Safe Sex Boy Turns Cumdump

[jbucktown]

Moderator's Note: The first couple of pages of this story don't have chasing in them. It only starts near the end. 

I've been lurking on here for a while and decided to post about my experiences slowly progressing from a safe sex only guy to a bareback slut.  I don't know how many of these stories I'll post, but if y'all like them, I'll post more.

 

I grew up in the late 80s/early 90s in New York.  In my brain back then, everyone who was gay died.  I tried hard to hide my sexuality.  When I would lapse and mess around with a guy, it was only oral and making out.  I never swallowed cum and always felt guilty afterward.  Eventually Aaron, a neighbor boy, and I started trying to fuck.  It hurt and we stopped most times, until one night in a not yet developed part of his subdivision he fucked me.  It was safe that time and every time he fucked me after.  

 

I'd always feel guilty after Aaron and I messed around, but we always did it again until I graduated from high school.  After that, we only saw each other when I was home from college.  Aaron is another story.  

 

My freshman year, I didn't really fool around with guys much.  I joined a fraternity, dated girls, drank and partied.  In was my sophomore year when I met my first boyfriend.  He was a medical student, 4 years older than me, at 23.  He always topped me and he always used protection.  I was also not really satisfied with our sex, but I was in love.  That is, until we broke up about a year after we started dating.

 

It was my junior year and I moved out of the fraternity house spring semester because I was tired of having a roommate.  I moved in with a straight guy and finally had my own room.  I hooked up with a bunch of guys and was learning to top as well as bottom.  I was having a blast.  I was still all about using condoms every time I fucked back then.  I was very serious about only playing safe.

 

Then I turned 21 and my friends and I started going to the gay bars to dance and drink.  It's here that I should say I was 6'2", blonde, blue eyes, 185 lbs with a 30" waist and a 7.5"cut cock.  I became really popular at the bars, not that I thought anything of it.  I would hookup with guys and still always used protection, but the more I drank the more likely I was to get fucked that night by a guy I had just met - white, black, latino, asian, didn't matter as long as they were young and hot.

 

One night, I was dancing on the box in jeans and a pretty tight fraternity t-shirt and this guy got on the box with me and we started grinding.  We kissed and went to get a drink.  We ran into friends and I learned this guy's name was Matt.  We had a few drinks, danced some more, and I could feel his dick getting hard as he was grinding my ass.   He said let's have another drink and talk.  We went off and talked and drank some more and he turned out to be a really cool guy. Unfortunately, he wasn't a local.  He was in town for work and staying with a friend for the weekend.  After a while, he kissed me and his hand slipped into my pants and grabbed my ass.  We made out at the bar like that for a while and then he pushed me into a darker corner and slipped his hand down the back of my pants and underwear and rubbed my hole.  I moaned and I kissed him hard and asked if he wanted to get out of there.

 

We left and went back to his friend's place a few blocks away.  He had me naked as soon as we were in the door.  I didn't even know if his friend was home, but I was naked and sucking Matt's cock in the living room of this apartment.  He was hard and I was getting his cock wet as fuck.  I wanted to make him feel good more than anything in that moment.  He took his shirt off and then as he got the rest of his clothes off he told me to turn around.  I got on all 4s and he ate my ass.  No one had ever done that before.  I was in heaven.  I was moaning and pushing my ass back on Matt's tongue.  He ate my ass for about 10 minutes and then he turned me over and we made out and I could taste myself on him.  It was so hot.

 

I wrapped my legs around his waist and we must've made out for 20 minutes or more.  It felt like forever and I was so into it.  The whole time his cock was rubbing in my ass crack and poking at my hole.  I knew we should stop and get a condom but I was so turned on and I figured we wouldn't fuck yet.  His cock felt so good on my ass that a spread my legs more and just then his cock slipped in my ass about halfway.  I was shocked and so was he.  We hadn't used any lube and he wasn't trying to penetrate me yet, but there was his cock in my ass bareback.  It felt so good.  I grabbed his ass and as he looked into my eyes questioningly, I said, "Don't stop.  Fuck me."

 

He started to rock his bare cock in and out of my ass.  I loved it.  No cock had ever felt this good in my ass,  On the floor on this random guy's friend's apartment, I was getting barebacked and I loved it.  I thought about stopping but I didn't want to.  I knew it was dangerous, but it felt so great that I just kept kissing him and saying "Fuck Me."

 

It didn't take long before I felt him getting close to cumming.  He started tensing up and I slid my hands down his back and grabbed his ass hard.  He looked at me as said, "I'm going to cum in your ass."  I said, "Do it.  Cum in me." and I pulled him into me as he shot his cum in my ass.  I'd never felt anything like it.  It felt so good that I came right after he shot his load in me.  He said, "Wow that was so hot.' and he slipped his cock out of my ass.  

 

He said, let's take a shower and we did.  In the shower he said, "I never thought you'd take get fucked bareback.  You seem like such a good boy."  I told him that was my first time bareback and he got hard immediately.  He asked if I wanted his bare cock in me again.  I just leaned against the shower wall and spread my legs.  He lined up his cock and for the second time ever, I let a cock in me without a condom.  He fucked me there until the water got cold and then we went out to the couch in the living room.  He slid his bare cock in me again fucked me on the couch on the living room eight next to my jeans where I knew I had a condom in the pocket.  I didn't want the condom though.  I just was his bare cock.

 

I was on all 4s and he was behind me.  He was getting close again and I was jerking my cock.  It's then that he said, "Tell me you want my cum."  I heard a noise, but was so into getting fucked that I just said loudly, "Cum in my ass."  He blew his load into my ass.  I was so turned on that I was in a haze.  I had just let a dude cum in me again and I loved it.  After a few seconds, we looked up and there was his friend who had just seen me getting fucked and heard me begging for cum.  He smiled and said, "Glad you're having fun Matt."  I was so embarrassed.  Matt was too, but less so than me.  

