Your Favourite Orgasm

I was reading an interesting article in this week’s Guide, the weekly television supplement from The Guardian newspaper, regarding the typical male’s competitive compulsion to create personal toplists for things like models, films or albums. Specifically, this article centred upon some new list show attempting to pick the greatest dance floor hit of all time (which, of course, would be Godley & Creme’s “The Room is Ready for Ralph”). However, there was one quote – highlighted in pink and set apart from the rest of the text – that really got me thinking: “Trying to identify the best dance record of all time is like picking your favourite orgasm.”

My mind immediately wandered to all of the orgasms I’ve enjoyed throughout my life. Thoughts & images of past handjobs, titfucks, blowjobs & pussy fucking flooded my sex-addled brain in chronological order – from the very first time my best mate’s girlfriend casually grabbed hold of my cock and began jacking me off, causing me to cum buckets all over myself from the first immensely horny feel of an unfamiliar hand, to the first “successful” blowjob I’d received to the first exquisite experience of cumming inside of a girl’s pussy to my first titfuck, the latter of which didn’t occur until much later in life due to the challenge of finding a pair of boobs big enough to pull it off (pun intended) to the present – and, being male, I naturally began ranking them in toplist fashion.

With oh so many excellent orgasms having occurred throughout my sexual history, I’m embarrassed to admit that it actually took a few days of carnal contemplation to come up with what I considered to be the best. First, I narrowed it down by category, separating out the titfucks from the blowjobs from the handjobs and the like (how sad am I?). I soon concluded that, although I enjoy the firm grip of a good handjob and the cock / cleavage interface of a tight titfuck, my orgasms had always been more intense when cumming inside of a girl’s mouth or pussy (who knows? it could just be the implied intimacy of invasive internal penetration).

So down to fucking & sucking, I began creating a further mental checklist comparing & contrasting the orgasmic potential of each. Whilst both offered the benefits of built-in natural lubrication and are decidedly less messy in terms of cumshot clean-up (especially in the case of girls who swallow), pussy sex provides the unique texture of a girl’s vaginal wall massaging your penis combined with the cock-crushing contractions of her own orgasm (the latter of which rarely fail to send me over the edge in a cum explosion). On the other hand, with oral sex I get the added erotic stimulus of the girl’s tongue licking up & down the length my swollen shaft and teeth scraping against the sensitive underside of my cock, not to mention the immense suction power of her mouth (and I do so enjoy having my frenulum sucked during the course of a nice, sloppy blowjob).

Ultimately, it was blowjobs that won out in the end, with one in particular standing out as my best orgasm of all time: Vix & I were sleepily spooning naked in bed, her tits pressed against my back (she usually prefers it from behind) with her arm draped over my torso so she could lazily toy with my genitalia (I’ve even awakened from time to time to find her wanking me in her sleep, leaving me to wonder what wet dreams she might be having). This time, however, she tightened her grip and used my cock as a handle to roll me onto my back, after which she mounted me cowgirl-style and commenced grinding her already wet pussy over my now throbbing erection, soaking it in her vaginal juices. This lasted for but a moment, as she soon repositioned herself, kneeling between my legs and licking my cock clean before sucking it hard into her mouth.

She held my spread legs down with her hands on my thighs and began bobbing her head up & down eagerly over my crotch, her lower teeth grazing my frenulum with every thrust as her talented tongue traced circles around my cock-head. Indeed, with all of the combined oral stimulus, it wasn’t long before she received the desired “hot drink through a fat straw” (which is how Vix referred to blowjobs when I first met her), sucking me harder than ever as seemingly endless waves of cum washed over her tongue and down her throat as she swallowed every single spurt of semen. Even after I’d finally blown my load completely, she kept hold of my spent cock in her mouth, now sucking me off more gently whilst lightly massaging its underbelly with her cum-soaked tongue and waited patiently until I at long last went limp within her (whereupon she loosened the grip of her lips on my flaccid shaft, laid back down, rolled over and promptly fell asleep).

