The first date I had with my eventual wife was a nice dinner out and a fair amount to drink at a club down the street from the restaurant. By the time we left M was giving me plenty of positive signs and keeping her body pressed close to mine. It had been a while for me and I felt some tingles. It felt great to have such a sexy woman hanging onto me in public and hoped I would run into someone I knew. When we pulled into her driveway to drop her off and she invited me in I was surprised and happy beyond words. I guess she had had plenty to drink and it wasn’t long before we were on the couch kissing and exploring each other’s mouths with our tongues and I was making my way under her top to her C cup boobs. I remember wondering if she was drunk because she seemed so uninhibited and actually a little aggressive. At one point she stood up and pulled her top off over her head and reached behind herself to release her beautiful tits from the sheer bra she had on. I was in heaven and realized I had scored out of my league. Between her wet deep kisses and soft provocative comments about how wet her pussy was I didn’t waste any time to get my hands up under her skirt and into her panties.
She wasn’t lying about her pussy. She was sloppy wet and within a few minutes I had her moaning loudly with three fingers buried to my knuckles. She was definitely wilder than any of my previous experiences and my mind flashed about my long term interest in a woman who was acting this easy with me on a first date. The way she was bucking up against me on the couch didn’t leave me much time to dwell on such mundane matters and the sounds she was making and the dirty words of encouragement kept me focused on her seriously juicy pussy. I remember that my hand was completely coated with her slippery juices and was literally dripping onto the couch.
At one point as I was probing and rubbing on her pussy and clit I ran my fingers across her ass hole. Her response was obvious and even though I had never done it to any woman before I began circling my index finger around her hole, spreading her slippery juice around it and gently pressing onto her puckered hole. There was no question she was responding wildly and I decided to slip a finger into her ass.
To say she seemed to like it would be an understatement. She literally pushed her ass against my finger and was telling to “fuck my ass baby”. I soon had three fingers deep in her ass hole and wasn’t really being gentle. It wasn’t long before I was doing more than just thrusting my fingers into her, I was literally pulling and stretching her hole to the sides in response to her vocal and physical responses. I couldn’t believe how she was responding to what I was doing to her ass. I felt like I had to be hurting her but she kept talking dirtier. In disbelief and after I was pretty sure she had orgasmed twice I slowed it down despite her undoing my pants and obviously ready for sex. With her grabbing the crotch of my pants fairly hard I did my best to pretend I was a gentleman and didn’t fuck on the first date. It must have seemed pretty weak for sure. As she sat up covering her boobs with her hands I saw her beautiful sexy pout as she told me “your no fun”.
Well after a first date like that I wasn’t sure what to think. She was definitely beautiful and she was definitely wild. I thought about how sexually experienced she must have been. I wondered if it was just because she liked me but quickly dismissed her obvious sexual uninhibitedness as much more than that. I considered how I would or could imagine myself in a relationship with a woman clearly much easier than the more typical women I had had relationships with before. I felt insecure and imagined how jealous I would be of her. But she was so damn beautiful. I kept thinking about all the sexy ways she had about her, her looks, how she dressed and the soft provocative things she said and abandoned trying to figure it out and just called her and asked her over to my place for drinks.
I’ll skip how sexy she dressed up for our date, how confident she looked and how completely unapologetic she was about our first date. I was amazed how casual she was about leading me into the bedroom and directing me under her short dress and between her legs “to finish what I had started the other night”. It was only a minute before my face was slathered wet with her wonderfully juicy pussy and only a few more minutes before she was pulling me up towards her to mount her. I guess I was scared and intimidated and self conscious in the arms of this beautiful confident (read powerful) woman and I felt small.
With her legs wide apart I realized there was no time for hesitation and I reached down and slipped myself into her and pushed in hard to get going. As I slowly and deeply thrust myself into her I simultaneously felt small inside her and felt her energy begin to fade. I tried to keep my penis stimulated with a rhythmic stroke but her sloppy pussy felt like I was barely touching the sides. When I looked at her she was smiling and looked somewhat amused and began encouraging me with repeated and seemingly overly dramatic “come on baby, fuck me”, “ fuck my horny pussy baby” while digging her fingernails into my sides and ass cheeks. Her body’s response was nothing like I had seen on our first date.
