[M]y first and last ti[M]es with a [M]an | 2016

I haven't been a part of this reddit for long, but I thought I would share an experience I've had, that I haven't really spoken about since it happened.

I've always been straight. When I was younger some things were presented to me that I wasn't fully aware of at the time, but it left me with a curiosity that stayed with me despite having long rewarding sexual relationships with women. I have plenty of those stories, but this story is quite possibly the weirdest, and strangest thing thats happened to me.

I was 19, just out of highschool and I had two jobs. One was at a grocery store, in the mornings I delivered papers around the city. I delivered to many apartment complexes, old folks homes and assisted living communities. The last deliveries I had to make were to a completely indoor assisted living community, and I dropped the papers off anywhere between 4 and 6AM.

One morning I was walking around dropping off papers indoors when I saw an elderly guy walking slowly down the hall. I thought nothing of it until I saw him stagger a bit and as I passed him I could tell that it wasn't due to his age but the smell of alcohol was strong enough I could smell it as I passed. He staggered a bit and I stopped and turned to him to make sure he was okay.

"I'm sorry" he said a few times "I'm just trying to get back to my apartment". I asked if he wanted help and he looked at me for a moment and then said, "Yes, that would be nice"

I walked beside him, my arm around his back but not holding him up. He seemed to be fine walking with me next to him as he would say "Its this way" or "Its just down this hall". When we reached his apartment, which was one that wasn't on my route, he fumbled with his keys. He handed them to me and said "Can you please help me in?"

I did and asked if I could help him in his room. I walked him in and he asked if I could take him to the bedroom. He leaned on me as I walked him over to the bedroom and sat him on the bed. He asked for a glass of water and I told him that I had to get back on my route and that maybe I should contact someone from the assisted living place and have them tend to him.

He said that they wouldn't help him because he was drunk. Either it was my naivety or just that I wanted to help, but the older man convinced me to go to the kitchen and get him some water.

When I returned he was standing at the side of the bed. He removed his wallet and cell phone from his pockets and put them on the nightstand. Then he began fumbling with his button on his pants and his belt. As soon as he was able to unbuckle them they dropped to the ground and he tried to kick with his legs to get them off, but his shoes were still on and he couldn't get his pants off.

"I'm sorry my boy" he said "I'm sorry, I can't, can you help?" He sat back down on the bed for a moment and I walked over and we made light conversation about my paper route and how tough it was to work two jobs as I began taking his shoes and socks off. I leaned down and noticed he had very thin stick legs and a wiry frame.

As his shoes came off he braced himself on my shoulder and stood again so that he could lift his legs out of his pants, but at the moment he stood, he kind of leaned forward and thats when I first felt it, something kind of hard as it tapped against the top of my head.

At first I thought it was his hand or something, but as he steadied I looked up an saw that his boxers were unbuttoned and sticking through just slightly was the head of his erect cock.

Thinking to myself I wouldn't make a spectacle I averted my eyes and looked back down and asked him to lift one foot, and then the other so that I could remove his pants.

As I fiddled with lifting his foot as he stood I looked up at him and he was smiling at me with a glassy eyed look.

"You're a good boy" he said to me. I remember that because he repeated it. I felt his warmth lean closer and I took notice of his cock again, it had grown a bit more outside of his boxers and I could only imagine that he took notice that I saw it and didn't look away.

His hand rested on the back of my head and I remember thinking "I need to get up and leave" but I could feel his hips nudging closer and his hand on the back of my head stayed firm and comforting as he rubbed the back of my neck and repeated "you're a good boy."

The next thing I knew his cock was pressing against my lips. I looked up at him. I pulled my head back a bit, but as I did some precum stayed on my lips and I licked my lips as a reflex. His hand on the back of my head kept rubbing softly and I leaned forward again and kissed the head of his cock again.

I knew what he wanted and I knew what to do as it had been done to me many times before, but it was weird doing this to someone else. I parted my lips and took the head of his uncut cock into my mouth. I began to lick as far down as I could until the boxers wouldn't allow me to lick anymore and I would lick back up to the head and take him back in my mouth.

I closed my eyes and began to suck as I felt his cock slide deeper into my mouth, to the back of my throat, but not far enough to gag. I kept sucking until I heard something. It was a click.