And that was it – my absolute best orgasm of all time. However, everyone’s different and might not think blowjobs to be the be all and end all in terms of ejaculation locations. And so, I’ve prepared a little poll to find out what manner of sexual activity triggered your favourite orgasm. To demonstrate the various erotic possibilities in question, I’ve enlisted my favourite busty MILF who does it all with no-holes-barred (whom you may well remember from our last poll), 34FF Kelly Madison from

1. The Handjob

Handjob Videos with Kelly Madison at    Handjob Videos with Kelly Madison at

2. The Titfuck

Titfuck Videos with Kelly Madison at    Titfuck Videos with Kelly Madison at

3. The Blowjob

Blowjob Videos with Kelly Madison at    Blowjob Videos with Kelly Madison at

4. Anal Sex

Anal Sex Videos with Kelly Madison at    Anal Sex Videos with Kelly Madison at

5. Vaginal Sex

Vaginal Sex Videos with Kelly Madison at    Vaginal Sex Videos with Kelly Madison at



…granted, there are far more possibilities for achieving orgasm than the five exemplified above (i.e. footjobs, belly-fucks and the like), but I figure these would be the most popular. However, should your favourite cumshot have come from something completely different (thus the sixth catch-all category), please take a moment after you’ve cast your vote to leave a comment to let us know what particular perversion provided this ultimate orgasm so that we can all try it ourselves: ;~)

My favourite orgasm of all time came from…

View Results





MyBoobSite Update April 17th, 2009: Oops, wait a minute, I’ve got to change my answer now (although the poll won’t let me) as I’ve just had the most amazing orgasm of my life and it came from getting a handjob! :~o

My Favourite Orgasm

20 thoughts on “Your Favourite Orgasm”

  1. Wow – this is pure genius….and I LOVE the way that you’ve broken each type of male orgasm down into catergories – it would be rude not to. Otherwise, things become messy and random….and in the strict regime of order and kinky statistics that would never do :-) I think this vote could be outsourced to other blogs and the findings collected and mused over. I think blowjob or anal will come top – but I don’t think the local bookies will take my bet. I’ll keep popping in to check. Stay kinky xx

  2. Great job on this post! It was an interesting question. I was one of the few that voted “Something Else”. I think a few of my best were vaginal sex to oral sex before I orgasmed! It wasnt strictly one or the other that made it the best, Im pretty sure it was a combination.

  3. Love the site. Big fan of your HARD work on these sites. You make a lot of men proud of your handy work and effort to detail.

    I stated something else:

    It was back in HighSchool. Dated a girl who was not the most endowed up top, maybe pushing a B cup on her best day leaning over. Anyhow, there was this time my parents had left the house for the weekend, and bein 18 yr olds, we took the advantage of naked swimming and of course, fucking!

    Tanning nude was a favorite thing she would do and surprise me with her lack of tanlines when we used to strip naked and fuck every time we had a chance. That day was no different. Lots of lotion, tanned naked body.. lots of sex. After going for a while, she asked me to lay down and relax.. began to stroke me slowly, lotion laiden hands doing their magical work, until she inched over to me, spread my legs wider.. and took her feet, clean from the pool, poured some lotion on them.. and began to play with my cock. Running her big toe and inset tow up and down my shaft.. then both feet pressed together as she sat indian style.. up and down on my cock, pre cum glistening.. until I couldnt take it.. I creamed all over her feet. She giggled.. and jumped in the pool after milking me dry.. I will never forget that moment until I die~ Keep up the site Reese.. love it

  4. Reese, I have loved this site for a long time, too, though I never have posted before. But your poll got me thinking. I did come up with an answer (vaginal) and voted, but my overall thought vis a vis this question was that I don’t really remember my different orgams that vividly. I know I like orgasms, but I can’t really tell you about much difference between them. But believe me, I love sex just as much as the next guy. (I mean, I’m in the know about this site, after all!)