To be honest I was really struggling and looked down at her tits and beautiful erect nipples just to maintain my hardness. Her skin was so smooth and tanned as I realized I was between the luscious legs of a goddess.
She kept talking dirty to me but it almost sounded like she was mocking me. “You feel so good baby, fuck me harder” just didn’t seem honest and I was feeling so little contact inside her that I realized I was failing. I was struggling but I kept trying, thrusting myself as hard as I could, trying to push deep but I could barely feel any contact inside her and my penis felt cold. At some point I realized she was just laying there, with her legs spread wide and not moving while I embarrassed myself. After probably 5 minutes I just stopped. As I felt my limp penis slip out of her I heard myself apologize and i just slipped down between her thighs and began mouthing and licking on her until she had a back arching, quivering orgasm.
It was a week before I called her again and was surprised she was as friendly as she was and accepted a dinner invitation at a nice restaurant in town. She dressed up and looked gorgeous and I was happy to have such a beauty on my arm as we walked the downtown sidewalks. After the nice catch up talk there were a few minutes of awkward avoidance of our last time together which ended with “you were just nervous” followed by her usual playful, flirtatious banter.
My confession is that after that first pathetic attempt to have sex with M, I only had my penis inside her six or seven more times in the nine months we dated and the five years we were married combined. She had had a friend with benefits that she never stopped sleeping with as we started dating. It came out after about three months when she told me that I obviously wasn’t interested in her sexually and she gave me the “I’m in the prime of my life” routine and then topped it off acting surprised and angry that I could be so dense that I didn’t know. Apparently they had been getting together at least once a week for three years.
We continued to date and have nice dinners out. I bought her a few nice dresses, some cute outfits (she said I had great taste) and shoes, expensive lingerie, some jewelry (she looked sexy as hell in chokers), perfume, spa treatments etc etc. We had some fun weekend getaways together. We always slept together and cuddled and fondled and kissed and we had two or three more attempts at intercourse which ended like our first, in a very unsatisfying and humiliating experience. Our “sex life” while we were dating settled in to me performing oral on her as often as I could. She seemed to enjoy it and always orgasmed and I couldn’t get enough of her taste and how wet she got and the incredible feelings of submission that I had with her.
M had an very active sex life the entire time we were together. There were at least thirty two men that I am aware of, most of whom I helped her to meet in the 5 1/2 years we were together. Many were one nighters and weekend flings but we met several “perfect” men that became friends who we traveled and partied with for months and a couple even several years. There were 3 women she had relationships with that I don’t really count and one couple that I did. Keeping her pussy “happy” by helping her spend time with other men became a part of my relationship with her to make up for my “failure of marital duties” as she called it. In addition to the men I met or saw her with I know there were also a two men she met on different business trips that for whatever reason she was reluctant to tell me about, a couple (3 or 4) younger guys she was with on a weeklong houseboat trip with the girls and at least two men that she said I knew but refused to tell me anything more about.
Looking back I cannot feel more pathetic as a man and at the same time grateful. M was the perfect woman for me and our cuckold relationship was the experience I think I needed and wanted all my life. Probably the experience I was meant to have. Thank you for reading this confession. You are the first to hear the truth.
If there is any interest, I will confess to what it took for me to keep a beautiful 38 year old like her around for as long as I did in a separate post.
Never shared with another soul but feeling safe here on my fap page. Thanks for being part of my therapy! Comments welcomed.
This happened when I was 16, a sophomore in high school and had been going steady with a gal for more than a year and a half. She was not my first lover but definitely my first love. It was good to have a steady girlfriend and to be having regular sex at that age. She was the epitome of a SoCal beach girl, cute, blue eyes, sandy blonde hair, fit slim body, perky C cup tits and a year round tan. We ditched a lot of school, spent a lot of time at the beach and in the local mountains and partied a lot together.
