Hope your day has been well
06:19:48
do you have any favorite pet names or things you like to be called when i praise you?
06:19:54
and my dad has been well, thank you :)
06:20:09
Not particularly but I enjoy praise
06:20:22
Would you like me to call you anything? Or stick to Gwen?
06:21:10
any special kinks and/or limits outside those in your profile?
06:21:14
I will use your safewords yellow/red
06:21:49
I'll let you no if it's to much
06:22:00
Once we begin, any combination of Miss/Mistress and Gwen/Gwendolyn is acceptable.
06:22:18
sounds good Miss Gwendolyn
06:22:52
We will see if I can impress you as much tonight as I did when I rescued you from denial
06:23:49
Alright, anything else before we begin?
06:24:48
I don't think so. I have a water. Towel is down. I'm ready to make a mess and of course impress
06:25:27
Excellent, and are you naked yet?
06:25:58
Still clothed. Shirt, shorts, and boxer briefs ( A nice hugging pair. Some one may have thought they were getting lucky tonight. )
06:27:16
Well then, let's get those off, shall we?
06:27:56
Yes nice and naked for you
06:28:13
and by the end of tonight, I hope to have you feeling more than just lucky ;)
06:28:26
I'm sure you're already quite eager, but let's get you warmed up anyway.
06:31:00
I am and i think you know what I really want to touch. Getting hard just thinking about it
06:31:41
nipple are nice and hard for you Miss Gwendolyn
06:32:19
Even your title change excites me
06:34:57
good, a promise of what's to cum ;)
06:35:44
Mmm I can't see what kind of record you can make
06:36:12
Not hard. To get hard hehe. May already be there
06:36:49
now, I've done a little research in preparation for this. It may be easier for you to achieve multiple orgasms if the first ones are ruined. Are you alright with that or would you like to try having multiple full orgasms?
06:39:47
You aren't wrong but after being denied I don't want to ruin it. I would rather full. Harder to achieve but it will feel so much better
06:40:55
Such a waste of a built up orgasm to ruin it
06:41:19
of course, and we can always stop after the first one at any point if it gets to be too much, or if you just don't want to continue, or any other reason
06:42:40
let's give those nipples a bit more attention
06:43:20
My cock is getting jealous of my nipples
06:44:33
omg this is agony, I want to touch so bad
06:44:54
Your not going to make this easy for me are you?
06:46:40
tease your legs, get as close as you like up your thighs, but no touching yet
06:47:08
Yes Miss Gwendolyn
06:47:19
So hard and aching to be touched
06:48:03
let me get myself a little more comfortable ;)
06:48:14
I'm a slut Miss Gwendolyn and I want to cum so bad. I want to make a mess for you
06:49:24
I'm eager for you to. I wonder if we can get you to cum until there's none left in your balls.
06:51:35
Mmm would that impress you
06:52:12
it would very much
06:52:33
My balls are very full. There is a lot to empty
06:52:59
is your cock already leaking?
06:53:53
there we go, let me just get these off too
06:54:26
Not yet but so hard and needy
06:54:38
ahhh please let me touch
06:55:34
there we go, that's a good boy
06:55:49
i was beginning to wonder when you'd ask ;P
06:56:16
Can't show weakness to early 😉 haha
06:56:53
just a little light touching first
06:57:36
Mmm yes Miss Gwendolyn
06:57:47
just to keep in mind for when you start leaking ;)
06:58:54
Mmm Yes Miss Gwendolyn. I'm sure my cock won't be able to hide its neediness much longer
06:59:43
have you ever swallowed your own cum before, I see about a self facial on your profile, but did you eat it up too?
07:01:01
I didn't. I try to avoid it but you may be able to convince me
07:02:12
I've definitely tasted it but no if I have ever taken a full load to the mouth
07:02:34
good to know, thank you :)
07:03:22
nice slow strokes
07:04:04
Can I keep stroking? Please?
