and I’m single again and out with friends and we run into a few guys at the bar. The seem young they are in there early 20s. One kept on me and my friend says why don’t I go for it who cares. You’ll never see him again you could use it. Think about it and say ok what ever happens happens. A bit goes by I end up back at his apartment he fucks me. Good sized dick outs it to me leaves me limp and asleep. I wake up in the morning I’m naked he’s naked he’s hard as a rock I climbed back on rode him to a massive orgasm. He says I want to cum in your mouth I get off lol literally and I am laying down on my stomach giving him a bj and jerking at the same time. I’m proud of my bj skills really messy and have never had any problems with my technique. As he gets ready to cum he grabs my head forcefully holds it on my mouth shoots a load and I try and swallow as much as I can. A few dribbles leak out I lick them up clean his balls he keeps telling me I’m a good girl and for some reason it’s working because I’m sucking his balls clean. Then I look up at him and he tells me. Fuck that was great MissC. He called me what my students call me. He tells me his name and it hits me I was his 8th grade teacher. I’m naked with his balls in my mouth. I stop started to get dressed legs shaky candle find my panties put my skirt and blouse on. Bra is in my purse. He says can we hook up again soon. I’m torn it was good I say text me and go to walk out his room. His roommate was in the living area and he was also an ex student of mine. As I walk by I have my ass smacked and says that he has next and in a weird way I’m kind of turned on. I stop he says next time we are going to have you stay for a couple of days. I walked out embarrassed and horny as fuck. I was text and am coming over this weekend

  • My Mouth Got Me An Ass Fucking

    When I'm around people I know really well I sometimes say things I shouldn't say. We were in our weekly staff meeting and someone said, that someone got chewed out really bad in the hall. Before my brain engaged I said 'so they tore him a new asshole'.

    My boss, who I worked with since I graduated from college, shot me a look that took my breath away. After the meeting he called me to his office. He started with telling me he was very disappointed in me, that type of language was totally uncalled for, and coming out of my mouth it made me sound like a two dollar street whore.

    "Did I even know what I was talking about?"

    I had to sit in his office for an hour while he handled a telephone conference. When he was done, he told me to come around his desk, and bend over. He pulled my pants right down and stuck a finger up my ass. "Now, that's nothing, having a dick shoved up your ass, tearing you a new asshole, is nothing you want to experience". He let me pull my pants back up and went to wash his finger.

    It was close to the end of the work day, so he told me to come with him. He took me to sex store to buy lubricant. He also bought condoms, because going up my ass was a good way to get an infection. "So you are going to tear me open?"

    Back at my apartment he told me to get in the position. He used his finger to lube me, and had me pull on down a condom on him. Now, take it, and keep your mouth shut. He went in with one thrust, all the way in. "Now settle down and enjoy it". It wasn't enjoyable, it was completely different. It crossed my mind me and my boss would never be the same again. He finished and I removed the condom.

    "That's once, never do this again". The next morning he took his sweet time on me.

    I've learned my lesson, and now I'm his permanent addition. We have normal everyday sex only. He wants me under him, face to face. I am a lot more guarded around him, I don't even use the word vagina. But sometimes at night when he's behind me, and he's hard rubbing himself against me, it crosses my mind to ask him to 'take me up the ass again". But I don't say anything, I just turn myself under him and pull him on top of me.

    Sneaky Wife

    At a party wife (36) snuck off with a young guy collage age to have sex. She thought i had no idea but i saw them . I never really thought or expected her and him to actually go through with it. Of course you trust your wife to talk to any person they want to at a party. Especially if you have no idea who it is thinking she might be a potential client.

    Over forty five minutes later she sneaks back in as if nothing happened. Laughing smiling and grabbing a drink as if nothing happened to play it off. Soon he appears with same expressions. I didn’t dare to ask and she disappeared to the bathroom, another sure sign. I’m talking to guys drinking bourbon smoking cigars sneaking her way when she appears joining a group of others.

    When we get home and ready for bed I’m ready to discuss what happened and hopefully some good drunk sex when she comes out of the shower ready for bed she just rolls over and goes to bed. I’m even more hurt and furious and tell her next time you’re going to give your pussy and mouth up to someone make sure he’s a potential client and not just some random young tall guy who you want to get fucked by. She mumbles "babe I’m sorry I got carried away and things got out of hand." Oh yeah I say? "It’s funny how you are so happy when I’m away from you I can’t imagine what happens when you're out with your friends." I tell her "I’m sure you gave it to him good and he’s going to mention it to everyone while laughing. Yeah that’s how it works. He’s going to brag how you sucked his dick and swallowed his nut while he just sat and enjoyed. Not to mention how he fucked you like a cheap slut. Yeah, to you he was a great fuck but he is going to have the last laugh."

