Best and worst...

Explain in as much detail as you can remember, the best blow job you ever got and the worst.

 

Oh my, I've had so many in my life time it's hard to remember the best and the worst. I have had far more good one's than bad one's that's for sure so I guess I can start with describing the worst.

The WORST: (as you put it) but actually IMO I'd call it the least pleasurable with a happy ending. This girl in High School whom was pretty flat chested in 11th grade returned her senior year to have blossomed some very attractive sized breasts and was obviously proud of them wearing what was popular at the time "tube tops". They were very attractive and her nipples were always protruding within the fabric. Anyway, she had always been considered a friend but never in a sexual way until one afternoon she just came right out and asked me if I would like a blowjob from her. I certainly wasn't going to say no so I offered to walk her home. We get to her house and we walk into the back yard where she immediately drops to her knees and begins opening my pants and takes my flaccid dick into her mouth and power sucks it like a hoover vacuum cleaner. At this point I'm not complaining as she's gobbling up my quickly hardening cock but then I'm feeling some serious teeth drag as I pull out of her mouth to complain. She apologizes and goes back down on my cock to once again drag her teeth along the length of my shaft which is ruining the moment so I pull my now hard cock out of her mouth again and convinced her to suck on my balls as I stroked a load out on her face. I thanked her for her efforts but also let her know she needs more practice.

The BEST: This one is an easy one to remember but not my proudest moment being I was married and my neighbors wife wanted to give me a blowjob and I was not going to refuse it. We proceed to our family room as I sit on the couch and remove my pants as she anxiously gets on her knees between my legs and starts liking my balls, then up the length of my shaft to the helmet where she works her tongue around it and slides her dripping tongue back down my hardening shaft to suck on my balls for a while gently stroking my cock hard. And then she smiles and begins smacking my cock against her tongue and says "Are you ready?"...Oh yeah and down she goes and take my 8" to my balls as her tongue slides out under my sack...Oh shit I say...and she proceeds to repeatedly deep throat my entire cock 10-12 times before sucking on the entire length and then deep throats me again as I was gone and blowing my load down her throat as she forced her face against my tummy and pulling my ass cheeks tight against her face until I was finished cumming. She slowly comes up keeping a grip on my cock with her lips and tongues my helmet to say "Mmmm, that tasted good!" She continued to tongue and suck my softening dick as I feel it becoming firm again which she says "Oh, it wants more" and back down on my cock and sucked that thing for another 25 minutes until I shot another load in her mouth. That woman could suck cock!

 

WORST: Definitely the 5 minute helmet lick that my ex tried. The one and only time in our 10 yr relationship. And every second was torture to her. So I never asked again. BEST: Wow, that's not an easy one. I will say it's the time I came the closest to blowing my load. We were both extremely sassy and horny that day, teasing each other and hands under the clothing constantly when nobody was looking. We're at her mom's house, and her mom was taking a quick walk to the end of the block and back. The second she walked out that door we were like clothed animals on that couch. Hot deep kissing with nails grabbing our backs, grabbing her boobs and nipples, her hand stroking my cock in my pants, (constantly glancing out the window for her mom). I seen her mom had turned around and on her way back, so I grabbed her head and whispered in her ear "your mom is coming, and so are you" I spread her legs, grabbed the hair on the back of her head, and started spanking her pussy. In seconds she squirted and soaked right through her jeans! Her mom was coming up the driveway, she ran to her room and the bathroom while I flipped the wet couch cushion over. We barely made it out of that one lol. We said goodbye and went straight to the motel room. Our clothes were flying off as we were walking in! She dropped to her knees and took every inch to my balls. I continued to guide her head and fuck her mouth and throat with those eyes staring up at me. Then she would take over. After a half hour I was getting those wonderful pre-orgasm tingles and sensitivity. She already had a couple orgasms due to her love of sucking cock. And that was when we got a knock on the door, I said yes? "HOUSEKEEPING" OMG it couldn't have came at a worse time!!! I had to yell that we're fine and don't need anything. We continued on, but that 10 second break and mental interruption was enough to let those tingles go away and never come back. 15 minutes later I could tell she was slowing down and getting tired, so we just pounded doggy with her squirting everywhere over and over until she milked every drop out of me. I know, more of a BEST AFTERNOON than best blowjob lol. But I figured I'd just share the entire experience

 

