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I've been struggling with how to write this next part because it is a progression of increasingly bareback sex, but all with random partners I met on the a4a, grindr and CL.  I am going to combine them into two sections, before Michael and after Michael, my next boyfriend.  This is only going to be a portion of the dozens of guys I actually hooked up with online over the years, but a good snapshot at how I was totally giving in to bareback sex.

 

At this point in my story, I was 26-27 and I had been trying to use condoms regularly and failing for years.  You've read how the need for bare cock and cum was increasing.  Ever since John said I was too slutty to date, I was more and more berating myself and saying that I needed to be a "good boy" or I wouldn't find a boyfriend who'd want to be with me if I was too slutty.  Besides the guys I met at John's party, I wasn't fucking anyone.  I'd meet guys at bars and parties and go home with them and mostly just do mutual oral and play around a lot.  I had fun, but not getting fucked was starting to cause and urge.

 

I was online one night chatting with a few guys.  I rarely met guys online because I was afraid I'd meet a stalker or a killer or something.  It was much safer to meet them in public right?  LOL.  

 

One night I was really horny and it was getting late and I was edging, watching porn, and chatting.  I was chatting with this one dude who was kinda attractive, shorter than me, blonde, but disproportionately large eyes which kept him from being hot.  He had an average cock (had unlocked that pic), liked getting his ass eaten, loved to give head, and was a total top.  He lived a bit away from me, but I was really horny.  He lived closer to downtown than me in a highrise building.  I really wanted to have sex, but parking was going to be a bitch.  He said he had a garage, but didn't want to give me a "guest passes" because he could only buy a limited number each month.

 

My cock was rock hard because I'd been edging and I couldn't believe I say it; but I said, "If I let you fuck me bareback will you give me a parking pass."  Of course his answer was yes.  I was in flip flops, running shorts (no underwear) and a tank top and there in less than 10 minutes.  He grabbed my semi hard cock as soon as I walked in the door and we started making out.  In less than a minute, I was sitting on his couch, naked, with him sucking my cock.  Online had never been my thing, but this was hot.  After a while, he said lets go to my bedroom.  He got naked, we made out some and he told me to eat his ass.  I did.  He had a nice smooth ass and it made me wonder if he really was a "total top."  I ate him for about 10 minutes and his cock was so hard he said he had to fuck me or he'd cum.  I bent over his bed and said, "Fuck it's going to be so hot to bareback your hot ass."  He asked one last time if it was ok and I said fuck yes.  He then lubed my ass and his cock up and slid inside my ass.  It hurt at first, but like I said he had an average cock so the pain was only there for a few seconds.  He fucked me really well and jerked my cock.  He wasn't going to last long, so I asked him to put lube on my cock so we could cum together.  Within a few minutes he said, I'm going to cum and shot his load in my ass.  I came a just after and he caught my cum and licked it off his hand.  I used the bathroom to get cleaned up, put on my clothes, got the parking pass, and left.  The parking attendants must've known what I'd just done, but I didn't care.

 

Less than a week later, I was online again and chatting.  There was a hot marine a few miles away in an apartment building.  He was normally very much a bottom and was a bit older than me - mid to late 30s.  We'd been chatting some and he eventually asked about fucking bareback.  I said I had fucked bareback and he said, "If you let me bareback you I'll fuck you."  I said yes and was at his house fast in what was now becoming my online hookup outfit, tank top, running shorts (no underwear), and flip flops.  I got there and his roommate let me in the outer door as she was leaving.  He was talking on the phone when I got upstairs.  He motioned for me to sit on the couch and kept talking.  He was talking to someone about tests and studying, track team, stuff like that.  I was like, "What the fuck is all this."  He grabs me a beer and rubs my cock as he is talking.  He sits next to me on the couch and I'm not kidding, he says to the guy on the phone (his son), "Make sure you use a condom."  I was floored and almost burst out laughing.  Here was this regular marine bottom dude who was only willing to fuck me if I let him do it bareback telling his kid about using condoms.  He got off the phone and we made out and he got me naked.  He took off his shirt and we went into his room.  He had floor length mirror closet doors.  I got to watch myself as this dude dropped his shorts, lubed his cock, slid it in my ass and fucked me until he came in my ass.  I fucking loved watching myself get fucked in the mirror.  We cleaned up after he sucked me off and swallowed my load and said maybe next time we can flip.  I was like sure, but that never happened.  LOL.

 