 

Matt and I slept together that night for a bit, but I couldn't sleep knowing what I'd just done and been seen doing.  I left Matt my phone number and left for my own apartment.  I was really freaked out, but that night and for almost a month I jerked off remembering Matt fucking me bareback and cumming in my ass.  I told myself I wouldn't fuck again without condoms, but part of me knew that wasn't true.

[wroxguy]

More story please, I love it...

[BrisFuck]

Keep 'em cummin' !

[jbucktown]

I couldn't tell what I should do.  I knew I could never fuck bareback again.  It was dangerous.  It was wrong.  People would judge me and think I was a whore and I'd never get a boyfriend if people knew because they would talk about me barebacking with guys.  So, I was a "good boy."  I tried hard not to hook up because I was picky, but also because I didn't want people to think any of that stuff.  I didn't mess around with anyone for a few weeks.  I still went out with my friends and got drunk and danced, but I was a "good boy."

 

One night I was out dancing and I met this hot guy.  Shorter than me, tight body.  Probably 5'8" and just ripped - Ripped Boy.  I was into him and we danced and drank and he wanted to hook up, but his friend was from out of town and single and he didn't want to hook up if his friend didn't.  I thought, he is such a nice guy.  I said, "Give me a second."  I grabbed this cute guy and pulled him into our dancing group.  I kissed him and asked his name, turns out he's a Navy Boy.  I told him our dilemma and he agrees to go dance with the friend and they hit it off.  Next thing I know, Navy Boy is back over to me and says, "I just felt that guy's cock and it's huge.  I bottomed last night and I'm still sore.  I'm not sure I should go home with him."  I am so accommodating and sweet and really want to get fucked by the Ripped Boy that I say, "It's no big deal.  Let's all go to Ripped Boy's place and hang out and see what happens."  Navy Boy agrees.  As we leave the bar I see Navy Guy is really sexy and that Ripped Boy's friend is attractive but not in Navy Boy's league.  I was nervous that they wouldn't hook up and Ripped Boy and I would then not hook up.  LOL.  

 

We all pile in Ripped Boy's car and his friend and Navy Boy are in the backseat.  I see the friend open Navy Boy's zipper as they make out.  Ripped Boy stops to get gas, Navy Boy runs inside for cigarettes and the friend says we should get condoms.  Ripped Boy agrees and then Navy Boy comes back with some beer and cigarettes and Ripped Boy says let's get some booze too.  So we all get in the car and hit this late night store and I run in and get some vodka.  Back out and in the car.  Now the Navy Boy has his shirt off in the back seat and Ripped Boy says, "You got my friend a total hottie.  Thanks."

 

Off to the house.  We get inside and Ripped Boy and I go to the kitchen, make out, he plays with my ass as I make the drinks.  Spilling some when he plays with my crack through my jeans.  We get back to the living room and Navy Boy is in his briefs making out hard with the friend.  Ripped Boy says, "No fair.  You should get naked too."  He grabs at my jeans as I hand the guys their drinks and put ours down.  I let him undo my jeans and I am in my boxers and I take off my t shirt.  I straddle Ripped Boy's lap just like Navy Boy was to his friend and make out with him.  It's getting really hot and I am hard as fuck.  Navy Boy and I kiss some too.  Navy Boy asks loudly, "Hey, you're a bottom right?"  I said yes.  Ripped boy slips his hands into my boxers and rubs my asshole some.

 

Navy Boy has finished his drink and into the kitchen we go so I can make him another one.  He slips my boxers down and rubs his cock on my ass.  He says, "You have a hot ass.  Can I fuck you?"  I said, "Sure, but I'm with Ripped Boy tonight."  Navy Boy grabs some salad oil off the kitchen counter and rubs some on my crack and hole.  He fingers me and says, "Please."  At this point the other guys come in and the friend says, "I bet we all fuck College Boy (me) tonight."  Ripped Boy walks over to me and takes the salad oil and says "Does this feel good?"  I laughed and said, "Sorta."  He kisses me and lubes up Navy Boys cock with the salad oil and says, "Fuck College Boy."  I spread my legs and kiss Ripped Boy, not thinking of anything but how turned on I was.  Next thing I know, Navy Boy's cock is slipping inside me.  I moaned and then the friend kisses me and Navy Boy is resting his cock in my ass.  I'm making out with Ripped Boy and the friend as Navy Boy starts to go to town on my ass.  Navy Boy and the friend start kissing and the friend takes off his clothes and Ripped Boy bends me over more to suck his cock.  I'm sucking his cock and Ripped Boy says to his friend, "I told you we didn't need them."  I have no idea what they are talking about.  I'm sucking cock and getting fucked.  I'm in heaven.

 

After a few minutes, Navy Boy tightens up and says, "I'm gonna cum."  Now I realize, Navy Boy who got his ass wrecked last night by some random dude is in me bareback.  I can't do anything much because he started cumming in my ass as I am still sucking cock and realizing we never used a condom.  I take his load and then Navy Boy pulls out and he and the friend grab their drinks and head back to the living room.  Ripped Boy is fingering my ass now as we share a drink.  I am so shocked that I just let another random guy bareback me.  I turned to Ripped Boy and say, "OMG!  That was so slutty.  I didn't know we weren't using a condom."  Ripped Boy takes my hand and leads me to his bedroom.  He sits me on his bed and I can feel Navy Boy's cum in my ass.  He climbs on top of me and we are making out so hard.  My cock is so hard because I had a load in my ass and was with this hot guy.  He spreads my legs and says ur ass is still so slick from the oil and Navy Boy's cum.  Blushing I say, "I'm sorry about that.  I didn't know."  Ripped Boy turns me over and rubs his cock on my ass crack.  He says, "Do you need more lube?"  I said, "No.  I think I'm good."  He slicks his cock up with the oil on my ass and slides his bare cock in me.  I said, "Fuck that's hot."  He said, "My cock in you feels really good."  He fucked me good for about 10-15 minutes.  Then he said, "I'm going to cum in your ass."  I said, "Do it.  I want your load."  I took his load and he slipped out of my ass.  He slapped my ass and said, "You are a hot fuck."  Ripped Boy and I made out some more and fell asleep.  I woke up with him fucking me early in the morning.  After a while on my side, I turned on my back and spread my legs for him.  I noticed his friend watching us from the doorway and stroking his cock.  Ripped Boy came in my ass again and fell asleep.

