Painkillr

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Gender: Straight Male
Age: 55
Relationship Status : Not specified
Profile Visits : 331
Number of Comments : 46
Number of Confessions : 0

Painkillr's Favorite Confessions:

One day I was down at the beach in a pair of speedos and who do I see but my bosses wife. I hoped she wouldn't see me because even though the speedos covered me they were still rather revealing. Anyways his wife saw me and came over to chat. She seemed to be pleasantly surprised by what I was wearing. I just decided to accept the fact she had now seen me wearing very little. Her eyes did have a tendency to remain on the bulge in my speedos. It was pretty well a casual conversation until she brought up how the speedos seemed to leave little to the imagination. She mentioned they were very snug on me and without any warning she put a finger into my waistband and pulled out. She was now looking into my speedos at my cock and didn't say anything. I was in shock and didn't know what I should do so I just froze. When I finally came out of my shock I realized it was too late to do anything, and being it was my bosses wife, I didn't do anything. Finally she took her finger out and looked around. She told me I didn't seem shy and told me to quickly take them off before someone showed up. I was in shock again by her request and when she repeated herself and I did nothing she took it upon herself to pull my speedos down to my ankles. This time I was fully exposed and she was looking me all over. I must have been that way for a few minutes before told me someone was coming and to pull them up. Before she left she told me if her husband finds out I had just exposed myself to her like I did he would fire me. I told her she was the one who got me naked. She asked who he would believe and she put a big fake smile on her face as she left.

I was working late one night doing a server upgrade which was going to take hours. My boss was out of town so when his wife showed up I was a little surprised. She had only come in to pick up some mail. We talked for a bit and when I mentioned y back was stiff she offered to give me a back rub. I didn't know how appropriate that would be but she pushed the issue being that it was about 9:00pm at night with no one around I gave in. She took me to her husband's office which had a couch in it. She had me take my shirt off and lay face down on the couch. She began massaging my back and it felt pretty good. She said she had to get to my lower back and ask for me to pull my pants down to get to it as they were in the way. I had to unbutton and unzip them to be able to do that. I figured she only needed them down a few inches so that is as far as I pulled them down. She said they needed to come down further and took it upon herself to just take them right off me. She then takes my socks off which I thought was a little strange given that she was only massaging my back.

I was now just in my underwear with my bosses wife, who was about 20 years older than me, massaging me. She asked how the massage felt and I answered truthful which was that it felt great. She then says she will give me a full body massage and without warning pulls my underwear off. I am now naked in front of my bosses wife. Her massage felt more than just great and I could feel hands brush against my balls when she went between my legs. I was worried if she was going to ask me to roll over on my back and when she asked me to I did it with no hesitation. I was fully exposed to her with my cock very erect. She noticed and mentioned she could see I was enjoying the massage. She massaged my whole front but avoided my cock and balls which I figured she might do. We were pretty done when she began to work on my cock. She was stroking it and asking me how I liked it. I told her I liked it very much. She was teasing me and was very good at it. I was close to cumming and she knew when to slow down to prevent it. This went on for a while before she finally did it. She had her hand wrapped tight around my cock stroking and I blew like I never had before.

She helped clean me up and we talked for a while. I didn't even bother getting dressed until she said she needed to leave. The next time she saw me there was no mention of anything that happened and for awhile never was. One time I asked her about it. She told me I was a little too old for her liking but wanted to at least get a look at my body for her own curiosity.

Swim At Bosses Condominium

I was at my boss's condominium helping him with some work. His condo has a swimming pool and he suggested we take a break and go for a swim. I didn't have a swimsuit with me and his wife told me they have some spares that I could borrow. She handed me a pair that fit relatively well but I was a little concerned they might be a little loose. It was only me and her there when she took it upon herself to check. She put her finger in the waistband of the swimsuit and pulled it out to see how loose it was. First it was the side of the swimsuit she quickly pulled out and then the front. The front she pullout longer and she was taking a good look down into it. She then went behind me and put 2 fingers, about 8 inches apart, and pulled out and somewhat down. She took a longer than usual look at my ass which she was exposing. She then went back to my front and put 2 fingers in the waistband like she had with my backside. She pulled out and down and my cock was fully exposed to her. She starred at it and and then looked me in the eyes before she pulled them right down to my ankles. She told me I looked nice and to pull them up. She told me it best that we just keep this between us as her husband wouldn't like me exposing myself to her like this. I told her it was her that pulled my swimsuit down. She asked who I thought he would believe and she smiled.