Another night, it was late, like 2 am and I wasn't drunk but had been drinking.  I was chatting with these two Latino guys who both had 8.5"cocks.  They were not that attractive, but their cocks were amazing.  The guys lived a while away and I decided fuck it, I'll drive.  They were very clear about wanting to fuck bareback.  I was like, sure.  At this point I was almost always getting fucked bareback by my online hookups.  I got to their apartment in my hookup outfit - tank top, shorts (no underwear) and flip flops.  We got right down to it because the one guy didn't speak English that well and the other guy had to translate.  I slipped out of my clothes and got on their bed.  The thinner guy got behind me and started eating my ass right away.  The chubbier guy got on the bed and stuck his cock in my face.  I sucked it.  After a few minutes, the thinner guy grabbed a basket of lube and condoms.  I realized at this point that the chubbier guy had been the only one chatting with me and the thinner guy didn't know I'd agreed to get fucked bareback.  He took out a condom and I said, "You don't need that."  The guy asked if I was sure and I said yes.  So he lubed up and fucked me.  His cock was a lot bigger than anything I'd taken recently so it took a minute for me to adjust.  He slid in and out of my ass so well, I was moaning around the cock I was sucking.  He starting fucking me harder and I was in fucking heaven.  I could see myself spitroasted in their mirror above the dresser and I was so hard.  When I'd come up for air, I'd look over at myself being a total slut and was loving it.  One of these times, the thinner guy abruptly stopped fucking me and I realized my ass warm.  He'd shot in my ass without telling me.  He pulled out, went to the bathroom and I heard the shower start.  The chubbier guy slid down the bed and I'd been sucking his cock so it was wet.  I sat on his fat cock and slid right down thanks to my spit and the cum already in my ass.  I rode him for a few minutes and he said get on all fours so I can cum.  I got on all fours and the chubbier guy starting ramming my ass. I was so open my this point that I just put my head down on the bed and let him rail me.  He roared as he came up my ass.  He had been jerking my cock but the pounding my ass was taking got all my attention.  As he came I felt so awesome and he jerked my cock one more time and I shot all over their bed.  A few minutes later, I was out of their place and driving back to my apartment.  That fuck was awesome and I could feel their cum running out of my ass as I drove.  So hot.

 

More to come.....

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Posted (edited)

Telling the story of Michael is hard.  He loved me and wanted to move in together and build our lives together.  Unfortunately for Michael, my need for other cocks and more sex drove me to break up with him.  This is the story of Michael.

 

My friend Tim, a guy I had met through a friend of a friend, asked me to go to a party with him.  Tim is gorgeous.  He is like most guy's wet dream, beautiful face, cut body, 6'3", maybe 200 lbs.  He's that guy.  I didn't know until I got there that this was one of his trick's parties.  He said something like, "This place is nice but it's noisy in the morning because it's close to the street."  I was like, "oh fuck, I'm here as your shield against the trick and his friends and possibly doing something you don't want to do.  Thanks Tom."  We both laughed at the truth of it.  The host and his roommate were really hot though and in the end Tom allowed himself to be the host's arm candy for the night.  

 

As Tom disappeared into the crowd, I started talking to a group of guys near the bar.  One of them was Michael.  Michael and I were instantly attracted to one another.  He had a high school soccer player build, no longer tight but all the right proportions, brown hair and eyes.  He was so nice.  Within a few hours, his hand was on my ass and we were kissing at the party.  I told him I was a bottom and he said he was a top.  We stayed out partying until 4am going to bars, dancing, making out, etc.  Eventually we went to his place.

 

Michael was so sweet and aggressive at the same time.  I was on my knees sucking his really nice 7" thick cock as soon as we were inside his door.  I got him hard and wet and he dragged me to my feet and down the hall to his bedroom.  I had my shoes and pants off before we got into the room.  I wanted to feel him inside me really badly, but I didn't want him to think I was a total whore, so I continued to suck his cock.  As got naked and I ate his ass.  He then sucked my cock and ate my ass.  I was now face down on his bed.  He was rubbing his cock on my ass crack as we made out.  Every few strokes, I'd widen my legs and his cock would run more over my hole.  I just wanted him inside me.  I said, "Put some lube on my ass so you can slide easier."  He did and put some lube on his cock too.  He teased my hole a lot with his cock and I kept telling him to fuck me.  Eventually after teasing me forever, he slid his bare cock in my ass.  After he bottomed out inside me, he asked if I was sure I wanted to get fucked without a condom and I said "yes, you feel so good in my ass."  Now he started just fucking away at my hole.  He had me close the whole time because my cock was rubbing on the sheets as he was fucking my ass.  I said I was about to cum and he sped up his fucking.  I came and he stopped for a sec and then started fucking me again.  He asked if he should pull out.  I said cum inside me.  He roared as he came in my ass.  It was so awesome to have him fill me up and how he tensed up and then held me.

 

I had him fuck my ass 2 more times that night and once more in the morning.  He asked a few more times if I wanted him to use a condom.  I kept saying no.  He bred me four times that night.  We went and had breakfast in the morning and his cum was leaking from my ass as we ate pancakes.  

 

By the next Monday, I was already texting him begging him to fuck me again.  We texted a bunch of dirty talk and he made me text over and over again that I wanted his bare cock and his load.  We fucked every night that week.  Even nights when we had other plans, we met afterward and fucked.  I was like a cum crazed whore.  

 

Within a few months, we were also talking more and dating like a regular couple.  Sex was hot, but not as frequent and I was still on my knees every chance I'd get to suck him so he'd get hard and want to fuck me.  One weekend a friend of his, Jakob, came to town and we all went out drinking and dancing for a few nights.  On the Saturday night, Jakob admitted he'd heard us fucking the night before and was surprised I was the bottom.  We laughed and I said, "I think I've fucked him maybe 5 times.  I always want his cock in me."  We were really drunk when we got back to Michael's apartment that night.  Michael and I fucked twice that night and we didn't try to keep quiet.  I woke up earlier than Michael and was pretty hungover.  I went to get a glass of water and see if Jakob was ok.  I figured I'd put a glass of water near him for when he woke up - something Michael and I did for each other too.  

