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Bears Your first experience with a bear / daddy?

bigboi229

bigboi229

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I had my first real experience with a daddy bear tonight. It was pretty hot...this guy didn't wanna top me, though, but I did get to suck his cock & swallow a HUGE load. He was really sexy, too, in his mid-50's & very hairy. Anyone else willing to share their first time stories with bears or daddies? :-)
 
First Time with Daddy

I met him on Squirt. I was a little nervous, because I'd only ever been with one guy before, and we had been friends already. This was a total stranger, but his dick and body looked so nice in his online pictures and I was so fucking horny from trying to be celibate for Jesus. (God, what a life.) We exchanged phone numbers and he called me up. One thing that comforted me about getting together with a total stranger was that he asked me over the phone if I was a freak. That reassured me that I wasn't in for anything weird.

I drove to his place, and a regular guy with salt and pepper hair answered the door. He invited me in and offered me something to drink. We told each other our first names as I stood in his kitchen, nervously sipping some water. Then he blurted out, "So you wanna get naked?" I excitedly replied in the affirmative, and we walked back to his room. I pulled off my shoes and socks while he walked quietly over to each bedroom window and secured the blinds. Then I met him in the middle of the room, put my arms around his waist, and kissed him. I reached down and grabbed his hard dick through his jeans. He started grabbing me all over. I reached up under his shirt and squeezed his pecs.

Pretty soon I was on my knees as we both fumbled with his button and fly. He whipped it out and I went down on him. His dick was (and still is :)) big. I took as much of it as I could. He sighed pleasurably as I licked his cock. Then I stood up and he put me in his mouth. This is when I started to discover that I prefer the bottom, because I didn't react as much to having someone suck me off. But it was nice being that intimate with someone.

I don't remember all the details after that, just images of us shucking off our pants and underwear, rolling around on his bed, doing 69, him holding me tight in his arms while lying on top of me and rocking back and forth.

When it was time for him to cum, he sat up, pressed his upper thighs into the back of my legs as I lay on my back, and I pulled on his cock until I saw his semen released. He shot it on my pelvis next to my dick, and some on my stomach. I mopped up a bunch of it with my fingers and licked. He didn't (and doesn't) have any of that tangy detergent taste. His is like a nice Italian sauce. After he got done breathing heavy and moaning, he said what he usually says: "That was hot!" I didn't cum that first time, and I don't often cum with any guy. But the memory of it gets me off whenever I need it.

At some point during the afterglow, we got around to giving each other more personal information. I actually confessed that I was a Mormon (feeling dirty for what I had just done), and he told me he had been raised Catholic, so he was sure the Pope wasn't too thrilled with what he was doing. That made me feel a little bit better.

Over that weekend, we did it several more times. The last time that weekend, I told him to cum in my mouth when he was ready, and not to wait for me. He did, and I swallowed it all. After that, I lay on his stomach, fondling his softening dick while jerking myself off. When it finally became my turn, I moved up on the bed and put my dick in his mouth. He took my entire load, which was pretty voluminous. (He even coughed a bit when he swallowed, and commented on how much I came.)

Maybe now you see why this guy is still my favorite fuck buddy.
 
I remember the first time I went cruising downtown. I saw this guy in a mini-van. He was a little chubby and had a beard (which was an immediate attraction). We stopped in a parking lot and talked for a second, just to make sure we were both legit (not police). He knew of this secluded parking area, so we went there. I was so nervous when he got in my car. We started touching and kissing. His beard was such an awesome feeling on my mouth. I was in heaven. He pulled his pants down to reveal a chubby cock. It was about 5/6 inches, but fat. I sucked that cock like their was no tomorrow. When he came, I wanted it bad. Swallowed every drop, and it tasted so good. He then gave me some good head as well.
I saw him many times after that, but when the cruising area became infected with police, I never saw him again. Hell, I can't even remember his name, but he was very sweet and gentle. Especially it being my first time with a man. Awe, the good ole' days.
 