My boss finally joined us and only me and him we went for a swim and nothing was said about what she did. We walked down to the pool in just our swimsuits as he said the pool supplies towels .

We came back from the swim and right away his wife asked if those were wet referring to our swimsuits. He said yes and took his off. He told me to hand her mine too but told me to turn my back to her first so she doesn't see what she shouldn't. He said she would get me a towel and that he was going for a shower and then left me naked with his wife. It was like deja-vu all over again. The towel she was supposed to get me didn't arrive before she had some fun with me first. She took me to the kitchen, had me stand in front of the sink facing it, told me to start stroking and that I can make a mess into the sink. I refused. She told me it was only going to be between me and her. I refused again. She said my job depended on it. I gave in and did what she asked. She intently watched as I stroked my cock and shot my load into the sink. It was cleaned up before her husband got out of the shower and in just the nick of time.

He found us in the kitchen together. I was using my hands to cover my junk and he asked why I didn't have a towel yet. She said I asked about having a shower and we were waiting for him to finish. He laughed. Said I must be pretty stressed out and embarrassed being this way in front of his wife. His wife made a comment that I accidentally flashed myself to her a few times. He laughed and said she must have loved that. He told me not to worry as things happen and we were all adults. He then tells me since she already saw a few flashes why bother covering up. He says "Come on" and then orders me to remove my hands. He that says "Didn't you hear me? Remove your hands." He didn't know what happened earlier but now I was naked in front of his wife again. He told me to go have my shower now which I did.

I showered and both him and his wife came in as I did. They talked to me as I showered and soaped myself up. It was embarrassing as it was a shower stall with clear glass walls and doors. They could see everything I was doing. His wife must have been loving this as she got a cum show earlier and now she was getting a shower show.

I finished, got dressed and left. His wife always teased me about that day and what she had me do and what she saw.

Gym Workout

I don't know what to think of this. At work we have a fitness room setup with weights, exercise bikes, treadmills, etc. I was after work hours and I was the only one working out out. The bosses wife comes in and asks me if I had seen her husband. I told her I saw him about an hour ago and that was all I knew. I was in a t-shirt and shorts and didn't expect what she did next. She put her fingers in the waistband of my shorts and pull out and slightly down . She was looking down at my cock which she just exposed. She then let the waist band go which covered me up again and told me to turn around. I did as she asked and once again her fingers ended up in my waistband but this time she pulled my shorts right down to my ankles. She told me I had a nice ass. I didn't know to reply so all I said was "Thanks". She moved to the front of me and grabbed my cock. I began to stiffen up and she told me her husband would not like me getting aroused by her. She told me to keep this between just us or I would be out of a job. She left and I finished my workout.

I jumped into the shower and she happened to show up again. I froze and she told me to continue showering. I showered as she watched which was a little intimidating but a little arousing at the same time. I finished and toweled off. Before she left she said her husband wouldn't like her seeing me this way so we would just keep this between us.

Why Did I

I’ll make this short and sweet. I have always hated my brother’s friend Robert. An arrogant asshole who talks like women are one step up from a gym sock. We all grew up together from grade 6 on so I know him well.
He’s a plumber by trade and I was in a real bind over a bad water heater so my brother sent him over. When he finished I assumed there would be no charge. He said it would be $200 or I could blow him. I said, well that’s not going to happen and brought him the $200 and a cold beer. I poured myself a glass of wine and then accidentally knocked it over breaking on the floor. As I was wiping it up when he took his cock out of his pants, average at best, and stuck it in my face. For whatever reason I started sucking on it with him placing his hands behind my head and thrusting his cock down my throat. He didn’t give a damn that I was chocking or having trouble catching my breath, he just kept ramming it into my face. When he came he held my head down hard with me gagging and his cum shooting down my throat and out of my nose. This part really bothered me. He then gave me back my money and said he’s had better and then left. You would think I would be really angry with myself and him but instead I wanted him yet I’m not attracted to him. Well that was two weeks ago. Last night he knocked on my door and said he was going to give me another chance. ANOTHER CHANCE??!! I again I sucked him off with him then tearing off my sweat pants and fucking me hard. Like before, he put on his pants and left. What is wrong with me?