BEST

She was a long time friend that i'd had an on going affair with over the span of 5-6 yrs or so. From the start she'd always given AMAZING blowjobs and said her husband didn't like BJs but she did so she enjoyed giving them but she would never finish me, said she didn't like the taste or texture of cum, which i could respect.

i was 25/26, After 4yrs or so she finally divorced her husband, we continued fucking and she started dating again. One day she stops by my place looking hot as fuck, i try getting some and she says she was just stopping by to say hi and kill some time before her date and i wasn't getting any because she planned on fucking the guy that night, i still kept at it and we start making out but she insists i'm going to have to get myself off when she leaves, i knew how to get her going and soon enough i'm fingering her and convince her to let me eat her out, she ends up having one hell of an orgasm and says she'd feel bad leaving me hard after that so she'll get me off, i think we're going to fuck and she stops me and says no she's going to give me a blowjob, i was a bit confused and reminded her she never let me finish in her mouth, thats when she says she had a date a couple weeks prior and she gave the guy a blowjob and he came in her mouth unannounced, she was pissed initially but was actually turn on by it and didn't hate the taste or texture as much as she thought. So i sat back as she started to do her thing and i warned her i'm kind of a heavy cummer, seeing as we'd always used condoms and she'd never seen how much i cum, she insists she can handle it and goes to town, it was phenomenal as always, but it got better, i could feel it building and instead of stopping like i was used to she kept going, faster and deeper, her hand stroking in sync with her mouth, i was getting closer and started warning her and she just started going faster then it hit like no orgasm i'd ever had before, cock and balls throbbed as my hips thrust my cock involuntarily into her mouth deeper, now this is where most women would stop and just let it subside, however she was caught off guard by the mouthful and kept sucking and stroking as she struggled to swallow my cum, i was so sensitive i felt a second orgasm hit at which point to this day i swear i momentarily blacked out, when i opened my eyes she was sitting up watery eyes and gasping for air and asking what the fuck was that, i asked what she meant and she said she honestly thought she was going to drown from the amount of cum coming out of me and she'd never once seen a guy cum so much at one time. She went on her date, the sex was apparently lousy and we continued fucking as always and she couldn't suck my cock enough although it never reached the level of that first time.

WORST

She was my Tswift look a like fuck buddy, i was looking for a booty call one night and got her to stop by on her way home, we start fooling around then she tells me we can't actually fuck because shes on her period. Now this woman gave mediocre head at best, but i was horny as fuck and she'd come over, gotten me hard only to tell me we can't fuck, so i said well she got me hard so least she could do was give me a blowjob, she was hesitant but agreed got down on her knees and started sucking, i'm not sure what i expected but after almost ten minutes of this half ass blowjob i was ready to finish but she wasn't getting me there so i reached down and started jerking off to get myself close enough she could finish, i asked where she wanted it and she shrugged her shoulders and gave an uncertain "in my mouth" , well i got myself 95% there and she took over, when i told her i was about to cum she didn't just take the tip she took as much as she could and again, heavy cummer that first spurt was more than she could handle, she coughed, pulled my cock all the way out but held onto it and i guess was not aware there was more coming and took another 3-4 spurts to the face, needless to say she was a bit pissed about the facial but that was all her doing

 

OMG I was LMAO! imagining both of those! That's definitely not the way to be caught off guard.

 

oh it was hard to hold back the laughter with the worst blowjob chick, i mean she had a solid facial and it was even in her hair and her reaction was just complete shock

 

The best, hmmmmm......The first time I got to cum in her mouth and she swallowed it. It was that cute but a little chubby girl down the hall in college, she was always flirty, she said she wanted to show me something, and just come on over tonight. I ended up sitting on the edge of her bed, her sliding my pants off, I was so hard that my cock sprang up to her face as she slid the waste band over it, boing... She licked the tip a little, played with my balls, jerked it a bit, and then she just really went to town sucking my cock, she had obviously hd a lot of practice. I mean, I'd had kind-of blowjobs from girls in high school and my girlfriend, but this girl could really suck - and was crazy into it. I had those two big bubbly tits of hers in my hands, her head bobbing up and down with that bowl haircut, her tongue doing things I'd never felt before. It was feeling so intense, but I was a gentleman and told her I was cumming (as if she couldn't tell from my lack of oxygen), expecting her to pull off, dodge it and make a mess like my girlfriend always would before, but then she grabbed onto my ass and just kept sucking...I tried to hold it but had to let it go and she just sucked it all out of me and swallowed it. I came so hard, I almost passed out - for one, the orgasm was so intense and long, and two, stunned in disbelief that she made me to and wanted me to cum in her mouth - and then swallowed it all, just like 'yep, that's how it's done' !! It had to have been a lot of cum from it being so good and it was just gone - not a drop anywhere. She was the first girl that did that for me and she ruined me for life. She never wanted to do it again, tho....maybe she thought she was giving lucky boy a gift....but damn....