 

As I brought the water over, I stubbed my toe on the coffee table and quietly yelped.  His friend woke up and asked if I was ok.  I said sure and gave him his water.  He asked if we had any advil and I went to the bathroom to get it and put Michael's water on the nightstand and went back out to the living room.  I closed the door to the bedroom so we wouldn't wake Michael if we talked or made breakfast or something.  I brought Jakob the advil and took some myself and we sat on the couch.  Jakob got up to use the bathroom and I finally saw his body - he had a rocking ass and nice abs.  He was only wearing small briefs.  I stared.  He smiled back at me.  

 

When he came out of the bathroom, he had grabbed the bottle of lube we kept in there and said, "We don't have a lot of time and I want to fuck you."  I don't know why, but I was bent over the couch with my ass out two seconds later.  He lubed his cock and slid inside me.  I guess it was really long when hard because when he bottomed out inside me, he hit a place Michael hadn't ever hit.  I was stunned.  His cock was thinner than Michael's but was really far inside me.  He said, "I hear you begging for Michael's bare cock and his loads.  Let's not pretend you won't take my load."  He started fucking me with short strokes and kept hitting that spot in my ass.  I was loving it.  He started fucking me harder and I was trying not to make any noise, as was Jakob.  He started stroking my cock and fucking me faster.  He came inside me quietly, flipped me over and sucked the load out of my cock.  I was spent.  

 

Jakob put his underwear back on and then went to take a shower.  I went back to bed with Michael.  When I got in bed, he reached over for me and I told him Jakob was awake and taking a shower.  Michael said there was just enough time to fuck me again and I let him.  He didn't need any lube and said my ass was so wet.  I told him it was his cum and lube from the night before (like 5 hours ago).  He chuckled and said I was really a great bottom bitch.  He slammed his cock into me over and over and I was moaning and grunting.  Michael came inside me and we collapsed.  He kissed me and went to get me off and I said, "Don't worry about it.  I am happy not cumming right now."

 

I felt guilty for weeks after that.  I'd never cheated on one of my boyfriends before.  It was breaking my heart every time he said he loved me and every sweet thing he did for me.  I was also getting hard regularly thinking about that spot Jakob hit inside my ass.  I knew Michael would never get in that far.  I'd think about Jakob's cock inside me as Michael fucked me.  I was really torn.  I knew Michael and I could never have an open relationship.  He and I had done threesomes, but they were awkward for us.  

 

Michael and I eventually lasted just about a year.  I never told him about Jakob, but I couldn't forget that I'd cheated and how fucking good Jakob's cock felt inside me.   I was getting distant and he knew something was up, so one day I told him I didn't think I was going to be as happy with him as he was with me.  I broke his heart when I broke up with him.   I felt terrible.  Within a year, I had gone from his cumdump the night we met; to begging for his cock; to taking his cock every chance I got; to not being satisfied with his cock; and then not being satisfied with the relationship.  

 

I broke up with Michael because I wanted more and bigger cocks.  There was no other reason.  I gave up a great guy for more cock.  I didn't know what was happening to me.  A few years ago, I'd have been totally happy and in love with a guy like Michael.  He was my goal - stable, hot, good sex, funny, smart, sweet; but it wasn't enough.  Jakob's longer cock had shattered that happiness for me.  It reminded me how great it was to get fucked by different cocks and used by different guys.  What was happening to me?!?

 

 

 

A quick note on Michael:  He is an amazing guy.  He got married a few years ago.  He and his husband, who I see out every once in a while, are really happy together.  They now have two kids and they are the family Michael wanted to have with me.  I'm glad he's happy.  I'll never forget that I broke his heart.

Edited by jbucktown
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Posted

After Michael, I moved further into the city - an up and coming neighborhood with yuppies east of me, hipsters north and south of me, and a gentrifying Latino community to my west.  I had a great apartment and I was a 20 minute walk and 6 minute train ride to work.  

 

I knew I needed to get a lot of sex after Michael.  I needed to get his crying face out of my system.  I thought if I could just get the "sex crazed" part of my 20s over, then I could settle down with the next guy.  Seems logical, right?  I also wanted to screen my guys and mostly meet them before we fucked.  I had made rules for myself:  

 

1.  No guys with bfs(unless a 3some) because I still felt bad about Michael.  

2.  Always use condoms with guys you meet just for sex.  

3.  Poz guys are ok, but we have to use condoms. 

 

The following chapters will show how those rules slowly got stripped away.

 

My Grindr, a4a, and manhunt accounts were always on and I was chatting online with a bunch of people. I met up with a lot of guys and usually kept to my rules in the first year or so.  

 

1.  No Boyfriends.  I met this guy on Craigslist.  He was a hot fireplug kind of guy and had a decent cock and was funny online and when we spoke on the phone.  It was really late when he was leaving work and I suggested we mess around the next day/night.  He said he really wanted to do it now.  So I cleaned out and he arrived at my place about 30-40 minutes later.  Turns out he has a socks and shoe fetish, so when we messed around he wanted me to wear my running shoes and then when we were going to fuck he wanted to sniff my socks as we fucked.  I was ok with the fetish.  It was harmless and he was nice.  