MY TEACHER

When I was in Junior High (eighth grade), I had a cute young teacher named Miss Almond. She was petite, with round breasts and a nice round ass, always wearing a skirt and blouse. When she walked, I noticed that her ass would twitch. She had a habit of walking around the classroom behind us as we all faced the front of the room while she asked us questions to answer. I sat in the back row. One time, she asked a question and when I put up my hand to answer, I accidently touched her breast. I apologized and she smiled. No one in the class noticed.

After that, I kept thinking about her. Whenever she caught me looking at her, she would smile, close her eyes, nod her head slightly and then look back at me. I volunteered to help her out after school. Over several weeks, we got comfortable and friendly with each other. Quite often, she would touch my arm or leg. I knew that meant something was on her mind, but I didn't have the nerve to try to find out.

One winter day, I had been at school late helping her. As I left to walk home, Miss Almond offered me a ride in her car. As we drove, she put her hand on my thigh. I got excited, but, again, I didn't have the nerve to do anything.

She asked if I didn't mind talking a bit before she brought me home - I told her my parents were still at work, so there was no rush. We drove around, talking about various things. She pulled into a large parking lot serving a row of stores, where we sat with the heat on. After some small talk, she asked if I had a girlfriend-I told her that I didn't have one yet. She told me that she had had just one boyfriend in her life, that she was 20 years old and that she was lonely.

Then she mentioned the time I touched her breast. My heart started beating faster when she told me that she had been thinking about it. She asked if I had been thinking about it as well. My throat went dry and I gulped as I told her YES. With that, she looked deep into my eyes as she took my hand and held it on her breast. She leaned over to me and put her mouth on mine. As her tongue entered my mouth, my cock was instantly erect. I reciprocated, kissing her back, tasting her tongue. Her lips were full and soft and her tongue was like a snake! She slid my hand into her blouse so I could hold her breast. For what seemed like an eternity, we kissed slowly and passionately, with my hand cupping her breast and her hand on my crotch. When we stopped for a moment to catch our breath, she told me "You can't tell anyone about this, okay?" Of course, I agreed.

She unzipped my pants and slid her hand around my cock, holding it. She took my hand off her breast and placed it under her skirt between her legs on her warm pussy. We continued making out, but went no further than kissing and fondling each other.

The next day at school, we acted normally. A few days later, she asked me to help her carry some large items to her car. She told me that she needed help bringing them into her apartment, so we drove there. Once done, she asked me to stay for a while. When she emerged from her bedroom, she was wearing just an over-sized tee-shirt.

We made out on her couch. This time, I was a bit bolder, gently stroking her pussy. She too was bolder, pulling my pants off, with my hardon popping out. She told me I had a nice cock. Gripping it, she gave me a heavenly blow job, stopping before I came. Then she laid back and opened her legs. Her dark hairy pussy was beautiful. She asked if it was my first time. I lied and told her YES. (A year earlier, I had been initiated by my 18 year old "baby sitter" who showed me how to eat her pussy and fuck a woman properly.) She asked if I knew what to do. I asked her to show me.

She pointed to her pussy and showed me where she wanted me to lick her. At first, I acted like I was new at it, but soon I was licking away like a pro, with my hands on her inner thighs. She moaned and pulled my hair as her legs shook. As I licked and sucked, I knew when to stop for a second or two as a tease and then go again-each time I did this, she came again and again. Finally, she told me she had to take a break. We made out some more as she stroked my cock.

