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Never Say Never

I am an older man, I'm 64 and I am single, divorced for over 10 years and I live alone since my children are all older and on their own. Over the years after being in a sexless marriage and dating Women who were not interested in sex my thoughts turned to fantasizing about doing things with other men in the same situation as me. So eventually I started getting on different sites and managed to find quite a few men who wanted to meet but in the end all were no shows. I was so excited and nervous at the same time then after being let down instead of getting frustrated the desire got even stronger. I knew of an Adult book store not far from me that had video booths and a gloryhole also. I kept thinking about who would go there and knowing it was very risky to say the least but never the less I past by there many times and eventually went inside. It was actually a nice place in a nice area but there were always a lot of people inside so I just looked around bought something and left. As I drove away I admitted to myself that I wanted to suck another man and I needed to get brave enough to take the plunge. So one Snowy Monday morning I took a ride by and there was only on car there, I quickly parked and went in and only one man was there looking at magazines. An older well groomed man maybe a little younger than me. I went to the desk got plenty of tokens and headed to the booths as he and I made eye contact. Between booths 4 and 5 there it was a good sized gloryhole in the wall, at that point the excitement grew as I put the tokens in the machine and turned the sound way down and waited. In a few minutes the door on the other side opened and closed I heard the token being put in the machine by the same man I saw. I'll be honest I have read about gloryhole etiquette and I ran my finger around the hole and In a matter of maybe a minute I was on my knees watching this man taking off pants and underwear. He played with himself to get ready and then he stuck his hard cock through and without hesitation I licked the head and waves of excitement ran through my whole body! I move closer and slowly took all I could take in my wet mouth, it was what I was waiting for! I could hear him tell me to hold still, which I did and he started fucking my mouth and then I heard the groan and held still as he held still and felt the sensation of his warm cum filing my mouth, he pulled out quickly and I spit out his cum as he hurried and dressed and left. I waited for a few minutes and then left myself. To my surprise he was outside waiting in his car and as I walked by he motioned for me to come over and oddly enough said thank you and I thanked him also and said it was my first time. I t was cold as hell so I said I had to get warm and before I left he handed me his card with his cell number on it. I knew this wouldn't be the last time with him, At least I hoped not. Never thought I'd see the day! Never say never!


    I watched porn and my focus was on men doing a mutual, that was an immediate turn on, I would watch and masturbate. I really wanted to have a jack off buddy. I watched cock sucking porn and again my desire for cock only grew, it was on my mind all the time. I found a site where one could let others know what they wanted to do. I met a guy named Dave, I asked for his phone number so they we could talk first before meeting. He gave it to me after I told him that I was in the transportation business and came to this town ten times a month. Dave was eager to meet me, I was nervous as I never did this before but wanted cock sex. I told him that I am not gay, guys don't attract me, it was the cock that I wanted to love, he was the same. He told me that he was looking for someone to do mutual masturbation with and cock sucking. We spoke several times, then one day I told him which hotel I stay at and when I arrive that I will call him, Dave told me this hotel was only 20 minutes away.
    So when I got there I called him, I took off all my clothes, my cock was so hard as I ran my fingers down my shaft waiting for him. Finally a knock on the door, I let him in, as he looked at my nakedness and stiff cock. We went to the couch and sat down. In the meantime I was gently rubbing my cock as we spoke, Dave kept his eyes on my cock, I turned towards him for a better view. At this point he reached over and ran his fingers my cock, it was an electrifying feeling as he did, then he held my cock and masturbated me. He stopped and stood up, he took off his clothes, his cock hard and I wanted to have sex with it. He stood there starting to masturbate his sexy cock. Man Just got harder. He moved in between my legs sideways, up to the couch and slowly turned towards me as I was leaning forward. His cock was on my cheek and slowly moving towards my mouth. At my lips his precum was getting them wet, I wanted his cock and he knew it.
    I stayed in a suite which has a bedroom. I stood up and told Dave to go to the bedroom where we could be more relaxed. As we walked I grabbed his cock handheld it until we were on the bed. I told Dave that I wanted to masturbate and suck his cock. He smiled as he masturbated me. It was just like my fantasy, Then he started to suck on my cock, man he was great. He pulled off and laid back with his cock hard and so sexy as he moved it. My mouth drooled at the site of it, I reached over and gently masturbated him, Then I leaned over and started to lick his head and shaft and then my lips and mouth went over and his cock was in my mouth as it went in deeper along my tongue I knew that I was loving cock sex. I sucked him as best that I could, if it went in too far I would gag so I worked on his head, my tongue would lick him and French his slit, below that I would masturbate him. When Dave saw that I was sucking him well, he got off the bed and stood up, telling me to get on my knees and suck him there, so I did eagerly. Know his cock was all mine and I loved it. I licked his balls as they wiggled away, then I would lick his shaft to his head and mouth his cock. He pulled out as his cock was moving up and down and wanted to cum on my face. He didn't as I sucked him more, then I could feel him quiver and his cock move up in my mouth as he blew his load in my mouth. I kept sucking until he stopped cumin. His cum was warm creamy, a bit salty and not bad tasting. I opened my mouth for him to see his cum as I swallowed it. I went back on his cock and sucked any cum that was left. We went back to the bed, Dave was happy and me still horny as hell.
    We talked some more about our well our encounter went and that having his cock sucked was so hot. He reached over and grabbed my cock, I melted by his touch, Dave knew that I was all his at this moment, as he masturbated me I was in heaven. Then he sucked me off. I lasted maybe five minutes and blew my load in his mouth as I held his head down as I thrust my cock deep into his mouth, finishing I let go of his head as he pulled off.
    We talked some more about our cock sex, I didn't want to go further with him, I know that he did as he tried to kiss me, sometimes we would as we were so horny and I know that he wanted to fuck me all that he got was his finger in my ass as I cum. Enjoying a cock I found it to be sexy like a woman, her curves, breast, c**t and now for me cock is added to the list. I have wonderful sex with my wife as well.