 

I slipped off my shorts, only in socks and runners now and he sat on my bed and took off everything but his socks and underwear.  We made out a lot and he sucked my cock and I took off his underwear and sucked his.  He had me sit on him and rub his cock on my ass crack and hole.  He flipped me on my back, grabbed the lube and slicked both our cocks.  He took off my runners and kept sliding his cock on my ass as we made out.  He asked if I had any fetishes and I was so turned on that I said, "I like it when guys cum in my ass."  He seemed startled but not for long as his bare cock was sliding in and out of my ass next.  I moaned.  He sniffed my socks and started fucking me harder.  After 5 minutes or so he said he was close.  I grabbed his fleshy ass and held him inside me and he came in my ass.  That made me cum right then.  

 

We did it one more time that night and he bred me then too.  After he left, we swapped texts about doing it again.  After a few aborted attempts at getting together again, he admitted he had a boyfriend of 10 years that he was cheating on and the boyfriend didn't know.  What's even worse is that I worked with his boyfriend.  He was senior to me at my law firm, but not in my section/interest area.  I was like...mother fucker, this is why no boyfriends.

 

That no boyfriends rule didn't last at all.  Cain and Abel entered my life.  They are an open couple that had just moved to town from Florida.  Cain was a solidly built, but gaining some weight/or losing it (depends on the month) guy with a great 6.5" thick cock.  Abel was a lean Latino nerdy type with a 7.5" uncut cock.  I hit each of them up - one on a4a and the other on manhunt.  I never knew they were a couple.  I met Abel for a martini at a local yuppie/hipster place and he was a great guy.  During drinks Abel said he and Cain were a couple and that they had an open relationship.  After Socks Dude, I wanted to meet them both together before I'd do anything with either one.  I explained my cheating past and said how it weighed on me.  Abel understood and called Cain, who had just gotten back from work, and they invited me over to their condo - about 1/2 mile from my place.  We hung out, Drank wine and they explained how and why they were open.  In their relationship, Abel was the top and Cain was the bottom; most of the time.  When they fooled around, they could switch that up and not let it interfere with their relationship.  They also said they always used condoms when they fucked other guys.  I was cool with all of it.  I stayed over that night and we had some awesome threesome sex and one-on-one sex while the other watched.  It was great.  And we played safe the whole time.

 

I met up with each of them separately for a while.  Always safe sex and I topped and bottomed with them.  They weren't my fuck buds really, since they had others and I was still dating around.  One night Cain was over at my place and we were talking.  He said I had gone out with a dude they knew - Jon - and that he told them I let him fuck me bareback.  I was a bit freaked out.  This is the kind of information I didn't want getting around because people would think I was a whore and no one would date me again.  I froze and didn't know what to say.  Cain said, "It's ok, but why didn't you tell me?"  I said, "I didn't want you to think I was a whore.  And we always use condoms so there is no way I was putting either of you at risk." My response had stumbled out so fast that he could tell I was freaked out.  He came over and kissed me and stood me up.  He stripped me and said, "Baby you are so fucking hot.  I don't think you did anything wrong. I think Jon was lucky to get to fuck you bareback."  I leaned over, opened his shorts, got on my knees and sucked his cock.  I wanted to make Cain happy and hopefully he wouldn't tell people about me barebacking with guys.  After a few minutes, we went to the bedroom where he bent me over the bed, reached over and grabbed the lube and a condom, lubed us both and slid his cock inside me bareback.  He had left the condom unopened.  He said, "You're beautiful and I want to be one of the guys who fucks you bare."  I pushed my ass back on him and started to fuck myself on his dick as he stood there.  He eventually flipped me on my back and had me jerk off as he fucked me.  After 10 minutes or so (not long for Cain), he asked me to cum because he wanted to unload inside me.  I stroked faster and faster and came and Cain loved the tightening of my ass when I came shot his load in my ass.  He said that was really hot.  But also said I couldn't tell Abel.

 

Cain was out of town for work and Abel and I grabbed a drink at the martini place (they are awesome martinis).  Abel and I went back to my place after because he said he wanted to fuck me.  I was always down to get his hot uncut 7.5" cock in my ass.  On our walk, Abel said the same thing Cain had about Jon fucking me bareback.  Abel was concerned for me.  I said I get tested, etc, etc.  He asked why I hadn't told them and I said it was because we always fuck with condoms so I didn't want them to judge me.  Abel pushed me against a tree and kissed me.  He said, "I won't judge you.  Cain is the condom Nazi in our couple."  I said, "You can fuck me bareback tonight if you want."  He said that's what he wanted tonight and every time we fuck after.  We got in my place and he fucked me bareback and came in me three times that night.  I was in cumslut heaven.  He said I shouldn't tell Cain.

 

A month or so later, I was at their place cooking with Abel and waiting for Cain to get home.  Cain called and said traffic is a bitch so Abel turned off the stove and said we have some time.  He told me to suck his cock and I did.  I loved his uncut 7.5" cock.  I sucked it and got it all wet and sloppy because I knew he wanted to breed me before Cain got home.  Abel turned me around and bent me over their kitchen island and slid his spit covered cock in my ass.  He fucked me fast and hard.  I knew I was getting the load soon and I was moaning and begging for him to cum in my ass.  Abel exploded inside me and I came on the floor and the island.  I was so turned on.  Then we heard Cain's voice, "So you've been barebacking our friend too?"  Cain came over and kissed Abel.  Abel said yes.  I slid to my knees and fished Cain's cock out of his pants and started to suck his thick 6.5" cock.  Abel said, "Was he as easy to get raw for you as it was for me?"  Cain said, "I bet he was."  I alternated between their cocks, wanted to keep them in a good mood (there were knives out since we'd been cooking and I was afraid this could go sideways fast.)  Abel's cock tasted like his cum mixed with my ass juice and Cain's was sweaty.  They both fucked me again that night; spitroasting me most of the time and saying what a good slut I was.  Whenever one of them was close, the other would make be beg for the load.  