07:04:34
of course you can
07:04:50
but keep it nice and slow still
07:05:15
Yes Miss Gwendolyn. Thank You
07:05:32
you're very welcome
07:05:59
Feels so good to touch
07:07:00
i wonder what all that build up and frustration tastes like
07:07:13
I think you have an idea 😉
07:07:39
I wish i could taste your precum for myself to find out
07:09:16
It's just hanging on the tit, yours for the taking
07:09:44
you'll have to describe it for me
07:10:20
One bead of translucent precum. Rubbing it into the slit of my cockhead and spreading it outwards
07:11:13
no no, the taste, describe the taste for me ;)
07:11:54
just a quick little lick
07:12:03
Kind of bland, maybe a tiny little bit of sweetness or saltiness. Not really sure how to explain it
07:13:02
that's perfectly alright, you're a very good boy for me
07:13:35
get those hands nice and slick
07:15:13
MMm nice and slippery. Feels soooo good
07:15:42
gliding up and down as you stroke your needy cock
07:15:49
jerk a little faster
07:16:30
mmm Yes Miss Gwendolyn
07:16:41
nice twisting action to my strokes
07:18:03
just like the gif
07:19:20
feels so good both hands twisting
07:19:35
mmmm feel my hands teasing it as well
07:21:06
mmm may I please edge to your hands?
07:21:25
good boy, keep count for me
07:23:03
Yes Miss Gwendolyn
07:23:15
Small bead of precum on my finger
07:23:59
do you have a shotglass available?
07:24:42
Done, I can taste it mixed with a bit of lube
07:24:49
i wonder if we can make it overflow with all the cumming i plan for you to do
07:26:04
back with the glass
07:26:05
and give me another edge
07:28:03
Mmm I want to edge again
07:29:46
yeah? do my slim fingers feel nice squeezing and stroking your cock?
07:30:07
I actually used to play the Violin, so I learned to become quite good at using my fingers. ;)
07:31:07
Making sweet music? Or playing sweet music?
07:32:02
I've tried the former on occasion, but I was always better at playing than writing. :P
07:33:14
can you get your legs over your head?
07:33:52
Will be hard to type though
07:34:18
I shouldn't say probably. I can do it haha
07:34:34
good boy, it'll just be for this next edge
07:34:54
just edge really hard
07:35:15
if you go over without permission, it all ends up on your face
07:35:49
Done. Nice hard edge, cock stiff and pointing at my face
07:36:13
does it make you nervous to be so close while your cock is aimed straight at your face?
07:37:05
a little thrill at the danger? ;)
07:37:24
A little. The edge felt different as did stroking with my legs above my head
07:37:46
well, you may stop holding the position for now
07:38:06
I'm a sucker for risk / reward. Emphasis on the the reward
07:38:37
give me a normal edge for now
07:38:52
perhaps we'll do a little risky game
07:39:31
would you like that?
07:39:51
Hehe yes. Is there a reward?
07:40:05
i don't know, it's just a thought at this point
07:41:12
All good things start with a thought
07:41:29
perhaps another time when I've fleshed it out
07:41:59
i have other plans for you tonight
07:42:09
I happy to be in your hands
07:42:25
such a good, obedient boy <3
07:43:15
it makes me very happy
07:43:36
I hope to make you happy by filling this glass
07:44:31
ahh yes I love it
07:46:18
please? please what?
07:50:41
please keep holding?
07:50:51
yes, you may stop holding ;P
07:51:13
how are you feeling?
07:53:48
Horny, needy, want more, want to edge, want to cum!
