Author Notes: This story is a fictional depiction of past events I've experienced. Names changed where necessary and I've combined different events to create, hopefully, an entertaining story for you. The use of pronouns tends to fluctuate, and this is by design. One of the characters has been known to change his/her/their mind from time to time. No insensitivity intended.
I receive emails from a number of readers, and I thank you. Note, I try to respond as quickly as I can, but...life. Enjoy!
"Kid, you're drunk. I just can't." That's how it all started, damned near 20 years ago.
I guess I should go to the necessary backstory. Once upon a time, I was out of town on a business trip (as dubious as I'm sure that sounds) and stopped in Indiana to visit my baby cousin. I call her my baby cousin because she's almost 20 years younger then me. She was just turning 21 and I wanted to take her out as a birthday gift (and slip her a couple bucks, as most 'kids' usually need money). I was 'comfortably in my 30s' (creeping up on 40 if we're being honest) and doing alright for myself in life. I was divorced, had gone through multiple relationships and had in recent years been coming to terms with what a therapist once called my 'latent homosexual tendencies'. Latent hell...I liked ass as much as pussy. I had no qualms with a nice dick either (another development, in recent years, taught me that). So, I took my baby cousin out for lunch. We had a few drinks as well, and ran into a friend of hers. The friend mentioned a party and suggested she come along...and maybe bring the 'cutie' with her. The 'cutie' being me. We both laughed at this and explained our family relationship, and even though it was Indiana, we weren't about to cross that particular line.
I don't know how but my baby cuzz talked me into going to the party. I've never been big on parties, but I figured what the hell. If nothing else, I could keep an eye on my baby cousin. She always had a wild streak and I admittedly worried about her fairly often. So off we went.
Not knowing anyone there except my cousin made this an even more awkward situation than most parties. I wouldn't say I'm an introvert but it takes me a while to warm up to people, and vice versa. Baby cuzz seemed to know almost everyone there, so she was introducing me around. At one point, a very attractive yet obviously tipsy young gal came up to my cousin to inquire who I was. This gal was maybe 5'8, caramel complexion, long wild frizzy hair, and just damned good looking. She couldn't have been more than 20. Baby cuzz introduced her as Desiree and then found an excuse to leave us alone. I know...this already sounds like a tired fiction plot but trust me it gets better.
"Well, I guess you're stuck talking to the old guy now, eh?", I quipped to Desiree.
"You're not old!", she laughed. She guessed I was maybe 28 I guessed maybe she'd had too much to drink. We managed to have a nice little conversation. I couldn't help but notice she was sexy AF, especially in those skin tight jeans. I kept telling myself she was too young. She must've been a mind-reader. She kept insisting she preferred older guys like me. Unless I could convince myself to not be a dick and fuck my baby cousin's friend, this was gonna be a long night. I slowed my drinking way down. Desiree did not. She was clearly feeling no pain, and growing bolder with each sip. If I was sitting, she was damned near on my lap. If I was standing, she was putting her arms around me.
My baby cuzz came over at one point and noted how well we were getting along. She said we looked 'really cute' together, chuckled a bit and then disappeared back to the party with her friends. Desiree kept reiterating that we looked cute together, and how it must be a sign that we should be together. "Oh no", I thought to myself. A hippie type. Just what I didn't need. She'd be trying to align our chakras or something before long. Instead, she opted for a different plan. She put her arms around my neck, pulled me close and kissed me. I won't lie. I kissed back. I also noticed something, but as the thought was entering my head, I was momentarily distracted by some minor whoops of approval from the other partygoers (damn this felt like high school bullshit). Baby cuzz came up to say that there was something she should probably tell me, but too late, I was thinking with the wrong head by now. Desiree was making it clear that all systems were go and who was I to say no?
We snuck off to another room in the house where we could have some quiet alone time. The kisses were as furious and passionate as any 2 lovers. She would whisper in my ear things like "I'm so her type of guy'. She was thinner than I usually like but damn she looked good, smelled good, and her kisses tasted good. I kept noticing a little something, but she kept fondling my cock so any serious critical thinking was destroyed by that. She went and grabbed us more drinks and we sat and talked, kissed, and groped each other a while longer. She was really noticeably drunk by this point, and I was feeling uneasy about possibly fucking a drunk gal who might not even be all of 20 yet. Possible legal ramifications aside, I just didn't want to be that guy. Knowing my luck, she'd get pregnant.
We were pretty comfortable on a couch, and she was resting her head on my chest. She started to fumble with my zipper and trying to undo my pants. She slid down while doing so, looking up into my eyes with the prettiest brown, very drunk eyes. "I want to suck your cock", she said so sweetly. As much as I wanted her to, I stopped her.