 

We remained friends for a few years - they moved to California.  I was frequently getting fucked by them and they subtly passed me around to their friends.  They fucked around with all of their gay friends, so it was easy for me to hook up with those guys too.  A lot of those guys were in open and closed relationships.  I didn't care about their relationships anymore (that was their thing) and they all barebacked me.  I loved being slutty for that group of guys.  I see many of them around still and sometimes we still mess around, but I know they wouldn't spread rumors about me being a cumslut.  Their circle isn't like that.

 

More to come......

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By now, the "No guys with BFs rule" had been obliterated.  The next thing to go was condoms with hookups.  This shouldn't be a surprise to y'all seeing how the story has progressed to this point, but to me it was a change.  I had tried hard for years to be a "safe sex only" guy and I had been mildly successful given all the sex I was having; but I loved getting a load shot in my ass and it was becoming easier to just not ask for a condom.  I guess y'all would call me a "closet barebacker."  Not many of my friends knew unless they fucked me and I would still have condoms by my bed and still ask if a guy was "safe sex only" online.  

 

This began to change once I started to talk to a guy online who lived in the far suburbs.  His name is Chris.  I only ever met him twice.  Once on a date which didn't go well and once at a club when he was making out with a friend of mine.  Chris and I chatted online every time we'd be online.  I asked him about his dates/tricks and he'd ask me.  One night, as we were chatting he said something like, "and it was so sweet when I came in his ass" in reference to an 18 year old trick he'd just fucked the night before.  I was shocked, or pretended to be, that he'd barebacked with a trick.  He replied that he barebacked every guy he fucked.  He said he hadn't used a condom in years and every guy, even the "safe sex only" guys, let him bareback them.  I was immediately turned on and my dick started to get hard.  That night I hooked up with a guy and let him bareback me.  It was so awesome.

 

I told Chris what I had done and he asked how the sex had been and I told him it felt amazing.  He said that most bottoms want to get fucked bareback because it feels better but they won't ask for it raw because of diseases or fear that they'll be thought of as a slut.  I said that was how it was for me.  He told me to relax.  We chatted like my hesitation and he told me about his conquests for months.  I'd get hard as fucking imagining him fucking all those guys and how they all let him fuck them bareback.  

 

One Saturday morning, we were online early and he was telling me about his last hookup.  I was also chatting with another guy who wasn't far from me.  The guy I was chatting with was 22 and didn't have "safe sex only" in his profile.  Chris was turning me on with his hookup story and I asked the guy I was chatting with if he "liked to fuck safe or bb?"  It's a question I'd never asked before online, but I did because I really wanted to get fucked bareback that morning.  The guy I was chatting with said replied that he, "preferred to fuck bare" and I said I did too.  I gave him my address and he came over.  10 minutes later I was on my back and his bare cock was sliding in my ass.  He fucked me hard and quick and asked if I wanted his load.  I said yes and he shot it in my ass.  After he left, I messaged Chris about what I'd done.  He said I was a good slut.  I laughed.

 

As my online hookups progressed, I asked every guy the "safe or bb" question and most would say "bare" or "done both" or "depends."  If a guy said "safe," I almost never met up with him.  At this point, the condoms got put in a drawer and the lube stayed out.  If a top wanted a condom, I still had them but I had to get one for him out of my dresser.  

 

I think the final straw for me with barebacking tricks was a dude visiting from Minneapolis.  He was dirty hot and had a big dick.  We met on manhunt and his profile was clear, he liked fucking guys bareback.  We chatted for awhile and I was starting to think he was a "fake or flake" and then he said he wanted to come over.  I gave him my address, cleaned out, and was waiting wearing only my running shorts when he got there.  We chatted in my living room and he ran his hand up my running shorts and played with my asshole.  I moaned and kissed him hard.  He slipped my shorts off.  I was naked and opened his jeans and sucked his cock.  It had to be 8.5" cut.  I sucked his cock and played with his balls.  He took off his shirt and I helped him out of his pants while I was sucking his cock.  

 

We went to the bedroom and I laid back on my bed and he ate my ass.  He tongue fucked and finger fucked me for awhile.  Then, this guy who'd been really explicit about fucking me bareback, asked for a condom.  I was shocked.  I said, "You don't need to use one."   He said, "I know, but can I have one."  I got up and opened my drawer and handed him a condom.  I grabbed the lube and put some on my ass and cock.  He opened the condom as I was lubing his cock too.  When I leaned back he said, "I'll use this if you want me to."  I said, "You don't need to use a condom.  I want you to fuck me bareback."  He smiled at me and slid his bare cock in my ass.  I moaned into it and bit down on my lip as his cock pushed inside me.  Minneapolis Boy stretched me good and fucked the hell out of me.  He made me beg for his load in my ass.  I begged for it loudly.  He shot inside me and I shot on my stomach.

 

Minneapolis Boy and I fucked for his whole trip (3 days).  I even called in sick one day so we could fuck more.  He always made me ask for it bareback and he always made me beg for his load.  I did both every time.  He also told me I should throw away my condoms because I wasn't going to use them anymore.  I threw them away.  That was the end of my using condoms.  Now almost everyone was going to get my ass bareback.  