07:54:13
greedy for pleasure
07:54:20
hmm, calm down just a bit, catch your breath
07:55:03
Yes Miss Gwendolyn. Thank you
07:55:19
mmmm i wish i was there, i bet it would taste so good
07:57:21
I can picture your tongue gliding across my cock head
07:57:38
licking up the mess you're making
07:58:07
alright, back to the edge :D
07:58:27
the edges are coming so fast now
07:59:43
good, i want you desperate
08:01:44
My cock is twitching so much
08:02:58
then let's edge it again :D
08:03:24
i hope you have lots of water
08:03:56
I may have to get some more
08:04:06
I'll be right back
08:04:21
back hydrated and ready for more
08:05:14
you're doing so well :)
08:08:09
ignore the loser part of the caption, you're a wonderful, sweet, good boy <3
08:09:01
would you like another risky edge?
08:09:50
MMm Just for you Gwen
08:10:13
Such a strong close edge for you
08:11:53
so good for me <3
08:12:46
your cock must be so desperate
08:14:39
so close to cumming
08:14:56
I want it so bad
08:15:04
Please Miss Gwendolyn may I cum?
08:15:45
I'll count you down
08:17:10
straight into the glass
08:20:41
oh fuck yes that was good
08:21:19
A lot of cum in this glass
08:21:39
how full is it? :D
08:22:15
Hmm around an inch / inch and half up the glass
08:23:00
still feeling that post cum glow, so nice
08:23:28
hit continue when you're ready
08:24:09
Mm still basking in it a little
08:24:45
such a good boy, you deserve it
08:25:01
just a little tease under the head
08:25:53
nothing too intense yet
08:26:05
semi soft just teasing, gently touching
08:26:10
good boy, we'll start by seeing if we can get you nice and worked up again
08:26:51
you're doing so so good <3
08:27:12
i want to clean up any excess with my mouth
08:29:13
Mm soft tongue against my sensitive cockhead
08:29:30
get you nice and ready for your next orgasm
08:29:43
make sure you've had some water, you'll need all the fluids you can get ;)
08:30:39
I had a nice drink
08:30:56
close to hard again. May I stroke?
08:31:43
Denial will do that to me
08:32:33
and probably all the teasing you just did haha
08:32:52
let's let it build a little more first
08:32:54
i bet your nipples miss the attention from earlier
08:33:15
There not the jealous type. they don't mind sharing
08:34:05
give them some anyway
08:35:20
Of course Miss Gwendolyn
08:35:31
good boy, here's a reward ;)
08:36:12
let me feel it up
08:37:39
I'm so greedy for pleasure
08:38:50
feels good to stroke
08:38:55
make sure you're nice and lubed up still
08:39:39
little extra lube never hurt
08:40:26
hand gliding up and down
08:41:18
do you want to edge?
08:43:18
yes but im not that close yet
08:43:40
of course, we'll get there soon enough
08:44:07
I want to stroke again
08:45:03
alright, nice full strokes for me
08:45:54
you're very welcome
08:47:16
I'm closer but I'm kind of stuck on the edge of the edge if that makes sense. Feel close but far away
08:48:38
that's perfectly alright, we have plenty of time :)
08:49:29
such a teasing feel being close to the edge but not able to get there
08:52:13
mmm just imagine if there was a way to trap you like that forever, that could open up whole worlds of fun ;)
08:53:14
I bet you would enjoy the moans that come out of my mouth as I try to decide if I should beg for more or less
08:54:02
oh i definitely would
08:54:23
you'd be allowed to cum and I'd keep going until you begged me to stop
08:55:10
and I'd say "but you haven't even cum. are you sure you want me to stop?"
08:55:47
I wouldn't give in so easily. You would have to earn those words as you milk me dry
08:56:37
maybe i should try to learn how to give someone a hypnotic orgasm block
08:57:52
scary but exciting
08:58:33
have some one melt at your words
08:58:50
and I'd make them think it's possible for them to, so they get so confused when they can't quite get there
08:59:01
that would be so teasingly cruel
08:59:27
and of course I'd feign confusion too "What's the matter? Don't you want to cum?"
09:00:36
I edged, I think its going to be harder to get back there
09:01:09
don't edge to this action, in just keeping the site count consistent
09:01:32
but I'm very proud of you for reaching the edge
09:02:08
what helped you get there?