 

I got up to go to the bathroom and I came out and saw the friend on the couch in the living room stroking his cock.  I asked where Navy Boy was and he said, "He went back home."  I said, "Navy Boy was hot."  He thanked me for hooking them up and said I was hot too.  I walked over to the couch as we talked.  He had a 9" cock.  I said, "You have a big cock man."  He said, "Too bad Navy Boy didn't want to get fucked.  You looked like you like getting fucked by Navy Boy and Ripped Boy."  I blushed and said, "I did."  I asked me if there was lube in the bathroom and I said yes and went to get it for him.  I came back and squirted some on his cock and rubbed it all over his cock.  He pulled me on top of him and we kissed and I straddled him.  He said, "You like cock don't you?  Why don't you sit on mine."  I got shy and said, "We don't have a condom."  He said, "You haven't used one yet tonight."  He was right.  I was a cum dump for two guys already that night.  I gave in and he pushed his cock against my hole as I leaned back down on it.

 

He said, "Ride my raw cock bitch."  I did.  I rode him and made out with him until he was close and he said, "Take my load slut."  I sat down on his cock and felt him explode in me.  He just kept coming.  I was so turned on I came on his chest.  He loved it.  I eased off him and cum for three different guys slipped out of my ass and down my thighs.  I was so turned on and so scared of what I had just done.  Not just one guy, I had let three different guys bareback my ass in one night and I had taken their cum.

 

I went back to bed with Ripped Boy and fell back asleep.  We got up and he drove me back to my apartment.  I found out on the ride that he had a boyfriend.  I was kind of shocked and said, "But you just fucked me bareback and came in my ass twice.  How can you have a boyfriend?"  He said that I was so hot he had to have me.  I blushed and we exchanged numbers and he said, "Can I see you again when my boyfriend is out of town?"  I said, "Yes."  I got out of the car and he called out, "College Boy, come back."  I walked back the few steps and he kissed me hard and asked if I'd let his friend fuck me too.  I said yes.  He said, "You're so hot," and he drove away.

 

I went upstairs to my apartment and said I swore I'd never see him again because he was a cheater.  I also swore that I'd be better about using condoms.  I had to be, right?  No guy wants to be boyfriends with a slut, right?  I said, never again to both barebacking and seeing Ripped Boy.  I did see Ripped Boy again a few times, but I made him wear condoms.  He said he understood.  We stopped fucking when his boyfriend figured out he was fucking me.  I might have kept my promise about making Ripped Boy use condoms, but I did get barebacked again.  But, that is another story.  

[Bttm2go]

I really like your hot stories. Please post more. Thanks!

[wetboy27]

Great stories.  I'd love to read more.  Thanks for posting

[jbucktown]

I really was a "good boy" for the rest of college.  I dated a few guys and slept around some, but I always used condoms.  Even when I was back home and hooked up with my neighbor, Aaron, a few times we always used condoms.  He was becoming a great top.  I guess he much have been fucking around a lot because he made me want it every time I saw him.

 

I went to law school after that and my whole first year was hellish with studying, etc.  After my first set of finals, I went out and partied hard for two days - even missed my plane home for Christmas.  LOL.  When I came back for second semester, I was back on track and starting to look for 1st year summer internships.  I was dating a dude at this point, but we never saw each other and weren't exclusive.  He asked to fuck me bareback a bunch of times, but I always played safe.  I honestly think he was into me, but I was too busy to spend much time with him and we broke it off.

 

Over the summer, I got a summer internship at a decent sized firm and was working long, but not crushing hours and I was able to go out with some friends I'd made by hooking up and a running club and at law school.  I think I also starting chatting on AOL with guys at this point, but I couldn't bring myself to just hook up with a guy I just met online.  One of those times online though, I met an awesome, funny, smart guy.  His name was Will.  We agreed to go running one weekend.  I met him and we ran.  He was cute, had a great body, was my height at 6'2", was thin with a six pack from running and I was betting a hot cock.  We laughed and talked as we ran.  We had a great time.  I agreed to meet him and his friends out later that night for a pre-party at his place and then go out to the clubs.

 

He called me later and asked if I wanted to get dinner too.  I was so excited and said yes.  We shared a small dinner and then went around the corner to his friend's place.  He and his boyfriend and a couple of other guys were there.  He chatted and drank beers and vodka - Will and I on vodka.  We stayed there for a while and then went out to the clubs.  I hadn't been to a few of them and we danced and had so much fun.  Will grinded on me some (not a great dancer for sure) and we made out a lot.  At about 2am we left the club and went back to Will's place.  We kinda talked about it and I had said yes to staying over earlier in the night.  He had also said he was versatile and I said I was too, but mostly a bottom.  He said, "You're ass is so hot.  I bet guys always want to fuck you.  I know I do."  And we laughed.

 

We got back to his place - a studio in the gay neighborhood - and we started to make out even before his door was opened.  We got inside and made out a ton.  The room was literally - a bed and a desk.  No chairs or sofa.  I did a little strip tease of him and slipped off my underwear showing him my ass.  He rubbed my ass and immediately started rimming me.  His tongue was so good in my ass.  I was so hot for Will.  I wanted him so bad.  I wanted him to be my boyfriend.  I wanted him to fuck me.  I wanted the night to never end.  Mostly, I wanted his tongue to stay in my ass forever.

 

After a few minutes, he asked me to suck his cock and he got naked.  I went to town on his hot cock.  It had to be 8 or 8.5" cut.  It was a perfect cock.  Not to thick, but just enough to totally stretch my mouth and kinda veiny.  I wanted him to like my blow job.  I wanted that so much that I was so good at sucking his cock that he was going crazy.  He said after a few minutes that he was going to cum.  I did something I'd never done before.  I didn't stop sucking him and let him cum in my mouth and I swallowed his load.  He said that was so hot and that he never cums from head, but I was too good.  He asked how he tasted and I said good.  He said something silly about making his cum sweeter by drinking orange juice and eating bananas so guys would like the taste.  We laughed and cuddled on his bed.