"Kid, you're drunk. I just can't."
She didn't seem terribly deterred. She kept rubbing my cock, looking up into my eyes, and telling me that I was sweet to be worried about her. I finally got her all the way back up on the couch and said, "Look, we should probably talk. I really think you're hot, but I'm 38 and you ain't even close. Plus, we've both been drinking. This probably isn't the best start. Besides, I'm leaving tomorrow and heading home." I really didn't see the point in dragging things out. But Desiree had other ideas. She stood up, and slowly undid her jeans...
"Do you want to suck MY cock?"
I can't even guess where she was hiding it, but she whipped out a surprisingly big dark dick. She looked at me, smiling, and stroking it. "Well, what do you think?"
Mild shock mixed with turned the fuck ON is what I thought. It also explained what I thought I was noticing. Just the tiniest bit of stubble while we kissed. Not like sandpaper or anything, but I noticed something for sure. I'm sure my jaw was slapping the floor and I know my eyes were glued on that beautiful cock. This must have the 'something' baby cuzz wanted to tell me.
Desiree moved closer to me, cock in hand, slowly stroking it as it got bigger and harder. "You want this? want to touch it?", she teased.
I won't lie. I reached out for it. I had it in my hand, all 8-9" of it. It was big, fat, hot, and hard. I think I started to stroke it a bit. Then I stopped myself.
"Babe, I would love to...but you're really pretty drunk. I don't want you waking up tomorrow regretting getting wild with the old guy." That was the best I could come up with.
She sat down next to me, face in her hands, and started to sob a little. "You don't like me. You just think I'm a freak, don't you?"
Instinct kicked in, I put my arm around her and pulled her close. "No, I don't think that at all. I just don't want to start something we can't finish." Little did I realize, we already had.
I offered to take her home. Even suggested we stop for a bite to eat and maybe some coffee on the way. She seemed surprised by this, but it felt like the right thing to do. I got up, and went to find my baby cousin to let her know her friend was pretty drunk and I was going to get her home. I asked if she wanted to come along, but she begged off. She could get a ride; no problem and she said she'd call my hotel the next morning to make sure I got back OK.
I went back to get Desiree. She was still mighty drunk, but she was at least smiling now. Wow, what a pretty smile too. "You really do like me, don't you?" she asked, a few more times than she probably would have if she'd been less inebriated. As I didn't know the area, I was going to have to rely on her for directions. We stopped at a Denny's, had a bite and some coffee. I asked her where she lived and what the best way there would be. A bit sheepishly, she told me she lived with her boyfriend. WTF? As we walked to the car, I was wondering just what the hell I got myself into. We sat and talked in the car a while. I explained that finding out she had a boyfriend left me feeling uneasy. That's just not who I am. She explained that he was a jerk, and wasn't very nice to her. Staying with him with a matter of convenience. I was finding out more than I ever wanted to know. To anyone else, these all would've been red flags, but she seemed otherwise honest and genuine, so I just had to trust her on this. On the way to her place, she started rubbing my thigh and crotch again. I had to ask her to knock it off a few times. She'd just chuckle and say "OK", then a minute later, there was the hand again. She told me it would be best to let her off a few houses up from her boyfriend's. I agreed it might not be the worst idea. Last thing I needed was to get into a fight in a town I don't know, with some guy I don't know, for almost fucking his girlfriend, boyfriend, whatever Desiree was to him, and risk running into Johnny Law.
I pulled over where she suggested, turned off the lights and the car and we just talked a while more. Truth be told, she was easy to talk to, even half drunk. She was also really easy on the eyes. She gave me her number and asked if we could keep in touch. She said she really liked me and apologized for how the evening got a little out of hand. I told her it was no problem, took her number, and asked if she wanted me to call her when I got to my hotel...just in case any bad shit happened. She suggested I text, which I was happy to do. She kissed me then got out of the car. As she was walking away, she stopped, turned, smiled, and blew me a kiss. My eyes were glues to her ass as she walked away. I drove back to my hotel with a raging hard on.
As promised, I texted her when I got to the hotel. She texted right back, saying the boyfriend yelled at her when she got home. He guessed she'd been out partying (a blind man could have seen that) and he accused her of fucking around behind his back. (Close but no cigar) She said she yelled back, they fought, and she was sitting outside. She wanted to wait to see if I'd text, because that way she could at least go to bed with a smile. Little smiley emoji :-) Yeah, I'm a sucker. That got me. I suggested she try to get some rest, try not to fight, and if things got out of hand to call me. What was I thinking? Oh yeah...still thinking with the wrong head.