    She’s very apologetic and very upset but the more I think about her I’m sure she’s been doing this for a while. Our sexual life died a few years back and she has been enjoying my riches, nice cars, house, dinners, trips, parties, events, clothing and jewellery. She thought she had the last laugh.

    I Sat And Watched Them And Caved

    Recently went out on a girls night with a few close friends. My best friend and I rode together met everyone at this little restaurant bar in town. Our husbands mine and Gianna’s my bestie went to play cards at one of there friends house so we knew they would be there late so we where in no hurry. By 7 the place was packed and it was getting a little to crowded for me so i suggested we find another place or head home. She agreed but first I was going to use the restroom. When I came back to where we were sitting at the bar there was 3 black guys chatting up Gianna. G her nick name is a short brunette wears glasses has big tits and a curvy rear. I’m a similar build but have strawberry blonde hair and a little bigger ass. I have problems finding pants that fit or I’m comfortable with so lots of dresses lots of skirts and leggings. Tonight I was in black legging a snug top and heels. G had a drink then I had one more flirting the guys lived close to this center walking distance literally across the street and with the booze and how loud it was we ended up at there place. We should have left but didn’t we made that mistake. We got tot here place got to site down they where a few years younger very attractive. To many drinks I went to the rest room at their place and when I came out G was gone. It was me and this guy named Rick they called Ricky. We chatted he was super one on me I kept mentioning my husband kids he gave me another drink I took it to try and relax it hit me hard. I heard noises coming from the back I walked in Ricky followed as I walked he said it sounded as they where having a good time in there. I pushed the door open G is only in her thong on all 4s one from the back and one in her mouth. The size of there dicks is why I could not look away. I kind of asked what she was doing I knew what she was doing. She said nothing but grunted and didn’t even look at me. Ricky at this point was rubbing on me and had slid his hands down the back of my leggings and I willingly had opened my legs. It was the same rhythm as Gs railing. It happens so fast that I was on all 4s facing the opposite way of G. The guy was in G and would pull out and use my mouth to fuck. Ricky was behind me I turned back in time to see the largest cock I have ever had seen and experienced. The first few times it hurt then the hurt was a good pain then he found my G spot and he and the others made the comment that this slut squirts and shakes when she cumms. I did just that over the course of a few hours each one fucked us I lost count after a few orgasms. At one point my face and Gs face where in each other’s crotch’s. I had my first air tight so do G I walked in there place a good wife and mother as did G I stumbled out a well used slut promising to come back even exchanged numbers. I got home around 1 had a few texts from my husband saying he was running late. I text him ok went to Gs and hung out fella sleep and just got home. I walked in luckily the kids where at there grandparents. I looked at myself in the mirror I had dry cum on and around my neck my hair was sticky my hips and thighs where bruised. Not bad but enough to raise questions if seen. I showered and got into bed. Luckily my husband drank a bit to much he slept in. Woke up late the next day and it gave me time to take a bath and relax I had some very crusty bottoms when I woke. I leaked a lot. I was sore the next day the following day my husband wanted to have sex and I didn’t lights off could not see. I could hardly feel him he nut fast I faked it. Showered and went to watch tv when the kids showed up. G text me one afternoon and asked me to go over with them the guys from the night. I said not today good thing I saw G and there was 3 more guys there 6 total and they ran a train on her. She could hardly walk. I went back a few days later and had the same treatment but I was told that I was a better fuck then G. I had no issue when I was air tight multiple times. Each one got my ass and again I lost count and fell asleep. Woke up to my ass getting slammed I must have squirted a dozen times.

    Unwise And Uncontrolled But I Can't Help It

    Until July I was a normal suburban mom. I loved my husband, our two high school-age boys, and our life. I don't work (my husband earns more than enough) but I was never
    bored.

    My younger son's best friend Brett came over, but my son was out. I noticed how beautiful Brett's body is. Muscular but a little chubby, like most hungry teenage boys. He was wearing shorts. It was pretty clear that he is a big boy for his age.