09:02:19
Your hypno denial scenario definitely helped
09:03:17
being so cruelly denied and unable to stop it
09:03:38
mmm you like the thought of being so helpless
09:04:16
Mmm yes, horny and desperate, vulnerable to your orders
09:05:01
getting "permission" from me but deep down, I've stolen your body's ability to cum
09:05:15
that would be a confusing moment
09:05:43
i'd pretend like i don't understand
09:06:04
Panic sets in as I plead for you to help
09:06:25
and tell you that you must really just love denial
09:06:35
as I try to cum again
09:06:37
I whimper knowing it is true but still wanting to cum so bad
09:07:06
I'd pump your cock hard and "beg" you to cum on my face, while knowing perfectly well you can't
09:07:56
My hips would thrust and my body would tense but nothing
09:08:24
all I want to do is cum on that pretty face of yours
09:08:47
"I don't understand, if you don't want to cum for me just say so"
09:09:19
I want to cum! So bad!
09:10:08
I feel the need build every time I try but nothing happens
09:10:21
mmm that was a good edge
09:11:01
"if you can't cum when i tell you to, maybe I should just lock that thing in a cage"
09:11:17
whimpers No not that. I can cum. Give me another chance
09:11:43
pumping you and teasing you "oh please give me that big load, i want it so much"
09:13:31
please I want to cum again
09:14:06
I'm ready to cum
09:14:15
i want a few more edges, just to make sure ;)
09:14:49
Yes Miss Gwendolyn
09:14:58
is it getting easy to reach the edge again?
09:15:37
getting desperate again?
09:16:26
please make me blow
09:17:47
empty these balls
09:17:50
maybe we should just end with denial, leave you nice and needy just like your were when we started ;P
09:18:11
I don't believe you want that
09:18:38
And I don't want that either
09:18:48
true, i don't want to deny you right now, but i do want more edges ;)
09:19:31
uh oh, i don't know, we might have to put your count back down to 25
09:20:29
what do you think
09:20:35
i was about to say i might let you cum at 50 edges
09:20:53
and then i saw your typo ;)
09:21:05
but I've been so good. You don't want to punish me
09:21:33
I'll be nice, we won't lower the count XD
09:22:01
i was just teasing
09:22:11
but if you do it again, we will
09:22:52
ah but you got my mind spinning
09:23:05
just how i want you
09:23:33
a nice weak mind, vulnerable to my commands
09:24:02
just don't secretly block any orgasms.... please
09:24:29
should i sneak a little orgasm block deep inside? ;P
09:24:31
had the same thought at the same time
09:24:50
it's oh so tempting
09:25:22
you've given me so many ideas for future sessions
09:25:43
If I get a vote. I disagree haha
09:25:44
You can't take away the orgasms I love so much
09:26:39
you don't, but lucky for you I'm still sticking to my plan. it's a good plan and i don't want to throw it off track ;)
09:26:49
stick to the plan
09:27:28
and i can, i very much can, but I'm very nice and won't steal away your orgasms
09:27:41
I hate that, that turns me on so much
09:28:13
and it'll turn you on that whenever you play with me or message me, i might decide to steal them
09:29:26
you'll never know if today will be the day i do it
09:30:12
Truly a woman to behold or fear. Haven't decided yet 😉
09:30:29
both, both is good
09:30:47
the faster you get to 50 the faster i might let you cum
09:32:30
but careful not to go too fast, don't want any accidents
09:33:10
stop edging for now
09:33:56
only when i tell you to
09:34:06
Yes Miss Gwendolyn
09:34:22
let's give your nipples some more attention XD
09:34:48
Stupid jealous nipples
09:34:52
if you go over you have to ruin it
09:36:20
so DON'T go over
09:36:33
how do you feel?
09:37:11
Heart racing, desperate to cum
09:37:26
that was intense, I'm sure, but you did so very well
09:37:36
1 more edge? so close?