I made myself a drink and had a cigarette, thinking I should probably jack off for a while because I still had a hard-on like a 14-year-old in maths class. (Am I the only one that happened to?) My phone bleeped. I had another text. It was Desiree. "do u rly think i'm hot?' Was she kidding??? I replied with a simple "YES :-)" Then the phone rang. It was Desiree.
"Hey baby, can I ask you a serious question?", she asked as soon as I answered. Her voice sounded lower and a bit more male now, but definitely her. "Sure, you can ask anything you'd like", being really the only answer I could give. "You didn't seem to mind me having a cock. Do you like t-girls?" she asked. I wasn't really sure what to say, and I wasn't really familiar with the term, so I asked for some clarity. "Girls like me. We look like girls, but we're really guys, we have dicks, and the same, I dunno, needs I guess" was her answer. I just chuckled a little, and reminded her that I had it in my hand, didn't I? I told her that it took everything in me not to take advantage of a drunk gal. She told me I was really sweet, and that I was also really her type of guy. She said she liked them older and chunky like me (ok, that stung a little, but facts are facts). I told her that under different circumstances, we'd probably see a lot of each other. I pointed out that we lived hundreds of miles from each other, and that I'm not big on long-distance romances. While she thought that was a shame, she said she understood. Then she asked the sweetest question: "Can we be friends? I could really use a friend who gets me."
How could I say no? Afterall, I've already said she was easy to talk to. She was fun, and damned pretty, if not a little different. She asked if I had an email address, which I gave her. I had just got a laptop, which I had with me, so I let her know she could email anytime she wanted. We chatted a bit more, then I heard what must've been the boyfriend in the background. He was yelling like a little bitch. He even sounded bitchy. Squeaky little voice and all. I asked if she needed any help, and she just laughed and told me she was ok. She'd handle it. IF she needed me, she'd call. So, with that, we said goodnight, I jacked off for a while and went to sleep.
I woke the next morning to a text suggesting I check my email. She had sent a few. The first was to thank me for being so sweet and for being accepting of her. The next had a couple attachments and read 'Since you seem interested' with a little ;-) emoji. I opened the attachments and they were nudes of her holding her fully engorged cock. Probably fair to say they caused the desired effect. I couldn't get the thought of that beautiful cock out of my head. I texted her back to thank her for the emails, and suggested that if she expected them to turn me on, she was correct. I closed with a ;-) (hey, this was almost 20 years ago) I then went to take a shower, and jack off again. Damn, I was just too turned on.
After my shower, I saw that I had a few more texts. One from my baby cousin checking on me; the rest were from Desiree. The first one simply read "r u hard?", the others were along the same line. I texted back that I just got out of the shower, and apologized for not responding faster. My phone rang:
"You should have let me wash you" Desiree half-whispered over the phone. I joked that she was with me 'in spirit'. "Did you jack off thinking about me?" she whispered. I guessed the boyfriend was close by. I told her that I had a few times. She then whispered that she'd love to suck me dry. She quickly whispered she had to go, and she hung up.
I finished getting cleaned up, made sure my stuff was packed, had a cup of nasty hotel coffee, checked out and went to visit my cousins before my trip home. While there, I had a few texts from Desiree. I finally replied that I was visiting my cousins and then making the long drive home. She asked me to text her before I left, which I did.
I was sitting in the car, waiting to see if she'd text back. She called instead. She told me she really enjoyed meeting me, and wanted to see me again. Then she made me promise to text her when I got home. I told her it'd be late, but I'd definitely do that. On my drive home, she was filling my email inbox with more nudes and grainy little mpegs. After an almost 9 hour drive, I got home, unpacked and texted her that I was home. She texted back, asking if I'd checked my email yet? I replied that I would first thing in the morning. She replied that she hoped I liked them, and said goodnight.