 

He played with my ass some more and he gave me a good blow job, but pulled off when he could tell I was getting closer.  He did this a few times, which was "edging" me and I didn't know that's what he was doing at the time.  I was so hard and he was getting hard again.  We made out so long that the sun was coming up.  I'm not sure when it happened, but we grabbed some lube and lubed up our cocks and he fingered my ass some with it.  We kept lubing our cocks to "edge" and make it hotter as we made out.  Eventually I was straddling him and he was rock hard.  He was lying flat on his back and his cock was rubbing against my ass as we made out.  I said, "Do you want to fuck me?"  He said yes and I grabbed the lube an rubbed it on his cock and my ass.  

 

He was looking up at me and I could tell he was about to tell me the condoms were in the drawer.  At that moment, I did the sluttiest thing I'd ever done.  I wanted Will to like me and want me so badly.  I wanted that cock.  I was so fucking turned on by him.  I just sat on his cock.  I winced at first, but I slipped his whole raw cock in my ass.  He moaned and I moaned and I adjusted to his size and started to ride him.  He started fucking up into me and say what a hot piece of ass I was.  I was loving it.  I had just put a bareback cock in my ass myself.  It's not that I wasn't thinking at the time, I was thinking.  I was thinking I wanted him to fuck me bareback.  I wanted to feel what I'd felt with those other random guys.  But, Will was special.  I had just met the man of my dreams and I wanted him to bareback me.  It was so fucking hot to have him inside me bareback.

 

I rode him and he bucked up into me.  After a while, he said he was getting close and I didn't stop riding him.  I wanted him to cum inside me.  I wanted Will's load.  He said it again and I just kept going.  I leaned down and kissed him as I still rode his bare cock.  He then grabbed my waist and grunted so loudly and I felt his warn cum shooting inside my ass.  I didn't stop riding him and I started jerking my cock until I came maybe a minute later.  We made out and talked about how hot that was.  He said it was the first time he'd ever topped bareback.  I asked if he liked it and he said fuck yes.  I said I liked it too.  He and I made out and fell asleep.  We woke up in the afternoon and took a shower.  We agreed to meet for dinner at his place and to watch Sex and the City.

 

I made sure to look really sexy when I went over to Will's later that night.  We ordered food and made out some.  I sucked his cock and swallowed his load again.  Just then, the delivery guy showed up.  I laughed so hard as he tried to get dressed and pay the dude.  It was so funny.  He put the food in his tiny kitchen, came back in and no joke, we got in a tickle fight.  Next thing I know my tight jeans were coming off and I had't worn underwear because I needed to do laundry.  He grabbed the lube that was still on the floor next to the bed from earlier and lubed up his cock and said, "Let's fuck."  This time it felt a bit odd that he didn't ask me about a condom because he seemed like it always used them.  But, all I wanted was his cock inside me and I spread my legs and he slid his cock in me slowly.  I was still in my tshirt and I pulled that off as he bottomed out his cock inside me.  He asked if I was ready, I said yes, fuck me.  And he started to slide in and out and then long dick me and then pulled out and popped back in a few times.  He slam fucked my ass for a while and I just started cumming as he fucked me.  He noticed and sped up some and didn't even ask or say anything but came inside me and collapsed on me.  We kissed.  

 

I had just taken a second load from Will.  I wanted all his loads.  I was falling for him hard.  He was my perfect guy.  We watched Sex in the City that night and fucked again.  I rode him again that night and let him cum inside me again.  

 

Will and I went out for a few really happy months.  I was always running over to his place to get his raw cock in me.  I topped him a few times, but he was almost always unloading in my ass.  I think I took 200 loads from him in the 6 months we dated.  (Ah, youth!)  Then, one day I found out he was also fucking around with his neighbor, a really bitchy asshole named Jimmy.  I was so mad because I had been let into the building by a person who'd seen me there a lot.  I went upstairs and realized that there were noises coming from his apartment.  He was moaning and saying "keep fucking me.  Don't stop."  Then I heard Jimmy clearly say, "Do you want my load?"  My Will, the guy I was falling in love with said, "Cum in my ass."  I waited for that to stop and I was devastated.  My guy was cheating on me.  I knocked on the door and Will answered and saw me.  He was so shocked and I started to cry.  Jimmy laughed at me and Will, thank god, threw him out.  

 

We argued and fought and I pushed him and cried a lot.  I couldn't believe my perfect man who I had chosen to take bareback one the first date and every fuck after and taken over 200 loads from was cheating on me.  He said he cared for me a lot, but we weren't monogamous and he didn't want to be.  I was so hurt.  After about an hour, he held me and kissed me and wiped my tears away.  I let him hold me and I leaned against him.  He kissed my head and I kissed his chest.  He was still only in his briefs.  He rubbed my back and I kissed his chest more.  

 

I knew what I was going to do.  I had to show him I was a better fuck than Jimmy.  I saw him getting hard and I slipped off the bed, took off my shirts, slipped his cock out of his briefs and started sucking his cock.  I gave him a great blow job.  We both had a ton of mixed emotions.  He couldn't concentrate on me giving him head, so he pulled me up and we kissed and made out and he took off my pants and boxers and gave me a blow job.  I moaned and let him work.  Then, I went down on my knees again off the bed with him on the edge of the bed and sucked him some more.  I could smell the cum in him and the sex he'd just had.  I saw the lube on the floor and opened it and spread it on my ass.  I turned around and lowered my ass onto his cheating bare cock and rode him.  After a while, he flipped my over and I was bent over the bed and he started fucking me hard.  He knew I liked him buried deep in me and doing short strokes to hit my prostate.  That's what he did.  Soon I was cumming.  He didn't stop like he usually did after I came.  Instead he kept fucking me which kind of hurt at first, but I got used to it.  Then he said, "Take my cum."  He grunted so load and I felt him unload in my ass.  I was so sad and so horny and exhausted. 