I looked up and he had picked his cell phone up from the nightstand. It was an old flip phone and he had just snapped a picture of me sucking his cock.

I didn't think much of it... this was a time where smart phones weren't popular, I didn't think about it getting out or online. I took his cock out of my mouth and pumped it a few times and asked him if it felt good.

He said it did.

I took his cock back in my mouth and used my hand against his shaft as I sucked until I felt it get harder and hotter. He put his hand back against my neck and began pulling my head onto his cock as he moaned softly.

Within seconds I could feel his come shooting in spurts against the back of my throat.. then onto my tongue. I just swallowed as much as I could and kept sucking until there was no more salty cum dripping onto my tongue.

"You're a very good boy" he said. He sat down on the bed and we kind of talked a little bit about what happened. Thats when things went from strange to bad.

I asked him what he planned to use the picture for. He told me that he wouldn't use it for anything, if I came back tomorrow and did it again. If I didn't he could send it to someone in the complex and say that I took advantage of him when he was drunk.

I began to shake nervously. I got up and he told me to relax. He said just to come back tomorrow, and do this one more time and if I did he would delete the picture and I would never have to see him again. I agreed.

The next day was where things really took a turn.

When I returned the next day, it was on a weekend and I didn't deliver on weekends, that was another guy from the paper. I did have the code to get in the gate and made my way back to his apartment.

When I knocked on the door it was opened by someone else, not the elderly white man I saw before, but an equally elderly black man wearing a robe. He told me to come on in and that the white guy, Mr. W. was in the bedroom and he showed me in.

I was shaking uncontrollably. I was only 19 and freaking out. I had never done anything like this, and somewhat prone to anxiety. I had sucked a cock my first time yesterday and while I did enjoy it for what it was, I wasn't comfortable with this situation.

Mr. W. saw me and smiled. He told me he wanted to try something different today, nothing more than me sucking him off, but he wanted the black guy, Mr. B. to watch. He also had one more request. He wanted me to take a shower and be naked except for a few of the items he wanted me to wear.

I told him no. I told him I would shower, and take my clothes off, but I wouldn't wear anything like handcuffs or bondage. He assured me it would be nothing like that and that I should go shower as they needed time for the medicine to kick in. I assumed they meant viagra or something similar. I went into the bathroom and showered as he asked.

I came back out, and he had a pair of thigh highs, a thong and a straight blonde wig.

We argued for a little bit as I stood there with a towel wrapped around me. He said he just wanted me to dress up as I sucked him because Mr. B. had a thing for watching live girls and this was for him.

They talked me into it after about a half hour, I put on the black leggings, the thong which may have been for men, it seemed to hold all of my parts in place, and the blonde wig.

Mr. W. laid back on the bed in his robe and unbelted it. His erect cock stood at attention and he beckoned me over. I crawled up onto the bed, my arms and legs shaking from nerves. I wrapped back hand around the base of his cock and began to stroke him.

"Just like that" he said. I looked up and noticed for the first time he had dark grey hair.. i never paid attention to him before. "Put my dick in your mouth honey" he said. I lowered my mouth onto his cock looking to the side to see Mr. B. stroking his cock and watching me intently.

I looked up at Mr. W. as I sucked, he looked down at me and then at Mr. B. "Can you see her?" he asked him. "Come take a better look".

Mr. B. got up with his erect cock, which seemed larger than Mr. W. but not as big as Porn Movies made me believe a black cock would be. Mr. W. was smaller than I was at probably around 5 inches.

I closed by eyes and bobbed my head down again taking as much of Mr. Ws cock in my mouth as I could, and was almost able to take him all into my mouth.

My shaking began to subside when I felt Mr. B's hand touch the back of my head pushing me deeper.

I fought his hand and came back up by kept my lips on Mr. W's cock.

Mr. B was behind me.. and I felt his hand rubbing my back and Mr. W. reaffirmed that it was okay to touch me, despite me trying to shrug off his touch.

I refocused on Mr. W hoping to make him cum. Partially because I wanted this to be over, but also because I wanted to taste it again, if anything it would be for the last time.