    But my answer is vaginal, and here’s the little story: Ex-girlfriend, but one I really liked. I was helping her do her taxes, ha. Anyways, somewhere toward the end of the taxes she and I start getting into it, and end up in the bedroom. What was most exciting about it was the amount of time we spent having sex. I came 5 times (in the span of perhaps 3 hours), definately a record for me. I remember the last one being better than the first. So it was that last one, and just the realization of how much fun I was having, how interested this girl was keeping me, that made that the best orgasm I’ve ever had (and can remember, ha).

  5. My all-time favourite orgasm? Reese, you have set some stern challenges in the past, but this one beats them all. Having said that, I have thoroughly enjoyed the reminiscing that this led me to over the last couple of days.

    While your description of the ultimate blowjob is very tempting indeed, for me the choice came down to vaginal sex and titfucking. The sensation of my wife’s oiled, pendulous boobs wrapped around my throbbing cock is second to none, as is the visual higlight of seeing my cum splattered all over her magnificent tits.

    But in terms of my favourite orgasm, I have to go for vaginal sex. This still leaves plenty of variations on a theme of course, so let me describe what for me has been a highly memorable experience. This may appeal to those who are more visually inclined…

    My wife loves riding me cowgirl style, grinding down on my cock so that it presses into her g-spot while she fingers her clit. The added bonus for me is that I get to enjoy the view of her big tits swaying directly in front of my face. As she gets closer to orgasm, I grab her hips and push deep, holding her there, so that I can feel her pussy contract on my cock as she cums. This is enough for me to shoot my load deep inside her.

    Upon recovering our wits, she will normally pull up, letting my cum run back over my cock and balls, giggling as she does so. However, on this particular occasion, knowing my weakness for visual stimulation, she stood up and squatted over my chest. With a wicked grin on her face, she pulled her glistening, wet pussy wide open with her fingers so that I could see deep inside her swollen folds. She then held that position so that I could watch my cum trickle slowly out of her beautiful pink pussy.

    It is an intense visual memory that has provided me with plenty of material for subsequent masturbatory experiences, and it continues to do so until this day!

  6. Frank~

    Thanks for sharing your story! It gave me great pleasure to see that I wasn’t the only one who masturbated to thoughts & images of their own wife. In my case, there’s one photo I took a few years ago which never fails to get me creaming my jeans at a mere glance. Vix was sat on our bed naked apart from a pair of thigh-high leather boots and perched between the legs of a couple fucking girl-on-top style. Just as the guy was about to cum, Vix grabbed hold of his cock with both hands, pulled it out of the girl’s pussy (can you say “coitus interruptus”?) and went down on him. When she re-emerged, his glistening cock still firmly in hand, Vix had this incredible Cheshire cat-like smile stretched across her face as his cum dribbled down her chin. That’s when I snapped the photo and, although I’m not looking at right now, I’ve still got a raging erection just from relating the story! So thanks, Frank, for making me feel “almost normal”…

    ~Reese! :~)

  7. I haven’t even seen the photo, but your description alone gave me an instant hard-on as well! From my perspective, masturbating to mental images of your partner has to be a sign of a fulfilling sex life. I mean, if your current partner has not given you the best orgasm you’ve ever had, get to work!

  8. Reese,
    Great blog, actually you have the GREATEST blog in big boob history!! The question of the greatest orgasm ever is certainly worthy of discussion. For me I can say they were all very good and some of them were GREAT. The most spine tingling cums are in the pussy as nothing can emulate the feeling of a good moist HOT pussy but SOME of the great ones have a visual attachment such as cumming on tits, cumming on butt, cumming on lips, neck and of course the hand job. Nothing like blowing a wad on your favorite lover. One of my favorites goes back to my college days some thirty one years ago as my and my girlfriend were just stuck on each other often engaging in sex three times before lunch time and yes I did actually go to class on occasion. She had a nice healthy pair of 36DD’s that were both pliable and firm at the same time. She had a oral thing for me but usually would finish me off on her breasts as she knew my craziness for cumming on her tits and she wasn’t too fond of swallowing my healthy loads. One time in the throes of a passionate boob fuck I kept riding higher and higher up on her torso and she was skillfully and I mean skillfully (women can do such wonderful things to us men with their bodies) massaging my cock between her fine tits that were topped by big areoleas and half inch nubby nipples so the visual was just overwhelming!!! Well the passion and friction got the best of me and right at the peak of a orgasm I shoved my cock deep into her tit crack and exploded …… or so I thought until I felt this incredible sucking sensation. What had happened in the throes of my orgasm I actually shoved my cock into my lover’s mouth and although she wasn’t always keen on swallowing she hungrily sucked every drop of cum out of my cock while looking up and smiling at me!!! That was a great one!! I’ve had a few others like that but don’t want to take up all your blog space. I recently took on a lover with 46EE’s and have had some great boob action with her but she also gave me the best combination hand job/tit fuck ever and she’s got a great pussy but I love to cumm on big tits