 

Will and I never made it past that last fuck.  We slept together that night but I couldn't sleep.  My ideal guy was cheating on me and my ass, even bareback, wasn't enough.  I was devastated.  I was a 6'2", blonde hair, blue eyed, really attractive guy with a toned body and a good career ahead of me that was letting a guy cum in my ass at least 5 times a week and he still didn't want me.  I didn't know what to do......(until next time.)

[cumslut23]

Hot! Such a free fall

[jbucktown]

We broke up just around Christmas.  Just in time for winter break and I headed home to see the family and some old friends.  I sent Aaron, neighbor that used to fuck me, and email saying I was coming home and he emailed back saying that he was going to Florida with his family.  I was bummed out about the whole break up.  It wasn't I great Christmas.  I was scheduled to leave my hometown just before New Years and go back to school and party before 2nd year, 2nd semester started - the semester you land that internship which gets you your job after graduation (supposedly, it did for me).  

 

One night I heard the my neighbor's dog barking and realized that either Aaron's family had left the dog at home (unlikely) or they were back.  I pulled on my coat and went outside and saw Aaron bringing in some bags.  I helped him and said, "I heard the dog.  What are you doing home."  There was some story.  Drama!  

 

His mom and dad were there and I said hey, Aaron, his dad and I grabbed some beers and they lit a fire in the family room and we all hung out for a bit.   We'd been friends since our mom's met at the bus stop going to work when we were five.  He and I played baseball, football, Nintendo, everything together until we had started messing around.  His parents went to bed to give us time to "catch up."  Aaron and I chatted about school and work, etc.  We switched to bourbon (love his family's bar) and after a bit he asked about Will because I hadn't mentioned him.  I told him what happened - the cheating and he saw how down I was.  He kissed me and said, "Will's stupid.  You're the hottest ass I ever had.  Too bad you don't live here."  We laughed. 

 

He started asking if I was still mostly a bottom and stuff like that.  He said guys can become more versatile in relationships and I agreed but said that hadn't happened with Will.  He asked if I had loved him and said I think I really had.  Probably still did.  We poured more booze and he told me about the guys he'd been "seeing."  Eventually we kissed again.  His bedroom was on the first floor so we just took our drinks and went to his room.  I knew what he wanted so I took off my shirt right away and kicked off my shoes.  We sat on his bed and kissed.

 

We leaned back on the bed and made out some, but we knew he was going to fuck me so it didn't take long for us to be naked.  I sucked his nice 6" cock, kinda thick, but nothing like Will's perfect cock that had filled my ass for six months.  Instead of fucking, I just continued to suck his cock until he said he was close.  I didn't stop sucking him and then I did something with Aaron that I'd never done in our 10 years of messing around.  He came in my mouth and I swallowed his load.  After his cum high ended he said, "That was so fucking hot.  Did you do that with Will?"  I said, "First Date."  He laughed and said, "You changed for the better."  We laughed hard and just hung out naked for a bit.  

 

I hadn't cum yet and Aaron asked if I wanted my ass eaten.  I said, "Fuck yeah" and I spread my legs and lifted them up.  He laughed and said turn over.  I did and got on all 4s and he started eating my ass.  He had never eaten my ass before I was loving it.  He asked in between licking my ass and pushing his tongue inside past my sphincter if I had had my ass eaten before.  We'd never talked about it, because we usually just fucked and did oral.  I told him I had and he asked if Will was the first.  I told him about Matt from that night in college (part 1).  He stopped eating my ass to listen and he grabbed some lube and fingered me while I told him about the whole thing.  I even told him that I'd let Matt bareback me.  He wasn't shocked or disappointed.  He said, "That's so hot."  He asked if Will barebacked me and I told him, "Every time.  Even the first time."  

 

I asked if he had barebacked guys since I knew he hadn't dated anyone seriously yet.  Aaron said, "Most guys like it bareback.  Just not everyone does it bareback."  I said, "You didn't answer my question."  He told me a few guys.  I said, "Hot."  He leaned in and kissed me.  We kissed for a while with 3 of his fingers in my ass.  He then asked if I let those guys cum in me.  I said, yes. He said, "Hot. Can I bareback you?"  I kissed him and said, "Yes."  He immediately pulled his fingers from my ass, lubed his cock and placed it on my asshole, He started pushing in and I guess I'd gotten easier for a 6" cock to slide in my ass after getting fuck by Will's 8" cock.  I moaned and let him slide all the way in.  He said, "Wow man that's the fastest I've even slid into your ass."  He just started sliding in and out of my ass.  I let him take over and kind of pound my ass for a while and said nothing.  I was moaning some, but really thinking about Will.  Aaron started to jerk me off as he fucked me.  My thoughts came right back to him and how good he was making me feel.

 

He asked if he could cum in my ass and he said, "I really want to breed you."  I agreed and said, "I wanted his load."  He came in my ass like a flood.  I was so turned on.  He stopped fucking me but didn't stop jerking me off.  I came like a minute later and we kissed.  He said, "You should've told me that story about you getting bred years ago.  it was so hot cumming in your ass."  We made out and I went home, but we fucked around for a few more days before I left to go back to school.  We never used condoms again.  Mostly because we only ever fucked during one other time period when he came to visit me at school.  After that he got a boyfriend and stayed monogamous.

 

After I got back to school, I started to think that barebacking wasn't so bad.  I just had to be careful about who I let bareback me.  I'd only do it with guys I was dating or knew really well.  I'd never let a trick/hookup/one night stand fuck me bareback again.

[Tommy Tank]

Very, very horny story - love it

[wetboy27]

So fucking hot!  I love reading your stories.  Thank you.

[jbucktown]

I was back at school and dated some and fucked some, but I was focused on graduating and getting a job.  I didn't meet the right guy, but I did have a lot of safe sex.  I also graduated and got the job I wanted.  About six months into working, I got sick and needed to stay home.  I had nothing to do but sleep and jerk off.  I chatted a lot with guys online and this one college kid, Adam, was so great.  He was tall, thin, toned and a total top.  He was attractive, but not gorgeous and had a great 7"cock.  He offered to come over and cook me dinner.  