Mr. B suddenly reached around and his rough hand brushed against one of my nipples. I kind of winced for a second, but he began rubbing one of them and pinching it slightly. I don't know why but I began to get an erection.

"She likes that" Mr. B said.
"She likes my dick" Mr. W said.

At the moment neither of them were wrong. I redoubled my efforts, using my hand to jack off Mr. W. Mr. B repositioned himself to my side and his head lowered. He took one of my nipples into his mouth and began to suck and lick. I was mostly hairless except for my legs, but stockings were covering them, I could only imagine that licking me was similar to what I've done with women that were A cups, something that was common in my early highschool years.

Mr. B licked on them and reflexively I put my hand on the back of his head and made a little moan when he bit softly.

My blowjob was getting sloppy and Mr. W. asked if I could lay down and he would "Feed me" and I was turned on and just did as he asked.

I laid on my back and Mr. W positioned at my head, Mr. B positioned at my chest, both their cocks hard and ready and I began to feel lustful and willing to please them. I reached for Mr. B's cock and began to stroke it as Mr. W pushed his cock in my mouth and I let out a moan.

I could feel Mr. Bs cock was slick with whatever he was using, possibly vaseline as I stroked it.

I was so turned on and they both took notice. This actually opened me up to nipple play with women in the future which still can turn me on.

Mr. B was on his knees with me stroking his lubed cock, Mr W had his hand on my head and pulled my mouth on his cock as he used my mouth for his pleasure.

Mr. B began to finger my nipple and slid down lower to the thong. I was erect and popping out of it a bit, but instead of feeling his grasp on my cock, he went below my balls to the string covering my ass and he moved it aside.

He began rubbing at my hole and I squirmed. I began to lose my erection as I started to worry about what he was doing, I had never really had that done to me although I had tried anal in highschool but the girl had done it before.

I moved a hand to Mr. Bs but Mr. W stopped it with his hand. He wasn't stronger than me, but he had a weight advantage due to his position.

Mr.B played a bit and it didn't hurt. His fingers still had some vaseline on them and I felt him play a bit until it felt almost slick. He pressed at the opening and that was when my legs began to close. Mr. B repositioned himself. He was no longer at my side, he had straddled one of my legs so that I couldn't move it.

I still had Mr. Ws cock in my mouth but I wasn't moving and neither was he. I just held his cock there, eyes wide as Mr. B pushed his finger into my ass. "Be a good girl" Mr. W said.

I teared up a bit, and looked up and saw Mr. W looking back at me.

Mr. B finally got past a point from where the pain was terrible, to where it felt good. The deeper he pushed the better it felt so I succumbed to it and stopped trying to clench and keep him out, it only hurt more.

Mr. B began to pull his finger out and push back in.. slowly. I relaxed my legs and he felt it, so he move himself back to my midsection and clamped his lips around my nipple as he finger fucked my ass.

I began to enjoy it a little. "See" Mr. B said. "It feels good. Don't be afraid. It feels good." Mr. W began pushing his cock back and forth into my mouth again.

I closed my eyes, a tear rolled down to the bedspread below and I began to bob my head and pleasure Mr. W as much as I could to make him cum as Mr. B did as he wished with my ass. It felt very good but as he wasn't touching my cock I didn't feel like cumming, I just dripped precum onto my stomach and kept quiet, only moaning when Mr. B nibbled my nipples a certain way.

When I felt Mr. W getting harder I knew it was going to be over soon and I began sucking harder. "Look at me with those blue eyes baby. I love blonde hair and blue eyes" Mr. W said and I looked up at him and he pumped my lips a few times and I felt his cum begin to fill my mouth.

I moaned as I sucked his cock of everything I could, feeling horny and ready to cum myself, but also happy it was about to be over.

I didn't realize that Mr. B had edged himself to my opposite end.. his finger only pressing against my ass as a placeholder for what was about to happen. I had all just finished sucking Mr. Ws cock to completion when I felt Mr. B pushing the head of his cock slowly into my ass.

I still had Mr. Ws cock in my mouth 4 inches deep when I felt Mr. B pushing into me and pulling out of me slowly, creating a larger hole and jolts of pain returned as I clenched tightly.