 

I had only one rule left, poz guys had to wear a condom.

 

More to come....

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Posted

I had always been freaked out about HIV and hence never really hooked up with POZ guys.  Over the years of fooling around with guys, dating, making friends, etc. I came to realize how bullshit that point of view was.  I fucked around with a few poz guys, but I always made them wrap it up.  I still hadn't barebacked with any poz guys that I knew of and I knew that not all the guys I had let bareback me could be neg, but it was still a choice I was making not to bareback with poz guys.

 

One night, I was online chatting with Chris and this Asian guy messaged me on manhunt.  His profile said poz and undetectable and he was hot to come over and suck my cock.  I put him off a few times.  Then Chris was telling me about the threesome he'd had with this couple and I was rock hard.  The Asian guy tried again and I gave him my address.  I was like, what did I just do?  But, I went in and took a shower so I'd be all clean and I cleaned out just in case something happened, but I doubted it would go that far.  As you know by now, I had no condoms in the apartment and that was another reason I thought we wouldn't fuck.  He was poz and I don't let poz guys fuck me bareback.

 

After I got out of the shower and changed into my running shorts and a tank top, he was at my door.  I let him in and he was aggressively kissing me right away and telling me how hot I was.  He grabbed my ass and slid his hand down my shorts and grabbed it.  He said, "Your profile says you're versatile, but with that ass I bet you're mostly a bottom."  I laughed and said yes and we went to the couch and made out.  He had me naked quick and was sucking my cock and fuck it felt good.  I was close and I think he could tell because he stopped and offered me his cock to suck.  After a few minutes he said he was close, but said he wanted to eat my ass for a while.  

 

We went to my bedroom and he ate my ass as I sucked his cock.  He fingered me too.  He also sucked my dick.  I was really horny.  I asked if he wanted to rub his cock on my ass.  He said sure and I laid on my stomach and handed him some lube to put on my ass.  He squirted some on my ass and fingered it into me.  I spread my legs as he fingered me.  Once he had three fingers in my ass I was moaning like a bitch.  That's when he started rubbing his cock on my ass and kissing my neck.  He said, "Don't worry. I won't fuck you.  I'm poz and you're not."  I moaned and kissed him as he continued to rub his cock over my hole.  I started to push my ass back some and he put his legs in between mine and spread my legs wider.  

 

Involuntarily, I pushed back as he was rubbing his cock head over my hole and his cock slipped inside me.  He pulled out and said he was sorry.  I said, "Don't be sorry your cock feels good."  He asked if he could fuck me and I said yes.  I could tell he was thinking about asking for a condom, so I reached back and lined his bare poz cock up against my hole and pushed back.  He moaned and said I was a hot white slut.  He fucked me for a while and then pulled out and came on my ass.  He said, "Fucking your white slutty ass bareback was really hot.  I told you I'm a responsible guy which is why I pulled out."  I said, "Thank you.  Your bare cock felt good in my ass."  We kissed, we exchanged numbers and he got dressed and left.

 

About two weeks later, he texted me and asked if I wanted to get my cock sucked.  I said yes.  He came over and this time we never made it to the bedroom.  He fucked me on the couch before he pulled out and came on my chest.  He sucked me off, got dressed and left.  He texted often after that calling me a white slut.  I loved that he called me that because it was true.  He came over and fucked me a few times after that and always pulled out and came on my ass or chest.  One time I swallowed his load.  That was really hot.

 

He wasn't really a fuck buddy in my mind, just a sexy guy who fucked me when he wanted.  He hit me up one day when it was really fucking hot out.  I was sweating just sitting in my apartment and he asked if he could come over because he was shopping down the street.  I said sure and got ready as quick as I could, but I was still in the shower when he got there.  I answered the door in a towel and we got in the shower together.  He sucked me off in the shower and swallowed my load.  Afterward, I was kinda sad he hadn't fucked me, but we sat on the couch and watched tv.  I was in my favorite shorts and he was in his boxer briefs.  We were both sweating in less than 15 minutes.  He leaned over and kissed me and told me to suck his cock.  I leaned over and sucked his cock and got him hard and wet.  I knew he was going to fuck me this time.  He pushed me back on the couch, pulled off my shorts and shoved his wet cock in my ass.  I yelped and he waited for me to adjust as he called me his pretty white slut.  I was so turned on by the name calling and his bare poz cock in my ass, that I was rock hard and ready to get fucked quickly.  I was stroking my cock and he started punch fucking my ass -pulling all the way out and pushing the whole length of his 6"cock back inside me.  Fuck it was hot and then he started fucking me faster.  Fuck it felt good.  He started jerking me off as he fucked me and i spread my legs wider and grabbed his ass.  I rubbed my finger on his asshole as he fucked me.  He was moaning and so was I, this was our hottest fuck yet.  I put my finger in his ass some and he started to buck back on it taking more of it in his ass.  I was finger fucking him as he fucked me (awkward position, but hot) and he said he was close.  I didn't let him pull out and he exploded inside my ass.  I had just taken my first load of poz cum knowingly.  I came all over the couch, my chest, him, everywhere.  He asked if I was ok with what happened and I said fuck yes.

 

Over the next few months, he fucked me a few more times and never pulled out again to cum.  He always shot his loads in my ass and by the end I was begging for his loads, just like with most of the other guys I was letting bareback my ass.  We faded after awhile, but it was always hot sex.