 

After two days of being cooped up in the house, I agreed to let Adam come over.  He did.  He made me chicken and potatoes - the first real food I had in days and we hung out.  We sat on my couch and cuddled some and watched tv.  I'm not sure what we watched because he kissed me soon into it.  I held back because I was sick, he said, "Don't worry about it, you seem like your getting better already and if I get it then I'll be ok in a few days."  So, I'm on my back and he's pulling off my shirt and pajama pants (still in my small briefs). He made out like this on the couch, my legs bend at the knees and his body between them kissing me.  He still had his jeans on but I could feel that cock.

 

I had a coughing fit at one point and he asked if I wanted a massage.  Adam was taking a massage class and said he was good.  We went to my bedroom and I laid down on the bed.  He slipped off his jeans.  He was wearing boxers.  Adam asked if I had lotion and I did (not professional), but he said it was fine.  He started rubbing the lotion in and it felt great.  He actually focused on relaxing me and the massage.  His cock was semi hard, but not raging.  After about 30 minutes, we started making out again and he played with my ass and I played with his cock.  Adam said roll back over and I did.  I took my briefs off at this point.  He massaged my ass cheeks and hole for a few minutes and then slipped off his boxers.  He rubbed more lotion on my ass and let his cock ride in my crack as he kissed me and we made out from behind.

 

He asked if I wanted him to fuck me.  I said sure and pointed to the table where the lotion and condoms were.  The condoms were right there.  He grabbed some lotion and kept working it in my ass on and it.  It felt really good.  He started to poke his cock at my hole and I thought he was only playing seeing as he had to see the condoms.  He kissed me hard and the tip of his cock poked inside.  I wasn't prepared entirely and I yelped.  He calmed me down and eased his cock in me some more.  Once his cock was mostly in my ass, he kissed me again and I said, "Are you in me bareback?"  He said, "Yes.  Does it feel good?"  I said yes and he started fucking me.  The whole time we fucked, I was not really clearly thinking because I was on dayquil and other stuff.  I was thinking about how good it felt and his motions were fucking my cock into the bed and I was getting ready to cum.

 

He kept fucking me and I said I was going to cum and Adam said he was ready too.  SO, I came onto my sheets.  Then a few more strokes and Adam came in my ass.  He never asked, but just did it.  After we showered, I said, "Was that safe?  Are you negative" etc? I was worried because I had just let a hookup fuck me raw and cum in me.  I had promised myself that I wouldn't do that again and I just had.  But he was sweet and we said good night and he left.

 

He and I spoke a few times that week and I decided to go over to his place on the other side of town the next Wednesday to see him, have dinner, stay over, etc.  During the week I had asked him a few times about condom use and he promised to have some for when we fucked. I was freaked out a bit.

 

I got there and Adam's place was a total college kid apartment with two roommates, dirty, stuff everywhere, etc.   I was like, oh my, it's college days again.  No matter, I was 25 and he was 21.  The roommates weren't there when I got there.  We went out and grabbed groceries and wine.  Came back to his place and decided to fuck first and then cook.  So we went into his room and got naked, more foreplay this time of oral and rimming.  He then picked up a condom and said, "Do you want me to use this?"  I said, "No, you've already cum in me once.  It feels better without it anyway."  So he fucked me bareback and came inside me.  We showered.  He fucked me in the shower and came in me again.  Then we cooked dinner and hung out.  His roommates came home and we all hung out for a while.  That night he bred me two more times and made me ask for his load the last time.  I slept over and then drove home.  My neighbors, a cute couple, saw me arrive in the morning in the same clothes I wore the night before.  They smiled and said, hope he was fun.  We laughed.

 

I liked Adam, but we just fizzled out after that.  I had let him bareback me and taken 5 loads off him.  It was really hot when I told him I would go bareback while he was holding the condom.  It turned me on thinking about it.  I guess getting barebacked wasn't terrible.  I just couldn't do it with everybody and no one could know I got fucked bareback because they would judge me.  I started thinking, I hope these guys don't tell everyone that they fucked me raw.  It made me nervous.  But, if I could just not get barebacked that often, it would be ok.

[negbtm]

can't wait for more!

[joethomas]

Sounds like some really fun times. Makes for really hot stories!

[jbucktown]

After Adam, it was a while before I barebacked again.  I had sex with Aaron again over Christmas, but other than that I really wasn't messing around with guys much.  I was working really hard and my firm is the kind where I can work late (past 8pm) and they provide dinner and you get a car to take you home.  That seemed so much easier than any other way of working and I needed to keep my billing hours up.  Basically, this is why I wasn't fucking around much.  

 

One day, I went home at 8pm because I wanted to jack off and then work in my underwear with the tv on.  I would feel more relaxed.  I also popped on AOL and a4a, no grindr yet, and was chatting with guys while I worked.  Both my profiles were very clear, SAFE SEX ONLY.  I found this really great guy, John, and he was one of those guys that gets me to open up easily and he was also hot.  He was shorter than me, 5'11" and had a baseball player's build - big arms and shoulders and strong legs with a tapered waist and tight stomach (no abs showing like me, but I was just thinner).  We had a good time chatting while I worked.  I worked like this at night a few nights a week over a period of a few months and I'd regularly chat with John.

 

John was a great guy, living in the suburbs about an hour away, and I was never sure that I'd meet him.  I learned that he was kind of slutty, which I liked.  He dated a lot of guys, but was never finding someone he really wanted to date long term.  His parents and friends were cool with him being gay and he still lived at home, which was a nice suburban house with a hot tub and pool, nice backyard, deck.  I told him about Will and Aaron.  I told him that I was mostly a bottom, but was working a lot and not doing much with guys.  We talked about music, movies, etc. and had a really good time chatting.  It was easy.