All was good until the day a few of us friends were hanging out at her house, waiting for her to get home and a mutual friend came out of her bedroom and showed me a page of what looked like a diary. It was a full-page list that had dates, names and places. My heart raced as I saw the names of some of my classmates and more painfully a couple of the school jocks and several names I recognized who were seniors. A few of the entries didn’t have names but had descriptions like landscaper, gas station guy, liquor store guy etc. There were some graphic notes and stuff in the margins that made it obvious this was a list of her sex exploits. When my brain stopped spinning and I was able to take a breath I realized almost all of the dates were in the months we had been together. There were over 20 entries. I was absolutely stunned and sat there in complete disbelief. I literally did not believe what I was looking at and told my friend to put it back.
I remember struggling emotionally for weeks with what I had seen but my denial allowed me to continue our relationship for several more months without ever saying a word to her. I was heartbroken and seriously conflicted, not wanting to loose her but not able to come to terms with what I tried to deny I saw. I felt jealousy for the first time. Not fun. For the first time I was watching how she dressed, specifically when we weren’t going out together and how often she went out braless. I was anxious when we weren’t together and felt suspicious when we were.
I remember beginning to imagine differences in her body when we made love and wondered if she had added a name to her list. I noticed she seemed more distant and I started having performance issues with her in bed. I couldn’t help but compare myself to the names that were on her list. She seemed indifferent at times and I couldn’t stay hard long enough to cum. Her comments to me about these issues became less loving and that only made it worse. Other times she seemed her usual horny wild self and I came too quickly because I couldn’t help but imaging her acting this way with other guys.
I finally got so torn up with how things were that i brought it up and she totally denied everything. She looked me in the eye and told me how much she loved me and that she would never do that. I was young and in love and wanted to believe her. Looking back I was just plain stupid. I also realize that she may have been a real nymphomaniac. Most importantly, she gave me my first taste of the powerful excitement of being humiliated by a beautiful woman. It was my first experience of being cuckolded, although involuntary on my part, many many years before I would even know what that word meant.
Word went around of a big house party coming up on the edge of town in a few weeks. One of those bashes with a rock band and kegs that sounded fun until somehow I heard that she had already been invited, by somebody else. When I asked her about it she nonchalantly admitted that she had been and that I should come along. She seemed a bit awkward and I was seriously jealous thinking about who might have invited her but I didn’t say anything more. Part of me wanted to know.
When I picked her up that night, she looked cute as ever and wasn’t hard to notice her braless tits showing off through the cropped top she had worn under her black jacket. There was already a pretty good crowd when we arrived and we had to park quite a ways up the road. I remember walking with her toward the house and how weird she was acting. The moment we got to the front of the house she refused to stand close to me and literally wiggled away from me when I tried to put my arm around her. She kept looking past me and around like she was looking for someone and every time I tried to get face to face with her she scooted a couple feet away.
As dumb as I may have been I finally realized she didn’t want to be seen with me and I felt like she had set me up. It was pretty obvious she was meeting someone else. I was so hurt and frustrated and angry that I went into the house to find a couple of beers for us and was quickly swallowed up in the crowd. I could see the band setting up outside on the far side of the pool and was impressed with the vibe of the place. This was definitely not a high school party and there were probably a hundred people jammed into the back patio and the yard already. It was crowded but I managed to find my way to the keg, grabbed a couple tall cups and was heading back to where I left her. I was so distracted with the scene and all the good looking people I remember actually being surprised that she was no where to be found.
It would have been obvious to anyone else but I was young and in love I guess. My gut told me things had changed and I felt my heart sinking. I guzzled both of the beers before heading back toward the beer line while still looking around for her. I wanted to see who she was with and imagined all sorts of heart wrenching scenes every time I saw a blonde in the crowd. I was pissed she couldn’t have been honest with me and my mood spiraled.