  9. My best orgasm is a fairly mundane story compared to the above (oddly for me, but I digress). Was simple missionary style vaginal sex. The kicker as to what made it a great orgasm though was that my then girlfriend came at the same time. It’s a very difficult thing to achieve, and not something either of us ever deliberately set out for, but let me just say, any orgasm is made better when the pussy you’re cumming in is cumming at the same time.

  10. What a dilemma. I couldn’t name ONE specific orgasm but over huge breasts is for some reason just “awesome”. I think I’ve only had 3 girlfriends with large enough breasts to make these my best memories but for the same reason I voted “tit job”.

    I do sometimes wonder what women get out of this but from my experience they seem to love it?

  11. Buntl1, thanks for sharing such great memories. Perhaps the answer is that the myriad permutations of orgasmic experiences is precisely what makes it so memorable!

    Georgio, although less than a third have voted for vaginal sex, there is another way of looking at this result. That is, it is actually very interesting that vaginal sex is rated first at this point, ahead of the blowjob which is often venerated as the ultimate male ejaculatory experience. This may well reflect that vaginal sex is for most of us the most intimate of sexual encounters.

    It is equally interesting though that, considering the audience at which this poll is directed, titfucks come a distant third. Does this mean that the ultimate for us boob-obsessed individuals is for our wives and girlfriends to ride us to orgasm, her boobs bouncing and swaying in front of your face as you cum inside her uncontrollably?

  12. “Does this mean that the ultimate for us boob-obsessed individuals is for our wives and girlfriends to ride us to orgasm, her boobs bouncing and swaying in front of your face as you cum inside her uncontrollably?”

    Could be that people have had more intense orgasms from other, perhaps more intimate methods? Love does play a part in orgasm enjoyment after all.

    Or maybe not everyone here’s been lucky enough to have found someone with boobs big enough to use for titfucking. I know I haven’t… *sigh*

  13. oh yes, Kelly Madison! What doesn’t she do? Best slut in porn, she does a great video with equally busty Sara Stone somewhere too.

  14. Well Surplusexistance, I know you aren’t the only one. I myself voted for blow job, because there was this one time back quite a few years when I was in High School. I had been crushing on this girl for quite some time and then I bumped into her when she was working her new job at a local restaurant. I got to chatting with her, and invited her over after she got off work. She came over to my place and we got to talking. She asked me if I would take her for a walk in the woods behind my house. We headed out and walked quite a ways from home. Then she told me that she always liked me and proceeded to pull my pants down right there in the trees. I had only had two other girls give head to me before, and a few after this particular experience. But none have ever gotten me to an orgasm with their mouth alone. Well she got down on her knees and deepthroated me on the spot. I finally got my chance to play with her boobs, which I would put on the upward side of a DD maybe larger. It took her less than 5 minutes to bring me to the most intense orgasm of my life. She sucked my dick and eagerly swallowed my entire load. This left me weak in the knees. I had to sit down before the walk back cause my legs were like spaghetti. And After I took her back home I told her that she should come back so I could return the favor. I never heard from her again and found out later that she had gotten married not more than a week after out little ‘outing’ in the woods. It has never been surpassed as one of my best High School memories.

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