The worst....hmmmmm......I've never had a BAD blowjob, but my 17 year old girlfriend's first attempt was like, ok, my mouth is on it, how is that? But a few times she finally figured it out but she wasn't up for cum in her mouth tho.....I think she would have eventually, but we went our different ways...

 

The worst was when a girl started sucking the head so hard it hurt! I had to stop her. I got a huge dark purple hickey on the head from her attempt. It hurt for a few days like a bruise and it was no fun to endure that discomfort. Once and done for her.

The best - that's easy. My wife.

 

Funny enough it was off a girl that had only been with a couple of guys before and was really insecure and nervous about having sex. Im circumsiced so it takes a lot for bj to be mind blowing, but she was incredible! Used to be difficult last long at all!

 

Worst was a girl I met while on vacation in Cancun with my family right after high school graduation. She was with her family. We flirted for a day or so and then I ended up taking a walk on the beach with her late one night. After a serious make out session I went down on her. After she came I expected my turn. She said she couldn’t do that on a breach when anyone could walk by (at 1:00AM??). We couldn’t go back to her room (her brother was there, and we couldn’t go back to my room (two of my brothers there). So I was left with a serious case off blue balls. The next day everyone was at the pool and she said it was time. With everyone else poolside we went to my room. She knew what she was doing, but everytime I’d moan, she’d stop. Then she’d start again. I’d moan and she’d stop. So I stopped moaning. A minute or two later I started to cum without making a sound. After the first squirt she pulled back all pissed off because I came in her mouth. She stormed out of the room leaving me with a puddle of cum on my belly.

The best was my girlfriend when I was 19. She was 21 and was very comfortable with her sexuality. She was the one and only woman I’ve ever known that actually preferred giving blowjobs over her own needs. Believe me, she was needy, but she absolutely LOVED giving head. And after I came, she just kept sucking. Fortunately, I was 19 and my refractory period was about 10 minutes. And after cumming in her mouth, I could last just barely long enough to make her cum (always doggy style - funny what you can vividly remember decades later!). And after pulling out of her she always spun around and insisted on cleaning up. God I miss her! My wife is great and I have no regrets, but that one GF was the best sex I’ve ever had!

 

The best was a coworker in my office. Leaning against my desk pants at my ankles. She was licking everything right. Balls. Taint. Stroking. She told me she couldn’t swallow because she was meeting her husband for dinner after she was done. I said bullshit you’re taking my fucking load. I started cumming. She took half in her mouth. The other half hit her shoulder and wall behind her. She cleaned me up. And said that’s the biggest load she’s ever seen. And I ever jerked off that morning.

the worst....a girl in high school. Said she had never done it before and wanted me to teach her. She used her teeth way to much. Had no rhythm. I tried to tell her how I liked it. But she just wasn’t getting it. So I made her lick my balls while I jerked off onto her face. Actually saw her a few years after high school at the store. She made it known to me she got better and gave me her number. I never called....

 

Best was first time I had 2 girls at thee same time.

 

^^^^^ OK - Now you pissed me off ……………. sort of!!! That's been my fantasy for ……………. life!!!

 

Ahem......it's been every man's fantasy..........only problem I would have would be deciding who earns the load.

 

"What did you learn in school today, Johnny? " ……………………………………………. "Sharing."

 

Wish I went to THAT school...............

 

Ahh yes, the old surprise cumshot. Nice work! I've seen a few videos where this happens and they're usually very funny.
Great that your worst blowjob experience still resulted in giving her a massive facial. I guess she deserved it for giving lousy head.