The band came on loud and the whole yard seemed to bounce and all I could do was notice all the hot women and the cool looking guys hanging onto them. I wandered around feeling down and lost and had plenty to drink as well as a few big hits off the pot that was going around. I found something to lean against and watched the band for a while. I had given up on finding her or hoping for any sort of a happy ending but I remember feeling motivated in a weird way, wanting to see her with someone else. I was angry but I was also turned on at the thought of it. I guess that’s what you call masochistic. Seeing so many other hot women flaunting around made it worse because my girlfriend was a head turner and there were plenty of men around. My imagination had a field day.
The party raged for a couple hours until sometime after midnight when the band shut down. I hung around for a while and looked around for her a bit more. I walked into the house and looked around and could tell a lot of people had already left. I was thinking about heading home and I walked through the kitchen looking for a bathroom to take a leak. I went down a hallway and just as I stuck my head in an open bedroom door I see a guy coming out of an inner door doing up his belt.
The twisted thought crossed my mind that my girlfriend was probably in the bathroom and that this guy had just finished fucking her. I was buzzed for sure. As I stumbled into the room, I almost bumped into him. I walked around the bed and into the bathroom. I closed the door and took a long leak thinking about how dishonest and downright cruel to me she had been. I realized that she was probably with some guy getting fucked at this very moment.
I walked out of the bathroom ready to head home and was surprised to see the guy who had just walked out of the bathroom was now laying on the bed. At first I figured he was just passed out but I could see he was rubbing the front of his jeans and for some reason I stoped and looked. The bedroom door was closed and I couldn’t believe what I thought I was seeing. There weren’t any lights on but it definitely looked like he was working hard on a visible boner. I couldn’t look away and I remember how startled I was when he casually he mumbled "sorry, fuckin horny". He looked like a hip college guy and I wondered how he didn't have girls all over him. I remember how uncomfortably horny he looked as he continued to press down hard on himself.
Probably because of how buzzed I was and the overwhelming rejection that I was feeling that night, maybe some anger, I just stood there and kept watching him rub the front of his jeans. It seemed like a long time and I remembering being so nervous but turned on to see such a horny guy right in front of me. My girlfriend came to mind and I imagined this hunky guy would be someone she would eagerly be fucking if she were there. Finally, I heard him say "fuck it" and I watched him undo his belt and unzip his pants. The only light was coming from the bathroom but when I saw him wrestle his hard cock out of his pants, my heart stopped and without thinking, I walked around the foot of the bed, fumbled with the bedroom door lock until I was sure it was locked.
I stood next to the door and waited for a few seconds to make sure he wasn’t going to go ballistic. Very slowly and carefully I walked around and stood at the side of the bed for a moment more before slowly getting up on the bed next to him. I was still half expecting he would punch me and I tried not to flinch every time he shifted on the bed. I was completely mesmerized watching the way he worked himself. My eyes adjusted to the dim room and I could see well enough to see that he was stroking a man sized cock. This was pre internet porn and I had never seen a guy masturbate and never seen a cock as big as his was.
When I was convinced he wasn’t a fag basher I reached over slowly put my hand next to his and tried to stroke along with him. It was an incredible relief when his hand moved away and left me to stroke my first cock, the fear of getting punched vanished and I felt like I was out of my body. My head was at the level of his hips and I remember feeling vulnerable. I couldn’t get over the feeling of such a strong thick cock in my hand. His dick was completely different than what I had between my legs. Longer yes but I was much more impressed with how heavy and muscular he felt and the size of his full balls moving around in his loose scrotum. His strong muscular cock matched what I could see of his toned body.
He was definitely horny and seeing how he was responding to the way I stroked and fondled him was a rush. I could tell he was pretty buzzed and at first I felt physically vulnerable because of the way he was moving around on the bed and the way he occasionally thrusted his crotch against my hands. He was a bigger guy and to feel the strength of his entire body when he flexed was startling at first.