    Dads Boyfriend

    Saw a post below about a guy with a gay dad who turned him gay. My dad also went gay after divorcing my mom, but he was the opposite. He was masculine and definitely the boy of his relationships. He would have liked you and your dad. His boyfriends were always younger and feminine.
    There was a little spillover though. When I was 18 I was at his house for dinner. His boyfriend was a 20 something guy named Jeremy. Dad needed something from the market and made a quick run. As soon as he was out the door Jeremy asked me if I could keep a secret. When I said yes he told me he wanted to suck my dick if I wouldn't tell dad. As a very horny 18 year old I said why not. I unzipped my jeans and took out my dick. He got on his knees and sucked me like I never had before. It only took a couple of minutes to cum in his mouth.
    I let him suck me whenever we got the chance but I never did anything to him.

  • Trained To Be This Way

    My dad basically trained me to be gay. And not just gay, he pushed me to be a sub, sissy, I guess when I was around 5 my parents divorced because dad came out as gay. On weekends with dad he treated me like a girl. He dressed me in girls clothes and I just remember his attitude that "guys like us have to please real men". I heard that over and over growing up.
    As you can understand my mom kinda hated dad for embarrassing her. Around the age of 11 or 12 I started to display some of the signs I was following in dads footsteps. Mom didn't like that and sent me to live with dad full time. I barely saw her after that.
    As for dad, well he started treating me more like a roommate. He was very open with his sex life. I saw many men in and out of the house, but there were a few that were there a lot. At first dad would at least go into his bedroom and shut the door but I could still hear what was happening. Around the house our usual lounge wear was pretty much a pair of panties and maybe a t-shirt. Around age 14 I started to actually see how the men were looking at me. They had been looking at me for awhile but as I got older I understood what was going through their minds. One guy in particular started to openly talk about me in front of dad. Dad was OK with it as he was very sub and only wanted to please this man. It was at that time I witnessed my first gay sex act. This man made my dad give him a blow job right in the middle of the living room as I watched. After that dad really seemed to push the "guys like us have to please real men". He stopped shutting the door to his bedroom and I saw a lot of things happen.
    I guess right around that time I simply accepted it. For awhile I had been avoiding the attention I was getting at school from a few boys. I gave in and began to accept their advances. I was kind of funny seeing these so called straight boys with girlfriends sneaking around to get me alone. I started giving regular blow jobs to several boys and I was actually enjoying it. I told dad what I was doing and he seemed kinda proud at my behavior.
    I was now 15 and a freshman in high school. One evening dad hinted it was going to be a special night. The man I mentioned earlier that seemed to have an interest in me came to the house. After a few minutes dad came out of the bedroom and told me to come with him. He led me into the bedroom and the first thing I saw was this man laying on the bed naked with his cock sticking straight up. He was bigger than any of the boys I had been with so far. Dad told me it was time I learned to please "men". I was OK with it, so I got on the bed and started sucking his cock. It was different than the boys at school. This man grabbed my head and was very rough trying to push his cock down my throat. He started manhandling me around the bed until he had me face down. He pulled my panties off and started probing my asshole with his lubed fingers. I spread my legs wide to give him access. He suddenly grabbed my ankles and pulled me to the side of the bed so my feet were on the floor. It was rough as he started pushing his big cock inside my virgin asshole. Dad actually watched as this guy fucked my ass. From that point on I started having sex with several of the men that came over. Its kind of strange thinking about it but I never had any sexual contact with dad. All through high school we saw each other have sex openly and even allowed 2 (or more) men use us at the same time. But we never had sex with each other.
    I am still a sissy and love pleasing men no matter what they want.