She asked me "Are you sure this is your first time?" I assured her that it was. With that, he pulled off her tee-shirt and sat on my lap. She moved back and forth until she guided my cock into her wet pussy. She told me not worry as she was on "the pill." She went slow at first and then faster and faster until I exploded deep inside her, gripping her ass cheeks. For a long time, we just held each other, tongue kissing, with my still erect cock inside of her.

We got together every few days or weeks after this, whenever she wanted to. As young as I was, I realized that she didn't want a love affair or a relationship, especially with a student of hers. I just enjoyed making love with her. After the school term ended, Miss Almond transferred to a school in another city with better pay and benefits.

FRIEND'S MOM

When I was 20, my friend's gorgeous mom would flirt with me, "accidentally" sometimes revealing parts of her naked body to me. Sleepovers at his house were rough for me - all I could think of was his hot mom.

One night, as everyone was asleep, she came into the living room, wearing a very short nightie. I was laying on the couch. As she put a blanket on me, I stroked her leg all the way up to her pussy. She let me feel her up for a while and then pulled out my cock and sucked me off. With her finger on my lips, she straddled me, fucking my cock at her pace. Her juices dripped all over my groin and legs. She finished by sucking me until I came in her mouth.

After that, I was hooked.

-Free Lover 2021 at aol

Sis Lending A Hand

When I was sixteen I was heavily involved in competitive cycling. On one training day I was cut off by a car, went over my handle bars breaking both arms at the wrist requiring casts and operations on one arm. Wearing casts on both wrists and arms creates problems for simple tasks. They were virtually impossible, one of which was wiping myself after a movement and bathing. I needed assistance on both. My father and brother were out of the question which left it up to my mother. It was very embarrassing. I remember the first bath, after soaking she came into the bathroom, had me stand as she sponged me down. I became erect immediately with her commenting on how well endowed I am as she washed around my dithery bits. “You’ll make some girl very happy” was what she said. My brother who is four years older had told too many as to my g*ft or curse, my mother being one, this being the first time she had seen it since I was little. After a week or so my mother and father went away for the weekend leaving me with my brother who is hardly ever around and eighteen year old sister. By this time my dad rigged a device, a bent metal stick that allowed me to wipe myself but it didn’t do a great job. My sister offered her services with the bathing. I told her that wasn’t necessary, that I would soak and leave it at that. She said nonsense and insisted. I told her it was too embarrassing but she insisted. Well I let her know after soaking for twenty minutes that I was ready. She came in wrapped in only a towel which she quickly discarded, dropping it to the floor. “It’s only fair” was a what she said. “If you’re naked, I’ll be naked.” My sister at eighteen had an incredible body. I was immediately erect but unlike with my mother I did not stand. She bathed me while I laid in the water but insisted I stand so as to make it easier. With must protest I stood. She as with my mother was very impressed it my endowment saying it was the thickest she had ever seen. She then started pumping my dick, “Does this feel good?” she asked. Of course it did. She turned me to face her dropping to her knees and started sucking me off, I in the tub and her on the floor. I couldn’t believe what was happening, knew it was wrong but I wasn’t about to stop her. She commented on how much pre-cum was coming out saying, “get out of the tub so I can dry you off.” Well after drying me off she took me across the hall to her bedroom laid me on my back on her bed and sat her pussy immediately down on my erection. I tried to stop her but she said she was on the pill and she wanted my, as she put it, “ fat cock in her.” Who was I to argue. Looking at her beautiful self, her wonderful breasts and body rocking my world had me cumming in but 3-4 minutes. She said, “Oh wow … that wasn’t fair!” She then moved herself up and straddled my face lowering her pussy onto my waiting mouth. She instructed me on how to suck and lick her clit. That was all good but I dropped a lot of cum in her which was now flowing out of her pussy into my mouth and on my face. I did not like it a bit but pushed ahead following her instructions. I can remember as if it were yesterday her hands on the wall and watching her big tits over my face quaking with my work on her clitoris and the glorious look of ecstasy on her face when she suddenly came. All this made me rock hard again and she quickly took hold of my cock slipped her pussy back down on it riding it hard hammering us both back to a mutual orgasm. We laid there together for over an hour talking with her playing with my balls, bringing her tits to my face so I could suck on them and stuff like that. We never made mention about any of this to anyone. We hooked up from time to time when ever we were horny. She blew me whenever I asked once while I watched football and I ate her out on command whenever she wished. Of course all that stopped in our 20’s until we both found ourselves divorce and reminiscing about those days many years later. Neither of us were as attractive in our forties as we were back then but we actually lived together pretty much like husband and wife for four years splitting up once she met a great guy. Unfortunately in the last three years I lost her and our parents. They’re all missed and her Bo and I are great friends. I feel comfortable on here since no names are mentioned but other than this and admitted suspicion by others, all will go to my grave.