I realized this probably wasn't his first time with another guy the way he had been so casual showing off his cock and now, the way he was physically responding to me and the way he was talking to me. I remember looking at how impressive he looked in the light coming from the bathroom and at some point I just leaned over across his thigh and slowly put the head of his cock in my mouth. He definitely liked it and began pushing himself toward me.
It wasn’t long before my jaw just started to ache and I realized I wouldn’t be able to keep up with his thrusts for much longer. He scolded me a couple of times because I had trouble keeping my teeth off of him. Eventually he reached down and shoved my face away and told me roughly “learn how to suck a dick fag” and as he sat up I heard him say “show me your hole”. At first I honestly didn’t understand what he was telling me to do.
My head was spinning from what was going on and I kind of stayed limp and just let him push up against me and manhandle me around until I ended up in the middle of the bed on my knees. I awkwardly tried to undo my jeans while he was trying to pull them down. He pressed down on my shoulder as I got my belt undone. I felt him pull down on my underwear and then in an instant felt his big blunt tool pressing against me. Hard.
For what seemed like quite a while, I think I held my breath as I felt him trying to force himself into me. I heard him spit and he repositioned himself behind me a couple times but it didn’t seem to help. I know I was fighting it. The pressure against my asshole burned as he pushed and I know I squirmed away from him but he pulled me back and I tried not to scream. It hurt. A lot! There was nothing slow or gentle about him. In the midst of this I realized I was with a drunk horny college age jock with one thing on his mind. I could feel his fingers digging into my hips as he pulled me back against him. He wasn't nice to me and between the snorts and grunts he kept telling me over and over “take this dick, take this dick”.
I don’t know how long he actually struggled with my virgin ass but I know I was physically fatiguing and getting mentally numb from the pain. I started taking deep breaths and my girlfriend flashed through my mind. There was something about the pain I welcomed. It relieved the heart ache I had been feeling and kept me present. I pictured her face in my mind while I focused on the pain he was causing and I remember giving up at some point. As I collapsed forward, with my face pressed into the bed, I felt him pop into me.
I could feel his weight shift, pressing me down onto the bed as he bumped himself behind me. I remember the initial disbelief that I actually had a man’s cock inside me. I thought about my girlfriend getting fucked by someone else and tried to block out the burning his every movement was causing me. I repositioned myself a few times and eventually found that arching my butt up and keeping my chest flat on the bed seemed to lessen the hurt. It took a few minutes but it got better. I remember how good it felt once I was able to feel the full length of his stroke inside me. I felt wicked and sexy in a weird way, knowing I was giving an attractive hunk pleasure and I could tell he was getting into it.
He alternated between wonderful slow long strokes and faster pounding me down into the bed. The sensation that he was all the way inside me was something I won’t forget. Feeling his balls bouncing around behind me reminded me how small my parts were in comparison. He held a pretty firm grip on my hips occasionally pushing my shoulders downward with one hand and I remember the sensation of being physically overpowered. I know I had feelings that I had never had before. I remember physically surrendering and letting him move me around however he wanted. I felt submissive to him the way he was dominant and talked roughly to me but mostly I felt feminine with him as I wiggled my ass against him and rubbed my back against him when he leaned over me. I imagined how my girlfriends body moved and how she would feel to him in this position. I listened to his breathing and grunting expecting him to cum at any moment from the sounds he was making. The only thing he said to me the whole time was "take that dick" and asking me if I liked it. I kept answering him that I did. I remember him calling me a fag a lot.
I remember that during all this how small and completely shriveled up I was. I didn't get an erection or feel like I was going to cum but I was incredibly turned on and I remember my penis was flowing with precum.
He didn't last much longer and I felt him push into me hard and I could tell he was cumming. He stayed inside me for a minute longer and I felt his dick twitching as his breathing slowed before he let his cock slip out. He stood up and before I moved I heard him behind me zipping up his pants. He was out of the bedroom in under a minute and thankfully closed the door but I knew it wasn't locked.