    The Most Amazing Man Came Into My Life When I Needed Him

    I was left orphan at 13, and went to live with my maternal grandmother. She was, although I didn't know then, a bitter old lesbian. My grandfather, her husband left her soon after they were married. Those years when I lived with my grandmother were the worst years of my life. At 18 I left, that day, went to stay with my best friend from school. I never spoke to my grandmother again. I only found out of her lesbian bitterness after she died. She left me her house, as her only heir.

    I used the money from the house to go to college, I went to work for a Global CPA firm after graduation, became a CPA, moved on to a job in industry, bought a small townhouse, lived alone. I was accused of being a lesbian, for befriending a girl in my department.

    Out of the blue, left field, a man stepped forward and quashed that line of accusation. He, a man of overwhelming influence, came to my side. I met him later, at a lunch. He was the most impressive man I had ever met. He drew me into conversation, I assured him I was not a lesbian. I was seeing a man, a black man.

    In the car he turned to me, asked if I really meant for a black man to penetrate me, to leave his seed in me. I forbid it, he told me. Do not fail me, he said. A woman's virtue is her obedience, he told me. If I was lesbian? I asked him. I will take care of you, he answered. So I can be a lesbian? I asked him. If you must, he said. Nevertheless you will carry my children. I carried his children, cared for him and his children. Made a home for him and his children.

    He never interfered with my relationship with my girlfriend. She was protected, she grew in her career. He oversaw her personally for a few years before putting her in a position where he needed her. If it happened that she joined us for dinner, or maybe went with me and the children on a long weekend, or he saw we needed a few minutes of privacy in the kitchen, he looked the other way.

    He is retired, he has his following, important people looking for his opinion. I think about my grandmother, why was she so bitter? What she was didn't fall far from the tree. Maybe her husband didn't allow her, maybe she couldn't face him, maybe somewhere she disobeyed him. The person in her diary, her letters, kept her distance. He left her, never divorced her. When he died, she was his widow.

    My husband, he is different, still the most impressive man I have ever met. He knows, knew that day in the car, there was never a man, except him.

  • I Might Be Obsessed

    Happily married to a great woman, we have 2 kids and a great house in a beautiful neighborhood. Jen works a prestigious job in the city, and I do well with my firm. My problem? About 3 months ago, the cleaning service we have used changed hands, and we have a new crew. Each week, 4 Hispanic women come and do a full cleaning of the house. They have the code for the door and alarm system, and always do a good cleaning, well worth the money. About 3 weeks ago, the baby monitor in my daughter’s room sent a motion notification to my cell, and even though I knew it was the cleaners, I check the camera.
    There in a grainy black and white video was a beautiful younger girl, dancing as she cleaned, listening to her earbuds, not a care in the world. Definitely curvy, totally different than my slender and fit blond wife. I felt compelled to watch until she left the room.
    Since then, I upgraded the monitor to a newer camera and audio recording system, capable of storage and higher resolution color video. I have watched the 2 videos I have multiple times, usually when I’m home alone and can please myself uninterrupted.
    I find myself thinking about a woman whose name I don’t know, whom I have never met, and fantasizing about what I would do to her.
    My wife has been the recipient of some very ardent love making, and I have to be careful not to let on that I’m thinking of someone else.

    I’ll probably never meet or act on my fantasy, but I can’t keep her off my mind.

    Early On In Prison, I Found My Calling, My Profession

    During my teen years we went around and if we found something that wasn't nailed down we stole it. We were what was called then, juvenile delinquents. I dropped out after the tenth grade and got a job as messenger boy for this outfit (read criminals). I knew the city and could get in and out of almost anywhere. I picked up things now and then that the owners later said was theirs, but I was chump change for the cops, they didn't care. Until I was 18, and I got busted along with another guy, this time for grand theft auto. We borrowed it your Honor, we were going to return it. We got five years, three and probation.