 

Now all my rules were gone.  I was letting every guy I met for sex bareback me.  I was loving it.

 

There are 2-3 more chapters of my transformation into a total cumdumpster.

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Posted

That last chapter was similar to me and my poz undetectable guy.  Didn't let him cum in me for a while then flipped a coin.  Third time flipping the coin it went his way and from then on he just fucked me and would cum in my ass.

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Guest iJoey
Posted

I have beat off to every and I mean EVERY story in this series.

Posted

This chapter is about my next boyfriend G.  He is another amazing guy and once again my love of cock ended the relationship.  Okay, to be fair, it was our mutual love of cock that ended the relationship.  There's other stuff that happened, other guys that fucked be bareback, a lot of random sex during this time period; but I think this was my next step in my transformation into a cumdump.   The timeline here gets muddy because I've already told stories that cross the timeline, so I hope you'll stay with me.  

 

As you know, I am an attorney.  I work for a decently large firm with an international client base.  This was about 3.5 years into working for the firm, so I was either on partner track or not by this point. I think I was because I was the 3rd attorney assigned to a case for a major client - partner, senior associate and me.  It involved a decent amount of travel for depositions, client statements, etc.  It was a total time suck.  I was easily working 100 hours a week in order to bill out at 75-80 hours a week which means both weekend days as well as long weekdays.  Granted, it's a U.S. law firm, not some jewel mine in West Africa - massages, free meals, gym, etc.  

 

It's at this time that I met G (manhunt, while working from home).  Oh my fucking lord, he is gorgeous.  People still refer to him as "that model you dated," even though he was a teacher.  I was totally amazed at how into me he was.  We met for drinks one night and drinks turned into dinner which turned into more drinks and dessert at another place and a hot makeout session in the car.  He wanted to fuck me that night, but I refused.  I was still thinking that guys don't want to date other guys who are too easy.  But, I wanted to fuck so badly.

 

That date turned into a second date and mind-blowing sex.  I would tell you all about how I seduced him into fucking me bareback or how he seduced me into it; but it's what we wanted from the first time our clothes came off.  We fucked 3-4 times every time we saw each other (no exaggeration).  He almost always fucked me and came inside me.  I was in total lust for G.  He did ask me to fuck him a few times and I did.  The first time he had the nerve to ask for a condom and I was like, "really?"  He relented of course because it was a stupid request since he'd cum in me at least 30 times by that point.

 

Then disaster struck.  He called me one day and said he thought he had gonorrhea and said we should both get tested.  I pretended to be surprised because I didn't want this to fuck things up with G.  My doctor had told me the day before and I was literally, at that moment, freaking out about how to tell him that he should get tested when he called me.  Later that week, we saw each other again and I thought he was going to break up with me.  Instead, he was all over me the moment I got to his apartment.  We fucked 3 times, as usual, in that 14-15 hour period.  The next morning after round 3 I said we needed to talk about sex and the diagnosis.  We hadn't talked about monogamy and I said it was time.  I said we didn't need to stop fucking other people, we just needed to stop fucking them bareback.  He agreed.  I was really happy.

 

And then disaster stuck again.  The senior associate on the case was diagnosed with a rare blood/bone marrow disease, which I still never understood because my work load immediately doubled if not tripled.  It was about time for summer interns to start, and I was worried about partner track, so I didn't immediate ask them to assign another senior associate to the case.  Instead, we got another me (associate) and then a summer intern.  But, my workload increased like crazy.  I was sleeping in a hotel down the street from the office a few days a week.  Travel also increased.

 

This meant I couldn't see G as much and fuck did I want to see him.  G and I started to see each other only on Fridays or Saturdays if we could.  He understood and supported the partner track goal and we also still fucked like rabbits.

 

One week we missed seeing each other and I had to travel the next week.  I made up my mind to have sex on the road that week because I was now getting it all the time and totally needed to get fucked or I'd go crazy.  I got online and found a dude to come fuck me.  He was attractive and I was ready for it.  I asked him to bring a condom and lube because I had made up my mind to do this while in the cab from the airport.  Instead of going to the drugstore I got on Grindr while I was in the cab and had made arrangements by the time I'd gotten to the hotel.  He got there and I had just finished showering.  His picture must've been a bit old because he had a bit of a belly, but I was horny and didn't care.  I wanted his cock inside me.

 

We got naked and he sucked my cock and ate my ass and I was eventually begging him to fuck me.  He lined his cock up to my hole and I was like, wait.....condom.  He said he forgot to bring one and I said, then no fucking.  I had promised.  It was my fucking idea.  I was not going to do this to G.  I said, "Let's just do other stuff."  He said sure and we sucked and he ate my ass some more and I ate his ass.  His cock was nice, like 7" and perfectly shaped.  He asked if I had any lube (forgot that too I guess).  Genius idea - hotel lotion.  I grabbed the lotion and hopped back into bed and we made out with me on my back legs spread and bent at the knee and him in between my legs and he put the lotion on both our cocks and we stroked and made out.  Eventually my legs were on his shoulders and he was rubbing his cock on my ass again.  I knew I was going to give up my ass this time if he pushed.  He did.  He slipped inside me this time and I didn't say stop.  In fact, I moaned like a whore because it felt so good.  He said he wouldn't last long and I said just fuck me.  He told me when he was getting close and I said nothing.  He came inside me and I blew all over myself.  I had just cheated again - this time after it was my idea and had done it bareback, also violating my idea.  The guy left and I felt kinda bad, but not too bad.  Each other night that week, another guy came over and fucked me.  Only one used a condom.  That's 4 guys and 3 loads in my ass.  I always told the guys safe sex only and then always gave in if they wanted it raw.