I didn’t want to move and just stayed on my knees feeling exposed and slutty and used and strangely proud that my body had brought a man to orgasm. I could feel his mess leaking out between my ass and the cool sensation of his semen running down my leg. My girlfriend came to mind and I wondered if she was getting laid right then. I didn’t want to move but I got up slowly and made my way to the bathroom and sat down on the toilet. I heard drips of cum falling into the bowel and I farted a couple of wet messy farts. I wiped myself up before pulling up my pants and walking out to the bedroom. I had a new secret.
I walked down the hallway to the kitchen and looked around halfheartedly for my girlfriend. By the time I got to the front room I could feel more wetness between my butt cheeks. I walked past a couple sitting on the couch and made it out the front door. I thought I saw the guy I had just been with in a group of guys talking in the driveway and I started to panic. I didn’t know what to do but I made my way around the other side and walked as quick as I could down the street to my car.
I got in and before turning the key I took a deep breath and thought about what I had just done. I was glad for the impossible odds that anyone would find out. I thought about how surprisingly natural it seemed to be attracted to a guys body and how easy it was for me to touch him. I think I surprised myself. I thought about his thick hard cock. Sitting there in the car I realized I was turned on with how forcefully he had talked to me and how he had called me a fag. He had been a dominant, horny man. Feeling sexy for him as his more powerful body held onto me and moved behind me was new and weird. I liked the messy wet sensation that leaked out of my ass the rest of the night. The femininity I felt with him was new and intoxicating and I enjoyed these new feelings all the way home.
Looking back I realize I was angry with myself that I had allowed myself to be in a relationship with an unfaithful girlfriend for so many months. I was ashamed that my classmates and probably some of the girls in the school knew about my inadequacies. I was sad that I had not been able to physically satisfy the first love of my life. I felt humiliated and my heart ached for her. I know that for the first time in my young life I had now started fantasizing about the men, the bigger, stronger, better endowed men and the reasons my girlfriend was having sex with them.
In some weird masochistic way I guess allowing myself to be used by a stronger, bigger man made sense and the pain he caused me physically gave some relief from the heartache. He also permanently put the experience of such a heavy strong cock in my mind. Every time I beat off I compare my thin weak penis to what I felt that night. Obviously, I had no way to know what interests, attractions or experiences I would grow to have but looking back I can see a pattern of being humiliated by women love relationships in one way or another and then submitting to dominant men with my natural femininity to feel sexually worthwhile.
Not in any particular order or importance. I will add as memory allows:
Loosing my virginity at 15 with a slut at a party in a bedroom with other people watching me. I remember I was very quick and there was a fair bit of giggling and commenting going on.
Seeing the diary (a detailed list) of the sexual partners my highschool crush (first love) had had while we were together. I remember groveling with her about it. She denied completely. We stopped having sex but stayed together a few more months. All I wanted to do was cunnilingus with her every time we were together after that.
The first girlfriend who agreed to have a MMF threesome and the harsh reality of the guy she picked (young and athletic). Once we were in bed together she mostly ignored me and I just watched.
The first time a woman friend told me she thought I was gay.
The time a hot first date told me she was a lesbian while we were getting hot and heavy in bed after she saw my penis.
The time I got my GF an outcall massage and watched another man massage my woman for an hour.
The first time I went to a nude beach and exposed my little willie to random men and women.
The time my GF went into the bathroom with another guy at a party while I waited outside the locked door for 20 minutes.
My 5 year marriage to M:
The first time she asked me if I wanted to try on her bra and panties.
The first time I wore a bra and panties in front of her.
The time she told me she was willing to "play" (Be with other men).
The first time she dressed up and posed for me so we could take her "dating" profile pics.
The first time she started telling me what kind of porn she wanted to look at. Young and hung, BWC/ BBC, women and couples.
The times she told me in detail about her previous lovers and the fun we had as she teased me about my "interest".
The first time she knew I was wearing panties when we went out together.
The time she went into her daughters bathroom to get the tiny (toddler size) hair bands because the regular ones were too loose for my penis.