He pressed harder with his cock inching deeper each time despite my protests until I remembered it hurts less to just give in. As he pulled out the last time I unclenched as he pushed his cock into my lubed ass once again, this time with the result he wanted and he burried the head inside me.

I had no clue if he was wearing a condom or not, but I would learn later that he did have one on, thankfully.

Mr. W pulled his softening cock from my mouth just as Mr. B pushed himself deeper inside me. I was finally able to look down to see the older, slightly thicker, bald black man hold my thighs open as his cock pushed in and out of me.

My mind raced as I fought to keep control of my legs, but as Mr. B held them up and my legs began to tire from holding them I let him hold them as he fucked me slowly, pushing into me deeply and pulling out.

After what felt like an eternity I noticed it felt very good. He began sliding in deeper and the deeper he went the better it felt. I began to get semi erect as Mr. B fucked me at a steady rate. He dropped one of my legs and I repositioned so one leg was down and the other was held at around his shoulder, with my knees bent as I wasn't very flexible, but it didn't stop him from fucking me with his entire length.

I didn't notice but at this point my blonde wig fell off as my head was rubbing against the bed, and even though I looked more like a man in stockings and a thong pushed to the side Mr. B said to Mr. W "she feels so good" before he finally pushed me over for one more position. I got on my hands and knees and Mr. B pushed his cock inside me and grabbed my hips.

In that position it was the first time I truly felt like I wanted him to fuck me. I don't know what it was but I met him when he thrusted into me, I leaned back. Despite the entire process from him entering my ass the first time to when we got into the doggystyle position was only about 5 minutes or so, I began to feel horny enough that I wanted his cock. The pleasure was intense when he fucked me and his hands were on my hips pulling me onto him.

Mr. W positioned himself at the head of the bed and took the wig and placed it back on my head. He watched my face intently as Mr B fucked me for my first, and last time. He leaned in and grabbed my face and tried to kiss me. I turned away as for some reason I just didn't want to kiss him.

He then got on his knees and put his soft cock on my face and I kept getting fucked slowly by Mr. B as I took Mr. W's soft cock in my mouth.

"You want my dick, girl?" Mr. W asked. I stayed quiet. "You want his dick?" Mr. W asked about Mr. B. I kept moaning softly not answering.

"You like this" he said and he pushed his cock that was now almost semi erect again in my face.

Between moans Mr. B said "Answer him baby. What do you want"

I knew what they wanted me to say, so I said it.

"I want your dick in my mouth" I looked at Mr. W. He knelt down again and his lips met mine. I tried to back up, pushing Mr. Bs cock deeper into me, my mouth opened into a moan but Mr. W used that to push his tongue into my mouth. He kissed me, his tongue exploring mine, his dry thin lips wrapped around mine and he rocked in motion with me while Mr. B fucked me.

Mr. B must have really wanted to see that, as he began to pull me onto his cock harder.. and within moments he pulled his cock out of my ass and that was when I realized he had been wearing a condom. He quickly pulled it off and he began jacking his cock.

"You want this?" Mr. B said as he stroked fast.

"Cum for me" I said and turned and met his gaze. He began to cum, aimed directly at my hole and I felt him shoot load after load into and into my ass. I pushed back without thinking, trying to take it back inside me, but I pushed me away and I felt the last few drops of cum on my ass before he rubbed his cock on it.

I didn't cum, but the thong was drenched in precum and I was still very horny. They told me I could go clean up and walking felt weird. I cleaned up and we talked a bit. Mr. B took a shower and Mr. W and I fulfilled the "contract" and I watched him delete the picture from his flip phone.

I changed back into my clothes, and we sat and talked a bit, Mr. B, Mr W and I. They asked if I liked it.. and I told them I did.

Mr. B asked if I still wanted his dick, and I told him I did. I ended up sucking Mr. B off once more before I left while Mr. W watched.

Mr. W told me that the reason he deleted the picture is because he knew I'd be back. He saw how much I liked it, and knew that I would come back. I left.. thinking that I might come back. Had it not been for the pain I experienced days afterwards and when I replayed Mr. W kissing me and how gross I felt, I might have.

I never did end up going back. That was my last experience with men.