It was two years ago... i just came out and well... registrated at a gay dating portal though i was only 16 ;)
some days later he messaged me and asked if we'd like to meet each other... i was totally impressed of his pictures (no nude ones) and he told me he was 28 yrs old.

when we met in a cafe we had smalltalk and then went into a cinema where we started kissing around. i was so excited because it was my first time with a man.
later he drove me home and i told him to stop at some fields where neither a house nore light was to see... we kissed an i told him i was getting cold outside (it was winter) so i'd like to be in the warm car with him... well ;) we sucked each other for about one hour and kissing around etc. It was my first time having sex and it was wonderfull. we then met regularly and some weeks later he told me he was 39 Oo

Well... i felt a bit sick but i told him it is okay and it wouldn't change anything...
now i'm in love with him for over 2 years and my parents still think he is 30 :^o
 
I was 18 and I went to a public restroom at an office building (with some shops on the lower floors). At the time, I was a virgin, 145lbs, 5'10"...I didn't realize that some daddy types were even interested in my type. On my way to the men's room, I walked by this guy who was standing there talking to a sales girl in front of a store. He stared at me and I thought...that's weird. I looked back at him wondering "do I know him?" I went into the men's room and went to a stall. He followed me in a few seconds later and stood at the urinal across from me. He then turned around and stroked his cock outside the stall, so I could see him through the crack in the door. I COULDN'T believe it. I was STUNNED. He was about 45, brown hair, beard, hairy, with a big dick. I unlatched the door and he came in with me...He didn't say anything, but grabbed me and started french kissing me...I ran my hands up under his pull over shirt and felt lots of hair...pulled my shirt up and his shirt and felt his hairy chest against my smooth one...he grinding his dick against mine..clutching my ass. Then, he started to jackoff - shooting a huge load into the toilet. When he had finished, he pulled up his pants and RAN out of there like he was on fire. I was very confused, but that's what started me on chasing hairy men. He was my first experience and I LOVED it.
 
My first bear was also my first sex as an adult (previos to fooling around with a cousin, my brother and a neighbor). There's a thread around here about the "first cock you sucked" and that would be him. He was maybe 45, stock, not too hairy, mustached and bald. If anyone is familiar with matureaussie you'll get a rough picture of him, just a little darker skin, and with a bigger cock (unless my memory is playing tricks with me. This was 20 years ago).

Anyway, I was 19 or 20. He first sucked me dry in a book store I was minding. but after an aborted attempt at sucking him off in the front seat of my car in a not so secluded spot, I felt ashamed about it all and threw his number away.

Fortunately I met him in a coin and stamp store some months later and, being more horny than prudish than the last time we met,I took him home (knowing my family was out shopping). We stripped in my bed and I went down on him for a while, but then asked him if he wanted to fuck me (I had been craving to get fucked for most of my late teens. Flat on my belly with his body on top of mine and his cock completely in me was about as defining a moment in my life as any. We tried a couple different positions (and I found out riding a cock cowboy style just isn't as easy as it looks). He came by his own hand while kissing me. We had two more encounters after that in which he gave me my first mouthful of jizz.
 
He was a construction worker late thirties,tall,wide,hairy,tattooed and very rough....i was sixteen,smooth,toned,a virgin and sore for a week!.
 
wow, this thread is really hot:-P

so my first time with a daddybear was when i was 17 and meet this guy i met on gayromeo.com

we've been chatting for several months and when he was close to my city he decided to take a hotel for one night and wanted me to come to his room... what happened then was pretty hot:-P and he took the room for the next night too:-)
 
I was 14 he was in his low to mid 40's, he had a child older then me by like 6 years. He was my father's co-worker/employee, he used to massage my feet, suck on my toes, it felt so good. Then one day he was giving me a massage while i sat on the floor and him in a chair at my parents business, and put my foot into his crotch to massage my toes and ankle. Lets just say that I felt something very hard in there lol... So later I had set a plan to get him to drive me to the mall, and then after ask him about him. So after we left the mall, I asked him for a piece of paper and wrote down "are you gay?". Reason why I thought so was because of the attention to my feet and the one day where I felt his hard on with my foot.