Seeking Advice For A B'day Present For My Hubby

I ma looking for some advice, especially from women.

My name is Marsha, I'm 45, married to Ed who is turning 50 next month.

I'm thinking of giving him a birthday present I'm quite sure he would love. It involves him, me, and my best friend Debbie.

A few years ago Debbie and i became lovers by accident. We were going to concerts together, sometimes one night and sometimes 2 or 3 depending how close to home. One night after the concert we were wide awake when we got back to the hotel. I took a shower and got in my bed, then Debbie showered. We started talking about the concert and many of the hot guys we saw there. Debbie asked me how often Ed & I have sex. I said it depends, but at least 2x. She confessed that she hasn't been fucked for almost 2 months. She broke up with the guy she was seeing. I was consoling her and before I knew it she kissed me. I jumped back and she apologized. I said no apology needed and kissed her. We had incredible sex that night. We both said we didn't know each other were into women. I told I've never been with a woman. After that we fucked often while home and every night when we went away. I never told Ed.

Here's the advice I need.

I talked to Debbie and asked her if she would be interested and willing to have sex with Ed for his birthday. It would be the three of us. I know Ed would be ecstatic. While discussing it with her many questions came up. 1) would i be jealous 2) would it be one and done 3) how would we set it up

I'm sure there are more. Right now I can say I won't be jealous, but considering it's never happened I can't be sure.

If you've been in this situation your advice would be greatly appreciated.

Thank you in advance
Marsha

NEIGHBOR AND HER SISTER

A post here about a guy whose female cousin brought over her younger friend to have sex with him reminded me of something I experienced.

When I was in my late teens, I lived with my parents in a heavily Puerto Rican neighborhood in NYC. Home alone after school each day, I'd walk around my apt naked. The apt had a back door exiting onto a rear patio shared by other apts in that complex.

One day, I noticed several PR girls looking into my living room window from the patio. I pretended not to notice them, so I sat on the couch and jerked off in front of them. I did this on several occasions.

Not long after, as I was naked again, I saw just one girl watching me through the window. After a while, I quickly opened the patio door and confronted her. She didn't run away. She just stared at my cock. I motioned for her to come inside my apt and she did. I took her by the hand and brought her to my bedroom, where I laid her on my bed, pulled up her dress, pulled off her panties and ate her pussy before pushing my cock into her. We never said a word the entire time. We didn't need to.

After that, she would be at my door almost the same time every afternoon. She would go into my bedroom, undress (she wore no bra to cover her beautiful little brown titties) we would have great sex and she would leave.

One day, she came to my apt by way of the patio door with her younger sister. They both went right to my bedroom. Holding my cock, she told her sister something in Spanish. She sucked my cock in front of her sister and then guided it into her sister's mouth. She then got undressed and had her sister do the same. They both laid on my bed. I ate her pussy as her sister watched. Then she opened her sister's legs and motioned for me to eat her sister's pussy, so I did. As I did, she massaged her sister's pussy, leading her to orgasm. I fucked her in front of her younger sister, who was fascinated by what she saw, especially when I came all over her older sister's belly. After I rested for a few minutes, she had me fuck her sister as well.

This went on with both of them for months, until the older sister got a boyfriend. Every time we saw each other on the street after that, she gave me a knowing smile.