    I don't know what came over me but I invited him in for lemonade. I patted the back of his head and voiced "Good boy!" as he came in the door. He looked at me with the neediest expression and said, "You should do that again. My mom thinks I'm a fuck-up." So I did.

    And there I was making out with a 16-year-old boy. (Don't worry, that's the age where we live, and he clearly wanted it!)

    I gave him his first and best blowjob. He lasted all of 2 minutes before shooting the biggest and sweetest load of cum I'd ever tasted.

    Thank God my husband and sons were out all afternoon. Brett gave me loads 2, 4, and 5 in my pussy. 3 was in my ass.

    Brett has always been responsible and over-protective. That first afternoon, seconds before he shot his first load of babymakers into a pussy, he apologized. "Mrs. Smith, I know from health class that this might make you pregnant, but it feels too good to stop." I cried out from what must have been my fifth orgasm, though honestly, I'd given up counting.

    What I cannot explain is that I am in love with him. Serious, leave your husband and kids love. Brett feels the same way about me. He gets really jealous and asks if my husband fucked me. Thankfully he rarely does, these days.

    With back-to-school I was nervous that Brett would date other grils, but he was so sweet and reassuring. He only likes older ladies.

    It was a bit awkward when I asked my son if Brett was dating anyone. Thankfully not.

    Now I can't sleep unless I see Brett. I'll go out for a walk and he'll pick me up in his dad's Jeep and drive me down country roads where we can fuck. Our child was conceived in that car!

    Yes, I am carrying Brett's baby! The plan is for me to pass it off as my husband's until Brett graduates from high school and we can run off together.

    I know I will be giving up everything and everyone from my past life, but the feeling I get from being Brett's lover is so powerful.

    Sometimes I am his lover, sometimes I am like his supportive and encouraging mom. He is a man, but still a boy, when he gets mad about my husband. "Mrs. Smith, he doesn't deserve you."

    How come a teenaged boy truly sees me, when my husband doesn't of 24 years doesn't notice me.

    Brett, I love you, I love our child, and I live for the day when we can escape together.

  • I'm Now A Queer, A Sissy And Nothing Can Change That

    My first cock happened when I was on the track team. Part of our workout was to run several miles, and I chose to run around the city park because of the scenery. I ran in the mornings before school, but that day was Sunday and I ran late in the afternoon after Sunday dinner. Along the way I came across a man with a car that was stalled so I stopped and asked what was the matter. He told me that he had no idea really, but he also didn't have any money. To confess completely, other than the ignition I have no idea on how to start a car.

    We talked for a few minutes, I explained that the nearest garage was a few miles away, as most gas stations don't have full car service. He was upset about it and felt like life had turned a bad page against him. I told him I lived a few blocks away and to come with me, and from the air conditioned living room he could think of his options.

    My parents went back and forth about getting him a motel room or letting his stay with us. At the end, he stayed the night, and he had to deal with his car the next day. It was well after midnight when I was awakened by him touching my shoulder. He told me that he wanted to get in bed with me and cuddle. He got in behind me and pulled me up to him in a spoon arrangement. All I had on was a pair of briefs and he was hard as nails. He humped against me and he got bigger and harder. He whispered that he knew I was going to like it and he pushed my briefs out the way and started to poke and push against me, until he got it in and then started the process of getting in deeper and deeper. I turned onto my stomach and on my back he worked himself in until he could go no further, then started to fuck in and out until he came inside of me.

    He stayed with me until close to five before sneaking back to the guest room. I lay there, alone, with a wet butthole. I wasn't a man anymore, I was a queer, a sissy. My father agreed to pay for his car to be towed to a garage. He had a small problem with his fuel pump, which was fixed for a little over two hundred. With his car back in order he called and left me a message. He would be parked where we first met and for me to come over after I got home from school.

    He told me it was time for me show respect and suck him. If I didn't suck him he would fuck me. I sucked him in his car and he kept my head down with his hand until he managed to unload in my mouth. He told me I was a cute boy, and he wanted to kiss me. Not to ever say no to him, and he kissed me before letting me know that he had my number and when he was around again, he would call me.

    I can't say I have gotten over him, or that I have dated a girl since that experience. I have college to go this fall and I'm scared I will be a college sissy. I know what it means to have let a man fuck you, any hope of being a man is no longer something I can look forward to. I called him to let him know where I was going to college, in case he comes around that way, he can call me to go see him.