 

WORST:

One-night-stand with a 20 year old girl who was apparently engaged to be married. She wanted a fuck, but didn't seem very horny. Maybe she just thought that's what you do on a night out. She was blonde, quite chubby with decent tits and a nice round fat ass. Wasn't particularly cute but I liked the idea of her cheating on the fiancée with me. I got her home and we sat on the bed making out. She popped her tits out for me to play with.
I asked her if she wanted to suck my cock and she said something like "do I have to?" ...She obviously wasn't thrilled with the idea but got down on her knees in front of me. I presented my dick which was hard and wet with pre-cum. She closed her eyes and reluctantly took my head into her mouth. That was it. She didn't go any further and barely did any sucking. Basically just held it there. I had to gently push her head down to get just a centimeter more into her mouth. She wasn't into it and stopped after about a minute. It was hardly even a blowjob, just some brief sucking.
Then I got her naked and made a point of spending a long time eating her pussy to show her that oral could be fun. I instructed her to bend over, she obliged and presented her big ass. At some point she said "no swallowing and no anal", which was a turn off. I started fucking her from behind, hoping to make her cum but she barely made a sound. I kept pumping for a while until it became boring so I focused on her lovely fat ass until I was very close to cumming.
I instructed her to roll over, she did so and before she knew what was happening I was on top of her jerking off. I started to cum in her face and some of it landed there but she raised her hands and blocked the rest of it. I finished up and climbed off. Seeming quite annoyed and disappointed, she said "why do guys always do that!?" I told her that she looked good with cum on her face. She was not amused.

BEST:

My previous girlfriend was an expert at performing oral sex. She loved to suck cock and loved to eat my cum. Every blowjob from her was an event but a particular one stands out. She was at work feeling horny and began to send me suggestive text messages. They were quite explicit, I remember her text said "I'm going to take as much of him into my mouth as I possibly can and keep him in there until he explodes". Based on what happened when she got home, she'd obviously been thinking about this all day.
I was at the window when she arrived, having just finished smoking a spliff. I'd momentarily forgotten about her plans, which made the experience a pleasant surprise. She opened the door, didn't say a word, walked across the room and began kissing me while rubbing my cock with her hand. I got hard quickly and she gave me a devilish smile. She went down on her knees, opened my pants and got my dick out. It was twitching and very wet. Without missing a beat, she immediately took me into her mouth.
Normally she would build up to it but this time she swallowed my entire cock as soon as it entered her mouth. The girl had incredible deepthroat skills and could fit all of my 6 inch penis in her mouth. She would gag occasionally but never had to stop sucking. With her pressing her face against my belly and slowly sucking on my throbbing erection I could feel the back of her throat. She didn't once use her hands, instead resting them on my hips. I hadn't moved from that spot and just continued standing there with my dick out and this beautiful girl on her knees blowing me as if she was starving. Still wearing her work blouse and glasses, she looked sexy as hell. Slightly chubby with an attractive face, lovely big tits and a fine ass. Really kinky too.
Pretty soon I could feel an orgasm approaching. She was aware of it too and increased the speed of her sucking. It got to the point where I couldn't hold it back any more and I ejaculated in her mouth, having an incredibly intense orgasm. She pressed her face hard against me so I was cumming straight down her throat. She liked to make me cum without any assistance and her facial expression looked like she was having an orgasm too. After swallowing my load she continued sucking for a few more minutes, relishing the experience. She hadn't let my cock out of her mouth the entire time and I didn't have to do a single thing. When I finally became soft she let me slide out of her mouth then looked up and smiled. I stared back, almost in disbelief as my body quivered and I tried to catch my breath. She stoop up and we kissed some more, sharing the taste.

Sadly the relationship ended but fortunately I filmed many blowjobs and facials, even some anal sex with her. If anyone would like to see what I'm talking about, pm me and I'll send you a link to the videos. Great thread here, thanks!

 

Best? Getting a tit/blowjob from a cougar who had a set of huge, soft tits. While I was sitting on one of her dining room chairs, she sat her tits in my lap and blew me while my dick stood up in between them. When I finally started to cum, she mushed her tits together around my dick and started doing this quick-sucking thing on the head while I shot in her mouth. She basically milked me for every drop and swallowed the entire load while looking up into my face. The best orgasm from oral I’ve ever had hands down.

Worst? Getting thrown up on. The chick got too drunk and started blowing chunks on me smh. It’s was really bad and kinda pissed me off too because it came outta nowhere and happened in my car. And no I didn’t finish lol

 

That gets my vote for the worst!