I woke to a variety of pics and videos. Some nude, some almost nude, and some looking definitely more mannish. I wasn't phased or surprised by those. Desiree looked hot either way. One of the videos was just a little clip of her dancing and shaking her ass. The other was her, looking more manly, stroking that beautiful cock and fingering his ass. That one burned itself into my head for days. Any time I would let my mind wander, that's what came to mind. I probably watched that a hundred times that week. One email was an invitation to use Yahoo messenger. (told you this was years ago) It had a text box and a little video screen. I didn't have a webcam (yet) but I was curious to see how this worked. Desiree (now just shortened to Des) and I would chat on there a few times a day. Des usually messaged from the bathroom. Only place for privacy I guess. One day on messenger, she was clearly high. She was in the bathroom and being extra flirty. "Can I sho U something?" she messaged. Before I could even reply, Des had that big, beautiful cock in hand, stroking it for the webcam. I was mesmerized. "think u can take it" I feverishly replied that I'd love to try. Then phone emoji. My phone rang just as the screen went blank. "I want to cum all over your lips and lick it off", Des said, sounding manlier than ever. " Then I want you to fill my ass with cum" Fair to say Des was seeing me as more than a friend at this point. But, I agreed with everything. The only trick was finding a way to make it happen. Work had been slow, and money was tight. Sometimes we'd chat/text/email every day for weeks. Sometimes it would slow down. The boyfriend gave Des a black eye at one point. He'd found out about me and was pissed off. I offered to let Des come stay with me, but moving to a different state was a scary option.
We've stayed friends for years. Sometimes things cooled down a bit, but then they'd pick back up. I started dating a gal at one point, and Des came to visit. With my gal in the other room, Des (who was in full guy mode at this point) pulled his dick out and whispered, "touch it". I couldn't help myself. 6 hours later, I was on my knees with that cock down my throat.
Des went back to being fully male for a few years. Then tried being a 'tgirl' again. Then back. Confusing to say the least, but I like to think I understood. Being biracial, I guessed there were definitely some family issues about it. To me, either way, Des is fucking gorgeous. I think most people would agree.
Des was dating a woman for a while. Again, it didn't sound like a healthy relationship. I kept offering a place to relocate to, even if only temporarily. Des has yet to take me up on it.
In the past few years, our sexual interests in each other have kept up. Whether looking manly or more feminine, I think Des is hot. Des thinks I am too. Out of the blue, I'll get a text telling me "You should send me a pic of that ass. I miss seeing it." When I do, I usually get a reply like "Damn that's a big sexy ass! I want it!" Then Des will spend time detailing how Des wants me to eat his ass and fuck him. From a sexual perspective, we're probably a perfect match. We seem to dig the same stuff. And if nothing else, we're game to try new things.
A while back, Des messaged me that he was really getting into chubs in panties. He asked if I'd wear them for him and we could maybe jack off together. While not something I'd ever even considered, I do like it when Des is turned on by an idea. I had to take a business trip out near Indiana, so I asked if Des was up for a visit. I cleared a couple days, and got a room. While on the road, I stopped by an Adultmart to inquire about fishnet panties for someone about my size. The young lady at the store was happy to assist! After I checked in to my hotel room, I ran out, bought some wine and some fruit to munch on, and let Des know I was in town and to stop by my room after work. Des was thrilled at the chance to see me. Said he was going to stop home first to take a shower. I was already planning the same. I showered, cleaned myself inside and out, and put on a pair of lounging pants and a loose sweater (easier access to my nipples, which Des always enjoys playing with) and waited.
We hadn't seen each other in person for a couple of years. Life goes on, so they say. But we'd been in touch multiple times a day for a few months. Des was in for a surprise. I had the fishnet panties on under the lounging pants. When Des came to my room, looking hot as ever - hair tied back, a couple days of stubble, and incredibly tight jeans, we hugged, kissed, said hellos, and I poured us a drink. Des kept remarking how 'fucking good' I was looking. I said I might have a surprise for him (definitely 'him' at this point). I turned around, near the wall by the bed and asked how my 'big ass' looked in the lounging pants. Des sat on the edge of the bed and told me my ass would look better naked. I suggested he slowly take off my lounging pants, which he did.
"Aw damn, you sexy fucker!" is what he uttered when he saw the top of the panties. "You did this for me?" He slowly slid my pants down my legs. He slowly slid his hands back up my legs and began fondling and kissing my ass cheeks. He was making it clear that he wanted my ass and was going to have it. I felt his left thumb slide under the panties, and between my ass cheeks, squeezing and starting to spread my ass open. He stood up behind me, arms around me. How and when his pants came off, I'll never know. All I do know is his arms were around me, one hand fondling and squeezing my nipple, while he kissed my neck. I could feel his cock, still hanging, but getting hard and bouncing against my ass. He pushed me against the wall, and spread my legs with his foot, like a cop would. Still kissing my neck, one hand squeezing my chest, the other fondling my cock and balls, I felt his now hard cock between my legs. He was slowly starting to grind me.
He moaned in my ear "Baby, tell me you want my black cock...can you take it? I'm gonna make you feel so good taking this dick." "oh yes" was really all I could say, thinking how badly I wanted this. We'd come close so many times and here we finally were. Des spun me around and started kissing me hard and passionately, never once letting me out of his arms. He started to pull me down.