    I walked out of the big boy school with a limp and lighter in the shoes, if you get my drift. A boy had to pay his way, and men are locked up in there, and boys are fresh meat. I didn't fight it, I went queer immediately, I made his bed and licked his ass clean, I sucked his cock, and took it like a man straight up the ass. If he was in the mood for kissing, well I kissed him too. I made sure he liked me. I got out, I was 'turned' as they said, I was into 'it', I enjoyed it. Well sometimes the truth comes out. I became a boy working for Angelo, old men who paid for it. I was good and made good tips, and after a few years I had a nest egg.

    I got on a Greyhound for Florida, where my man lived and he was out and I went to see him. See, he was as queer as I was, except he was the Alpha and I was his Beta, and we plugged in together. I kissed him, and hugged him and sucked his cock and let him fuck me, except this time we were alone in a trailer. We could be as naked as jaybirds, and we had time on our hands, and lived off of my nest egg. When it came time to make some money, I hooked up with Arturo, who serviced the men in the high rises. I wore the suits, and the shoes, and I sucked and fucked and got paid for it. Old Jews from Jersey, and old Italians from Philly, and Old Mexicans who came up from Mexico, What they wanted was a boy to service them, and that was my specialty.

    Well let me catch up to today, I'm of course not a boy anymore, I like having a boy around myself, but at one point I had to quit and start my own business. I got along well with Arturo and he had me run the boy trade in Tampa and St. Petersburg, new condos with newcomers from Canada and Chicago. I ran some black boys too, and a few Cubans. But my clientele liked white boys, skinny boys, with tight asses and pink panties. I made a lot of money.

    I'm living in a nice place, retired, I have a boy who hangs around and I suck his weenie, and lick his ass, and let him fuck me. That's me, I need a boy around, one who rides my back when I need it.

    Get Me Wet, Tell Me About It, I Want To Hear It

    I'm a regular here, I love to read about girls, it seems that a girl's experience is what I can identify with, I can't say that about men. As a girl, I've been fucked. I don't believe in girls talking about fucking him or her as the case may be. Girl's get fucked, and the boys do the fucking. I'm old fashioned in that way.

    When I was in school it was very strict really. There was a lot of separation between the boys and girls, and things happened but it wasn't that often. If you compared the boy stories to the girl stories, they boys were exaggerating. But every girl knew that her day was coming. Some made themselves ready for senior prom, other's who were dating a ball player got nailed in the back of a Buick. Most of us weren't getting any until we got married, and we didn't necessarily agree with that. We just weren't attractive enough for a jock to fuck us behind the bleachers.

    I had to wait until I got married. My husband was a Navy guy, and he had a lot of experience. Nurses and local girls in ports of call. Sure they were whores, but they had pussy. When it came to me he didn't even know where to start, how to get me hot. It was a cold night that night, it hurt and he didn't apologize. It was more than disappointing. He was used to girls who were hot and knew how to get it on, I wasn't.

    But I read books about girls, some about girls who went out with girls, but a lot about girls stolen in the middle of the night by pirates, or sheiks, or bad men. How they squealed, but they were done for, there was no escaping. Their day came that way, my day came the day I got married, not that I care to remember.

    My husband went out on maneuvers and was gone for several months at a time, that left me home with my finger. I started to think of ways to pleasure myself while I read about a girl lost in the jungle, at the hands of cannibals. I dreamt of them, while I fingered myself, and later with the help of a sex toy I bought mail order. By the time my husband got back I had more experience, and I got wet enough and he got off with me. It ended up as expected, I mean expecting. Kind of late, everyone expected you to be pregnant right after marriage.

    So I come here to read about girls, and what girls want, and what girls feel. Some of it is fantasy like the novels, that's ok sometimes I end up with my finger in me. Other's I read and their is a thread of truth somewhere. I know that some of the girls here have been the taken by force. But in the end we all have one thing in common. We got fucked.

    And that's what I'm looking for. I love to hear about it, to feel what she feels. I have watched girls on the internet, but that isn't the same, tell me how you felt that day, when it was going to happen and you were powerless to stop it. If you were dragged behind the bushes, or if it was a boy in your dorm room, I want to read it. What was it like for you that day when he fucked you.

    He's No Mike But He's My Baby Daddy So I'll Keep Him

    The first part is the back story as to how my boss and me talked about sex. And what happened after that.