 

One night we chatted about bareback and safe sex.  I admitted that I had fucked bareback with a few guys.  He responded by saying that my profile said safe sex only and I said, I really want to use condoms, but I can get carried away.  He said, he'd done it with and without condoms.  I asked how he made is decision about condom use and he said he could always tell when a bottom was slutty enough to fuck without condoms.  I asked how and he said sometimes by how they act or what they say, but usually how they act and what they say when they are naked.  He said the key was whether or not the bottom specifically mentioned a condom once they were about to fuck.  He asked how I decided and I told him it was usually spur of the moment and I didn't think about it.  But, I did say with Will it was an active decision.  He said he understood and we chatted about other things after that.

 

Later that week, John invited me to a bbq he was having.  His parents would be out of town and he was having a bunch of guys over to hang out, drink, smoke a little, and that I should definitely come.  I was nervous about meeting him in person.  What if he didn't like me once we met?  What if his friends thought I was ugly?  What if...What if...etc???  These are all things I thought and never said to John.  Instead, I said what do your friends know about me and he said that you are hot, tall, smart, and a good guy.  I asked if they knew what I'd told him about getting barebacked.  He said, "No way.  That is our secret."  I told him I'd decide that weekend based on my workload  but I really wanted to meet him and he said he hoped I'd come.

 

 

 

The Party That Changed Everything

 

I decided to go to the party.  I thought it would be great to make some new gay friends since I still didn't really have a "core" group to hang out with regularly.  I was also really excited to meet John.  I didn't know if we'd date, have sex or just be good friends, but I really wanted one or more of them to happen.  I was also nervous because I was worried he wouldn't like me, etc.  It was really warm out, so I wore a tight polo shirt and shorts that showed off my ass.  I also brought a small trunk bathing suit with the "football pants" ties in the front and a tank top in case we swam.  John had also said I could stay over if I was took drunk to drive home.  So I brought another shirt too.  (I am kind of a clothes fanatic.  I like to look good.)

 

I got there and I was really nervous.  I waited outside for a minute in my car thinking I would just leave.  Instead, I saw some hot guys going in and I decided to get out of my car.  I rang the bell and John opened the door.  God he was fucking gorgeous.....he looked exactly like I'd always hoped he would - the high school baseball star, but aged 27.  He was excited to see me and gave me a huge hug.  I was so relieved.  He took me out to the deck where guys were chatting and hanging out, swimming, drinking, etc.  It was like everyone knew each other.  John said they all knew each other from dating, the suburban bars, high school, etc.  Every guy was bi or gay.  So many hot guys.  John could see I was nervous and a bit out of place.  He took my hand and said, "You are so hot.  I'm so glad you came.  Let's get a drink and I'll introduce you to people."  

 

We got vodka lemonades, I made mine strong to calm my nerves.  He introduced me around and by the time we got back around to the drinks, his two best friends were in the kitchen.  He left me with them and I had a couple more drinks with them.  Greg and Andy, the best friends, and I decided to go swimming because we were drinking too fast.  They already had their suits on and I said I needed to change and Greg said, "Just go naked."  We all laughed.  I went to the bathroom and slipped out of my clothes and into my suit.  I came out and the guys in the kitchen stared.  Greg sad, "I could tell you had a great body, but damn John can pick the hotties."  I blushed and a few guys said they liked my suit.  We went out to swim.  It was fun.  We laughed and played around and eventually Andy and I were in these floating chairs.  Greg or one of the other guys brought us drinks when they refilled.  It was an easy day.  

 

I was getting a little drunk and the food was ready.  We went inside and a few guys were standing around chatting and eating.  One of the guys was telling a story about a really slutty hookup of his that he met at the bar last weekend.  Brief story, the storyteller who was totally hot - short, tan, ripped body and a good solid face - said he met this dude, they danced, and then went to the parking lot and instead of leaving, the guy let him fuck him right there.  The storyteller ended by saying he was such a slut, he begged me to cum inside him.  One of the guys said, "Did you?"  The storyteller said yes.  I was getting a bit hard, but hidden behind the breakfast bar, my increasingly hard cock was hidden from view.  John appeared next to me just as the conversation became one of safe versus bareback sex.  Most of the guys said they only did safe sex.  The storyteller called out one guy he'd fucked bareback and the guy blushed and agreed he had no always used condoms.  Greg and Andy and John all said that bareback sex was hot, but they usually did it with condoms.  Everyone seemed to look at me at one point and I said, I always use condoms.  I was so embarrassed that I'd had to say anything.  John put his hand on my ass and squeezed.  I looked at him and he winked.

 

After that, the party broke up into groups again.  People swimming, drinking, the music got louder.  I was hanging out with Greg and Andy and John.  Greg got his pipe and we smoked some pot in the back yard while sitting in some awesome patio chairs.  I was high and kinda drunk by now.  Greg was generous with his stuff.  He was really nice.  I was now only in my tank top and swimsuit.  Greg brought the conversation to tops and bottoms.  Greg and Andy were versatile and had fucked each other a few times.  John was almost always a top, but had tried bottoming.  I admitted I was almost always the one getting fucked.  Then Greg, who I guess was the aggressive one of the friends, brought the conversation back around to the bareback discussion.  Under some pressure from the guys, I admitted that guys had fucked me bareback.  Greg was interested and asked me details.  I shared as we smoked some more.  John was smiling and said, "I was keeping your secrets, but get you a little drunk and high and you open up so easy."  We all laughed.

 

At this point, it was getting dark and the party was breaking up.  Some guys had other stuff to do and still another larger group had planned to go out to the bars after John's party and John let them all get changed in his house.  It was now down to Greg, Andy, John and myself.  John said, "We have a ton of booze left, let's get drunk and everyone can stay over."  I agreed.  We helped John clean up and hung out on the deck drinking and talking.  I was getting cold so John told me to come upstairs and he'd try to find something to fit me (I'm 6'2".  He's 5'11".  Might be a challenge.)  We went upstairs and we quickly found a tee shirt and light jacket, but the pants were an issue.  We ran to his brother's room (in Europe for the summer) and he came back with some sweat pants that barely fit me.  He said, "Sorry best I can do."  I dropped my swimsuit and put on my briefs and the sweatpants.  That's when John kissed me.  I was really turned on and kissed him back and we made out.  After a few minutes John said, "Let's go back downstairs."  He put on sweat pants and sweat shirt and we went downstairs.  The other guys had jackets or jeans on because they were cold too.  