"Suck on my titties bitch" he practically ordered. I hadn't seen this side of Des before but damn, I liked it! Holding on to his beautiful ass with both hands, I began licking each nipple, getting them soaking wet with saliva. Des moaned so sweetly. I bit them, while squeezing his ass. I could feel his cock against me, and it was getting wet with precum. I licked my way down to his stomach, feeling his cock against my chest. I started to rub my fingers into his ass crack, lightly tickling his asshole. His moans were getting louder and I licked my way down to his cock. I was now on my knees and he was leaning against the bed as I began licking his big, black, veiny engorged cock. I pushed him back on the bed and took the head of his cock in my mouth, slowly licking and bobbing up and down on it. I started taking more and more into my mouth and towards my throat. It still wasn't even halfway in. I forced it down my throat and held it as long as I could before gagging. I went back up and back down until he grabbed the back of my head and stuffed his cock as far down my throat as I could take it. We did this a few times and then I popped back off, pushed his legs up and began to lick his ass (because I know how much he likes that). He was practically whimpering by now. I was tonguing his ass like a demon. He was moaning and stroking his cock as I did this.
Suddenly I stopped, looked him in the eye and joked "I thought you were gonna give me that dick" We both chuckled. "Oh, you think you're a bad bitch now?" he joked as he pulled me onto the bed with him. He sat up and put me across his lap. "Put that ass in the air Bad Bitch". As I did, he began to spank my fishnet-covered ass. We'd joked about this for years, but here we were doing it and it was really turning me the fuck ON! He giggled as my ass jiggled with each slap. I could feel my ass cheeks getting red and hot, but I didn't care. I was ready for anything!
He pushed me off him, stood up and told me to get on my knees. As I did this, he grabbed the lube off the nightstand. I heard him squirting it on his cock, and I went to remove the panties. "Oh no you don't! You're keeping those on you bad little bitch" he snickered. He then reached down and tore a hole in the back of the fishnet panties and started rubbing lube in between my ass cheeks and began fingering my ass with a lubed finger. He squeezed in more lube and added another finger, and another, and another. He was fucking me with his hand and it felt wonderful! He pulled me up to the bed and bent my top half onto the bed and put me in a doggy position. He started rubbing that huge cock against my ass. I'm sure I was moaning. He reached forward and pushed my chest to the bed.
"Raise that ass up for me baby" he said in the sweetest voice. When I did, I felt his cockhead probing my ass. Slowly, bit by bit, he worked it in. With little back and forth jabs, he worked more of it in. It felt like maybe half of him was in me, and he started long, slow strokes in and out of me. With each push forward, he'd go deeper.
"You like that baby? Does that dick feel good?" All I could do was moan agreement. "Arch your back, just a little...yeah, right there, that's it" he instructed. I swear, his cock was getting bigger inside of me. His long strokes were going deeper and deeper until I felt his body pushing into me. I could feel his balls hitting my ass. He kept pushing and grinding into me. My head was swimming!
"I'm gonna fuck that ass like a pussy!" he damned near shouted. He was thrusting in as far as he could, pulling out, and then thrusting all the way back in. He was fucking my brains out! I was jizzing onto myself and the bed. He kept fucking me faster, then slower, then with his cock as deep in me as he could get, he began faster and faster grinding thrusts. "I'm gonna cum!" and he pulled out and shot load after load all over my ass. Then he rubbed his still mostly hard cock in his own jizz and rubbed it all over my ass. Then he just laid on top of me, sweaty and spent, kissing my ear and telling me he loves me. Damn this felt good.
I got up to grab him a towel, and to clean myself off a bit. We laid down to just cuddle a bit. I got to be the big spoon. Soon, I was kissing his neck and shoulders and caressing his chest and stomach. My cock was right against his ass cheeks, so I started rubbing it up and down. This got Des moaning. I reached behind me for the lube, and lubed his ass, and kept rubbing my cock on his ass until it worked its way in. I moved the head in slowly. I let him get used to it for a bit. I'm no match for his cock size, but I've never had a complaint. He hadn't bottomed in a good while and he was tight. I worked my way in slowly, with slow little thrusts. Soon enough, I had him face down and I was fucking that beautiful ass. I made myself last as long as I could, then I shot my load deep inside of him. I slowly pulled out, and he just oozed my cum as we laid there for a while. Later, we showered together, played a little bit in the shower. He practically begged me to let him piss on my ass. I said yes, and he took a long hot piss on my now sore, hard-fucked ass. We might have to add that activity to future play dates.
Des is dating someone now. I'm married. We're still friends, but ya never know what tomorrow may bring.