 

I got back to G that weekend and we fucked like bunnies again.  I said nothing to him, especially after I entered his bedroom and saw the lube/condoms/coke box out and open.  I knew he'd fucked around too that week, but he said "Don't worry babe.  I was safe." and he put the box away keeping the lube out.  That night/morning I had to ride his cock 5 times.  I was a cumslut for him and I loved it.

 

When I was out of town the next week, I took the "safe sex only" out of all my profiles.  I asked to get fucked bareback by every guy that hit me up and I got bred twice that week.  The next week was the same.  I even convinced a safe sex top to bareback me even though he was young and freaked out by the idea.  He still shot his load in my ass though.

 

This went on for a few months, but I didn't always have time to hookup so I wasn't always getting fucked on the road.  Every weekend I couldn't get home from the airport soon enough to see G.  I was falling for him and I knew it.  He never took no for an answer and neither did I when it came to sex.  If one of us wanted it, the other gave in no matter what was going on - the sushi delivery guy showing up while I was "load begging" was awesome.  LOL

 

One weekend, I was home but G was busy with his family.  I was really horny, so I hopped online just to chat and jerk off.  Instead I ended up talking to this average looking Latino guy who was into hot roleplaying.  He asked if I could do anything what would it be.  I said, "I want to pretend to be a safe sex only bottom.  I want the top to convince me to let him in bareback.  I want the top to make me admit I love bareback sex, that I only get fucked bareback, and then beg for his load in my ass."  He said that was really hot.  Then I said it - "Come over now and let's play."  

 

He came over and I was in my shorts and a tank.  He immediately felt me up, but I said "roleplay" and we did.  He talked to me about sex and slipped his fingers up my shorts.  I pulled out his cock and sucked it.  It was a nice fat cock.  I loved feeling his cock stretch my mouth.  I let him face fuck me for a while.  He got me up and told me to strip.  I did and he turned me around and rubbed his cock on my ass.  I bent over and spread my ass for him.  I asked if he brought condoms and he put them on the couch.  I loved feeling his cock on me.  He took me to the bedroom leaving the condoms on the couch.  He bent me over the bed and ate my ass.  He tongue fucked and fingered me.  He said I had a sweet ass and was going to love fucking me.  I asked if I had lube and I pointed to the dresser.  He lubed his fingers and pressed them inside my ass.  He lubed his cock and rubbed it on my ass.  He said how tight my ass felt.  

 

He pushed at my hole with his cock and slipped his head in my ass.  I moaned but said, "condom?"  He said, "Let me just feel your ass like this for a bit.  You moaned so it must feel good right?"  I said, "Yes, but we should play safe."  He just pushed in a bit more.  I moaned again and bit my lip.  I said, "We really should get the condoms."  He said, "But I'd have to leave your ass.  Let me just fuck you bareback for a while."  I said, "Ok.  As long as you promise to get a condom in a few minutes."  He slid his whole cock inside my ass and said how good I felt.  He started fucking me slowly and I was really loving his fat cock in my ass.  I started moaning a lot.  He said, "You like my dick in you huh?"  I agreed.  He fucked me some more and said, "Tell me how much you like it."  I told him it felt amazing.  He kept fucking me and said, "Feels good bareback doesn't it."  I said yes.  He said, "You don't want me to get a condom do you?"  I said, "Just keep fucking me."  He said, "You love getting fucked bareback don't you slut?"  I said "Yes, I loved your bare cock in me."  He then said, "You always bareback don't you?  You were just trying to play safe because you just met me right?"  He buried his cock in me as he said that.  I said, "Yes.  Guys always bareback me.  No one knows, but I love getting fucked bareback."  He asked me why I liked getting barebacked.  I said it feels a lot better.  He started fucking me harder.  He said, "What else?"  I was moaning and grabbing his fleshy ass.  He said it again, "What else?"  I said, "I like it when guys shoot their cum inside me."  I actually felt his cock get harder inside me as I said it.  He said, "Yeah you want my load slut?"  I begged him for it.  He slammed his cock in me and shot his load in my ass.  I was so turned on that I came less than a minute later jerking off.

 

It was so hot.  He got dressed and left.  I never saw him again.  But, I did see those condoms still unopened on the couch.  Fuck that was hot.  

 

It was a few weeks later that G and I broke up.  He wasn't ready for the relationship with me.  We'd been together for 6 months and the chemistry was awesome, but he could tell something was off.  I had cheated on him bareback at least 2 dozen times and didn't feel guilty at all.  Wow, I felt totally free from all that guilt I had from cheating on Michael.  It was really freeing.  I was sad that G and I broke up, but I was riding a cock in my hotel room down the street from work that night at 1am and begging for that guy's load, so I guess I didn't feel too bad.

 

P.S. - I made partner

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Posted

WOW.... What an awesome story, loved every second of it. Congratulations on making partner, and for being a cum slut bottom. There is nothing finer than the feeling of cum being shot deep into your ass. Hope to read more stories from you.

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