 

We had some more drinks and then Greg says, "Look what I found in my jacket pocket?"  It was a little bag of white powder.  He asked us if we wanted to do some lines of coke.  I admitted that I never had.  The other guys said, "Don't worry.  We'll take care of you if anything goes wrong."  I was nervous but I did the lines with them.  I was high as fuck from the booze, pot and now the coke.  I was also so horny from being around the hot guys in swimsuits and making out with John a few minutes earlier.  

 

I went back inside to make drinks and John came with me.  He asked how I was feeling and I told him I was good, but really high and horny.  John kissed me again and we went to the living room to make out on the couch.  Our clothes came off pretty fast and soon I was straddling his lap in just my underwear.  He was just in his sweat pants.  I do remember that he didn't put on underwear earlier because I could feel his hard cock pushing on me through the sweat pants.  The other guys had come in to get drinks and see if we were alright.  They saw us making out and Greg laughed and said, "Alright John!"  Andy punched him in the arm and they just watched.  I was so high and turned on that didn't care.  

 

After a while, my underwear was off and John's cock was out of the sweat pants.  He bent me over the couch and started eating my ass.  I could see Greg and Andy kissing and they were stroking each other's cocks, but they were really watching John and I.  John ate my ass like it was his fucking favorite thing to do.  He stayed at it forever.  I remember giving him head, but not as much as I remember how he ate my ass.  I was pulling my ass cheeks apart as far as they would go.  He was definitely inside the outer sphincter penetrating me with his tongue over and over like he was fucking me with it.  I was a fucking bitch in heat.  He stopped and laid his cock on my ass.  I looked back at him and said, "Condom and lube?"  He said, "No problem.  Be right back."  Greg and Andy came over at this point and ran their hands over my ass, but nothing more.  They went over and sat on the other couch and took off their pants and kept stroking their hard cocks.  

 

John came back and lubed my ass and I lubed his cock and he called his friends "pervs" but didn't tell them to leave and neither did I.  He sat on the couch and handed me the condom and I straddled him and we made out some more.  At this point his friends were directly behind me about 8 feet and I couldn't care less.  I wanted John so badly.  As we made out his cock kept rubbing against my ass and on my hole that he had opened up so much.  I still had the condom in my hand.  He reached down and held his cock to make me moan more as I rubbed my ass on it.  I kissed him hard and just started to back my bare ass down on his cock.  He looked into my eyes and I just kept sliding down.  I winced and halted and he grabbed both my hands.  He could feel the unopened condom in the one and squeezed that hand.  I slid my ass further down on his cock and said I want this.  He moaned and let me start riding his cock.

 

I heard his friends say something, but I didn't care.  I was just loving riding John's cock.  it was 7" cut and felt good sliding in and out of my bare ass.  I didn't care that his friends saw be getting fucked barebacked.  John bent me over the back of the couch and started really fucking me.  At this point Greg came around and put his cock in my face.  I started sucking his Greg's cock.  Now I was getting spitroasted by these two guys and John called me a slut and said my ass felt so good.  He fucked me for like 10 minutes and I was sucking Greg and licking his balls, but my focus was on John so I'm not sure how much attention Greg's cock was really getting.  John said, I'm coming and he blew his load in my ass.  He kind of collapsed on top of me and kissed my neck.  I stopped sucking Greg and kissed John.  John slipped from my ass and I turned over and he stroked me and went to suck me.  Greg walked around and picked up my legs and stood in front of me and pulled me forward until his cock was lined up with my ass.  I saw the condom on the couch between John and I and he saw me look at it and said, "No way am I using that after I saw you take him bareback."  He then slipped inside my ass.

 

Greg didn't last long and he came fairly quickly, but his cock was thicker.  John then fucked me again and came inside me.  Andy came by jerking off on the other couch watching us.  I came as John was fucking me the second time.  Greg and Andy fell asleep on the other couch and John and I went to his bed.  He sucked my cock in bed and I came again.  It was an awesome night.

 

I woke up before everyone in the morning and was taking a shower when I heard the door to the bathroom open.  It was Andy.  He said it was really hot watching me getting fucked last night.  He also said he's glad I felt comfortable enough to let him watch.  Then he got in the shower with me.  Andy pushed me against the wall and said it was his turn to fuck me.  He was such a nice guy but this aggressive side was hot and I got hard.  He squirted some shampoo on his cock and slid it in my ass.  He said, "I'll be quick because the shampoo will burn in a bit."  Andy just went to town on my ass.  He fucked me hard and quick and then came in my ass after only a few minutes.  I was so turned on that I came on the tile wall.  After we finished Andy picked my cum up with his fingers and ate it.

 

It was an awesome morning.  We drove to the city and all went to brunch.  John, Greg, Andy and I hung out until mid afternoon and then they went back to the burbs.  John and I chatted again after that my phone and email.  He said he felt uncomfortable dating me because I'd let his friends fuck me bareback.  He said I was too slutty for him, but he wanted to be friends.  After that conversation, our friendship fizzled.  Greg came into the city to go to the bars a lot more than the other boys.  He often slept over at my place when he didn't pick up a boy and he fucked me a lot.  I always took his load and never asked him to use a condom.  Greg disappeared from my world one day and I haven't seen him since although he and Andy still talk sometimes.  Andy and I only fucked a few more times including a couple of 3somes with Greg, but Andy got a boyfriend by the next year and they moved to Hawaii and got married.  Seriously, Andy is an awesome guy and we are still friends.  I'm not sure his husband knows all about me, but once when his husband was drunk he called me a cum dump and I just smiled.

 

John's party basically blew my mind.  I almost never used a condom since I slid down on John's cock with the unopened condom still in my hand.  There are a few more stories of me slipping further into being a cum dump from my online hookups which became more frequent, to boyfriends, to poz guys, to my first real fuck buddy.  

 

More to come......I hope you guys still like it.