09:38:18
one more edge. soon, but not yet
09:39:01
please miss Gwendolyn
09:39:13
edge me! let me cum
09:39:17
i want you to hold this one
09:41:50
pick an action while you hold
09:42:09
do you want to cum?
09:42:51
i want you to do something for me before i let you cum
09:43:47
i want you to pour the contents into your mouth while you hold the edge for me
09:45:05
hold it in your mouth
09:45:48
cum with your cum in your mouth
09:46:47
into the shotglass again
09:46:54
ah I came in the glass
09:47:41
you may now swallow
09:47:53
holy that was intense
09:48:10
not going to lie, tasted terrible
09:48:32
i know it was intense, I'm so proud of you for doing it for me <3
09:48:42
some one should tell my past self to eat more pineapple
09:48:47
You have no idea how close to going over the edge I was on that hold
09:49:17
at multiple times
09:49:33
you did so perfectly
09:49:38
such a good, wonderful, obedient boy for me :)
09:50:23
still catching my breathe haha
09:51:19
take your time, that was intense and you were amazing
09:51:59
mmm post cum bliss
09:52:52
now, once you've caught your breath, would you like to try to work up another orgasm? I won't make you eat your cum if you don't want to.
09:53:42
Give me 5 min. Water break and I'll see if my body can handle it
09:54:43
good, drink some water, your body will definitely need that about now :)
09:55:55
i don't want to push you to more than you can handle. I'm already amazed and super happy you were able to give me two orgasms already. <3
09:57:16
and both full ones at that :D
09:58:52
For sure. 3 just seems like a nice number. I want to do 3. If I will be able to that is another story
10:00:44
alright, just please please please promise to let me know immediately if it even starts to feel like too much
10:01:57
I'm not afraid to say enough is enough
10:02:18
How you hanging in there? We have been at this for a while. You taking the mandatory drink breaks?
10:03:06
yes, though i haven't been expending nearly as much fluid as you XD
10:03:54
haha true. still energy involved
10:04:21
indeed, and maybe a bit of rubbing because you're really hot doing this ;)
10:05:12
Mmm good. Partly why I want to push for 1 more orgasm. I think it would drive you wild
10:06:46
hit continue, I'm going to update the room description
10:07:00
accurate description haha
10:11:41
I'm glad this is public, I want everyone to know how amazing you've been for me. :)
10:13:01
Well I suppose this is as good of a time as any. Shall we start the attempt?
10:13:16
Luckily the image of your mouth wrapped around my cock is still so hot
10:15:08
so that other load in the shotglass, would you be okay if i try to convince you to eat it at some point again?
10:15:53
I'm semi hard feeling my cock come back to life in your mouth
10:16:10
I would prefer not to but if it will send you over the edge and make you cum I might be convinced
10:16:50
it was really hot the first time, and i hope you'll be more willing to during some edging, but i want to make sure doing that is okay before i get you edge drunk again
10:18:15
Haha I did it once. It's not something I enjoy but if you like it I can be convinced
10:19:57
personally I would rather cover you in cum 😉
10:20:27
i would also rather you cover me in cum
10:20:57
I'm such a huge cumslut you have no idea
10:21:15
i want to be absolutely drenched
10:21:40
Just imagine 2 big loads covering you and 1 more to cum
10:21:49
It's no soft dribble either my cock sprays cum
10:22:48
you would feel the pressure as it hits you spurt after spurt
10:23:00
fuck i want that so much
10:23:25
Mmm nice and hard now picturing you covered in cum
10:23:55
bobbing my messy, cum-covered face up and down as i suck your cock for more
10:25:00
mmm yes so greedy for cum. Milk this nice hard cock
10:25:42
Where do you want this last load? On your pretty face?