    My college sorority sister married Mike right out of school. He is blue collar which surprised every one, granted he was a first class hunk of a man. Charlotte bragged about his prowess, yuck to me. She got pregnant out of the chute and went back to back with her second son. We got descriptions like when he had sex with her she could feel his, mmhm, in her throat, and every knows how deep he goes determines whether a boy or a girl, so he went deep in her. We listened, embarrassing, but she was proud, he could go all night.

    The boys were two and three when Mike was in a work accident which left him paralyzed from the chest down. Gone were his job, his manly presence and sex. She and me were always close, she cried, nothing could replace his manly presence, and now he was in a motorized wheel chair, going through rehab and being retrained for a desk job, telephone inside sales. Charlotte felt she was going to go dry, so young and her only contact was being his nurse, he had no sensitivity, only anger because he was no longer a man like he used to.

    I confided in my boss, without her permission. To me yuck, but my boss told me not to knock what I didn't know. Some women like it even if it was yuck to me. Around about when Mike's condition was clear, irreversible, and demoted to inside sales, my boss told me he wanted a piece of my ass. Think hard about it, no pun intended, he wasn't taking no for an answer. Time for me to give it up.

    He wasn't Mike, he was himself, and with my ass in his hands I got the round the world treatment, and walked around the next day still smarting from the ass fucking he gave me. I called Charlotte, what did she do, how did she take it. Use my finger to get wet, and spread out so he has complete access. If I was taking it up the ass, have him fuck my V first to loosen up, men go further and deeper in your ass so keep that in mind. Had I thought about giving him a blowjob first, and work down his libido?

    Nothing worked, I was sore from him fucking me, Charlotte recommended exercises to become more limber, and if that wasn't enough have him go see her, by the time she was through with him he'd be a pussycat. Yuck, double yuck, send him to see her? But Mike was where he was, and he wasn't changing, and Charlotte needed some attention. Out of loyalty to her I brought it up, and my boss 'did' her. Not Mike mind you, but better than nothing. When I popped out a girl, Charlotte smiled, she knew it. My baby daddy wasn't Mike, he's okay as far as it goes, but then again I didn't know no different.

  • Starting To Enjoy It... A Lot! (Part 1)

    I have confessed on here before about my live in girlfriend (call her Lisa) being trans. Further that I occasionally bottom for her.

    To add some context we dated then moved in together a few months later. Lisa is very attractive, passable and fem. One night after sex we were talking about our sexual exploits and Lisa admitted something. She told me that even though she lives life as a girl, she still has occasional boy urges. Lisa came out and asked if I would possibly try the bottom side. I had never done that before but said I would try for her. I knew Lisa was on hormones and erections were difficult. She admitted that her doctor had previously given her a prescription for industrial strength little blue buddies to over ride the hormones. Well the next night we did it. That evening she fucked me in the ass twice. Lisa isn't small either, she has a respectable 7 inches. I was quite sore for a couple of days but it wasn't bad.

    From then on when she got in a boy mood I would spend a day or 2 on the bottom end. Lisa really started getting into it. Every time she seemed to get more excited about it. And I have to admit I really started to like it myself. So much so that last Saturday morning I surprised Lisa. I got up early and got ready. I went into the bathroom and put on some of her makeup, especially bright red lipstick. I had bought a pair of lacy panties and put them on. I walked into the bedroom and took her breakfast in bed. A glass of OJ and a couple of her little blue buddies. She was definitely surprised, but I could see she loved it. We laid in bed, made out and played around. It took about 40 minutes but I started to feel her beautiful cock start to perk up. I immediately started giving her the sloppiest head I could. Lisa had a grip on my head and was bucking her hips. Finally she couldn't take it anymore and pulled my mouth off her cock. I rolled over on my stomach as she pulled the panties to the side and poured lube in my ass crack. She got me good and ready with a couple of fingers and finally mounted me. I was in heaven! She wasn't gentle and fucked me good and hard.

    I wore the panties all weekend and and she took the aggressive top role. Lets just say she fucked me multiple times all over the house! And as a bonus this little surprise of mine opened things up. We did a lot of sex and fantasy talk. Turns out we are both open to trying some kinky things. The first thing on our list is to try and have a 3sum in the next couple of weeks. We are discussing 2 options. Maybe finding a masc dom male to take both of us. Or maybe a sissy gay guy or another trans for both of us to use.

    I will throw a part 2 out when we have our first adventure.