He replied with, "Why are you?". I started crying because I didn't know the answer but most importantly because I was embarassed. So we got in the car and drove off. I was still crying so he put my head in his lap while he drove (he knew what he was doing haha), and he started to rub/caress my hair and head. It felt great and I was getting pretty hot about it, so i grabbed his hand and sucked on his fingers (I saw it in a porn somewhere). A couple minutes into me sucking on his fingers he forcefully turns my head so my mouth is directly on his crotch, I knew what to do from there due to the movies I have seen So I started licking and sucking on his bulge, then unbuttoned/unzipped his pants, took out his cock and started sucking on it. While I was sucking his cock, I felt a sharp turn so I got up and saw he was now on a road that was deserted. We got to the end and he parked. He asked me if I knew what I was doing and I said yes and went back to sucking his cock. About 25 minutes later he finally cums and I swallow it. A few weeks later he fucked me, or so he says I didnt feel anything and this guy has a big one. This guy is also still the record holder for longest blowjob I have given, with 2 hours giving head to him non stop lol, yes he cummed a few times :).

But I broke it off with him about a year after all of this. Reason why is because he was always interested in my older brother, I told him no way will it happen. So he took it upon himself to ask my brother to suck his cock, my brother said fuck no and he told my brother "why your brother already has." So I broke it off because he outed me. But somehow I think I pulled it off keeping me as straight to my families eyes. He would come around the store a lot even though I told him not to. To make things worse, my parents gave him a huge money loan to buy a house and they had a contract, so I saw him a lot more then I wanted to, and everytime I did see him, he would always bother me about getting back together and also try to take my shoes off as he has a serious foot fetish. So I stopped going to work for my parents and why I now run their business in a different state. But I saw him about 3 years ago at a show, he still looked hot as ever, a little more rugid, and still wanting me. He asked me to go on a cruise with him, then after we would have gotten back, he wanted me to travel cross country with him as he was then a truck driver. He was originally Real Estate then computer tech, back to real estate then truck driver. I respectfully declined him. I dislike this guy a lot because of the whole outing thing.

But lately, I have been thinking a lot about him. Mainly because of the sex we had :). He was my first bear/daddy and first gay sex I have had.
 
Most of you guys are lucky to have such a wonderful first time, my case is weird

So i was and i had sex with my cousin and other kids from the neighborhood, i cannot call it sex, it was just the curiosity stage, cock rubbing thing, so one day while i was chatting on some straight channel, some one messaged me, and asked me if we can be friends, i accepted the offer and while chatting with him, he asked that if i have ever had sex with a male. I got bit nervous, and then told him that i have never had sex with a male. He offered me to try him out, I asked about his age and he told me he is 34, boy i was nervous, but finally i managed to pass him on my cell number, he called me, and I had this weird feeling that something is not right, so over the phone we decided to meet at some public place, by 4 pm,
Nervous and anxious i reached there at 4pm and found no one of the said description, blue shirt and off white trouser, I saw a slim fellow with the same description and asked him if he is Mr.XYZ. He made a confused face to assure me that he is not. I was so fucking embarrassed that I managed to drive back and came back to the same spot after 10 minutes, so finally a person approached him with the same description. He had good looks, and a bearded guy. But when he said Hello to me, I realized that he has bad breath, boy I thought to run but again I offered him to sit in the car and talk, so he guided me to his place, and i told him that i will follow him to his place, once i park my car somewhere, while trying to find a place to park, i thought a thousand time to go back home, but my curiusty kept me stick to the idea of having sex. so he guided me to his place, and boy that was one messy room, he asked me to take off my shirt while he was getting naked, he wanted to kiss. but i refused, and then rubbed his cock against my smooth body till he came, i had my nostrils closed most of the time, due to his bad breath and body fume, Boy i immediately cleaned the cum of my body, and kit back and ran towards my car, to get home as soon as possible, back home i spent 2 hours in the shower till i finally felt that i am no longer smelling like him. Ewwwwwwww so after that encounter i met gorgeous old men. and i avoided blind dates since then.
 
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