When I told her I wanted to touch some of the men I had watched her have sex with.
The first time I ever let her see me beat off and cum while looking at dick porn with her.
When my wife told me I should be completely shaved. Always.
The first time she wore an ass plug in public.
The first time I let her put an ass plug in me.
The time I watched her pull into our driveway (from upstairs) in a guys convertible and could see his hands on her legs.
The first time I knew I was eating another guys cum from her pussy after she came home.
The realization how many times I had previously eaten other mens cum from her pussy without knowing.
The moment she told me she had been sleeping with her last boyfriend on and off since we had started dating.
The first time she tried to put hair bands around me and they kept falling off when my balls retracted.
The first time I let her use a toy on my ass.
The day I realized why she had shaved her legs and pussy every single morning in the shower.
The time my wife saw me cum without touching myself while I was eating her pussy.
The first time M showed me her vibrator and fake cock collection and how intimidated I was.
The first time I contacted a man my wife had slept with and offered to come over for fun.. (It worked)
The time I helped a guy stroke off after my wife left for work, the morning after.
The first time a man saw me wearing panties.
The first time I watched her with a black man.
The first time a man watched me eat his cum out of her pussy as soon as he rolled off her.
The time she told me one of her girlfriends knew we we "playing" with other men.
The first time M told me to use her dong in her ass and she admitted her anal sex history.
One of our first "play" dates that I watched and listened to her with another guy from the loft overlooking the living room.
The time she sent me pics of her dressed up super sexy for a dinner when she was across the country at a business meeting.
The first time I watched her give a hand job to a guy in a hotel jacuzzi.
The time her eldest daughter dropped an empty TP roll on the coffee table and sneered at me as she walked away.
When she admitted her preference for young men.
When she slept with 6 different college guys (one at a time) from the local college over the course of a few months.
The first time she entertained two guys during the same evening.
The first time she saw me touch another guys cock.
The first time she watched me suck another guys cock.
The first time she told me to eat a guys cum off her tits.
The first time I saw her tell a "play" date to beat off for her and how she humiliated him. (She declined having sex with him).
The first time she teased me while sunbathing at a hotel pool knowing I was watching her flirt from our room window.
How things changed (how she changed) after her daughters had both moved out of state for college.
The first time I bought airfare for a guy she had met online.
The first time one of her girlfriends saw me in panties.
The time since...:
The times I have called some of the men M slept with while we together and offered myself. (I've been with about 7 so far)
The first time I went to a man's house fully dressed. ( bra, panties, dress and sandals)
The times I have met men who were traveling in hotels for submissive sex.
The first time I met a young (20 y/o) black guy and I jerked him and let him cum in my mouth.
The first time I was afraid with an Alpha male. He was the most forceful so far.
The time I cleaned house for a guy wearing panties and a bra.
The first time I was with a black man (stroking and blow job)
The first time I let a black guy fuck me.
The first time I took a guy bareback and had his jizz leaking out of me all the way home.
The first time I was fully dressed for a black man.
The first time I was with two black men at the same time.
The first time I let a guy take pictures of me dressed and sucking on him.
A good place to start, a little about me.( to be continued…)
A good place to start, a little about me. (I will add more if encouraged)
I am 53, educated, professional, and fairly successful. I am definitely not egotistical or vain but have been given enough feedback over the years from men and women to feel lucky to be physically attractive. I lost my virginity at the age of 14 and have been intimate with over 125 women and about 50 men.
My first memories of arousal were as a 9 year old with my older sister and one of her girlfriends. My sister would have been 15 and her friend about the same. My mom was gone and they were baby sitting me and somehow they got me dressed in their bras and panties and paraded me around the house. I remember the laughter. I also remember they took me down to the swimming pool (in public) and when I got out of the water they made a big deal out of my penis showing through the panties. I remember them both pretending to dance with me and trying to get their arms around me. There was a lot of laughing and poking at me and I remember having an erection and being embarrassed.