10:26:36
i want it all over my body, and then i want you to lick some up and push it into my mouth with a kiss
10:26:57
on my face, on my body, everywhere
10:27:18
Such a big mess to clean up. My tongue tracing up your stomach to your chest scooping up cum along the way. I push my body against yours and passionately kiss you push my cum covered tongue into your mouth
10:28:44
Mmm so sensitive
10:30:22
You know the problem with you becoming addicted to my cum? You will never be able to use your hypno orgasm block haha
10:31:27
oh, I'll just make sure to milk you every day, multiple times per day, and get a bunch of saved cum. then, when you're used to having so many orgasms all the time, you'll suddenly be cut off, unable to at all ;)
10:33:02
oh wow! Scary thought
10:33:34
remind me to stay on your good side
10:34:19
I'm a cumslut but I'm also a sadist
10:34:23
ooh, or I'll constantly milk you until you beg for me to put in the block ;)
10:35:23
I wonder which one would make me beg more?
10:36:00
me too, only one way to find out, right? ;P
10:37:13
haha lets leave that experiment for another night
10:37:49
indeed, but i hope the thought of it gets you nice and worked up
10:38:26
should we go to 100 edges this time?
10:39:13
that seems like a nice round number to me ;P
10:39:31
odd numbers can be good
10:39:42
oops, wrong one XD
10:40:05
is it weird that I fell for that gif
10:40:16
and pick an action
10:42:49
after two orgasms, i can forgive that
10:43:22
we'll just do some regular edging for a bit
10:43:49
how are you balls feeling?
10:45:31
They feel alright. My cock feels it more
10:45:51
they've been really put to work producing all this cum for me
10:46:56
how much is in the shotglass?
10:47:17
honestly it's probably roughly the same as the last one, maybe a little less but not by much
10:47:57
my mouth is actually watering right now XD
10:48:21
Some one is Jealous
10:49:36
yeah, part of the reason I'd want you to eat it, be a shame to let it go to waste
10:50:36
I'll eat it if you let me cum right now
10:51:03
and also maybe if I keep making you orgasm while you have your own load in your mouth, i can condition you to associate eating cum with pleasure ;)
10:51:52
hmm, so you want to cum right now?
10:53:54
it is getting difficult to get to the edge over and over
10:54:19
alright, take your hands off for a moment
10:54:35
yes Miss Gwendolyn
10:54:51
if you can cum hands free, you may, or we can go to 69 edges
10:55:26
I wish I could say I just came no hands
10:55:35
show off my unknown talent
10:55:56
is resisting cumming (60% chance of cum) => Came!
10:56:05
we'll work on that some other time
10:56:31
didn't let me choose otherwise
10:56:32
you're doing so well, just a few more edges and you can have orgasm number 3
10:58:19
it feels so far away
11:01:03
fuck i want to suck the cum from your balls so much
11:01:34
Please. Please let me cum
11:01:52
make it feel like I'm sucking out your soul as i drain your balls
11:02:33
oh it already does feel like that
11:03:08
XD i thought that was a put on gloves for me
11:03:20
good boy, you can make it
11:04:28
Please let me cum!
11:05:54
hold it until the timer ends
11:08:40
how do you feel?
11:09:17
I'm struggling, this is difficult
11:09:42
one more time and hold it
11:10:04
beg me to deny you ;)
11:11:53
please deny me aaaaa
11:12:30
that orgasm felt both good and bad at the same time
11:14:11
you did such a good job, that must have been a real mundfuck, but i hope it made it even better when i actually let you cum
11:15:00
it was relief and release
11:15:25
that last round was tough
11:15:37
You will be happy to know cum still spewed out, I think enough to cover that face of yours
11:16:52
i love the thought of that <3
11:18:35
Would it be alright for me to share the log of this with Red?
11:20:13
That was quite the experience
11:20:14
Thank you Gwen, you were amazing. It was quite a time. Fun was had. I think you effectively drained me and I am ready to get some sleep
11:33:11
I can't say it enough. You are amazing and you did such a good job for me. Get a good sleep. I look forward to your next visit. <3
11:34:36
Thanks, Until next time
11:34:59
