Randomized Faceless SEX DIARY August 201
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My Dirty Week, August Long Weekend 2019 free porn video
My dirty week - this August long weekend 2019
I am going to be alone for one week this August! My family is all away and I will be all alone.
I can’t believe what an awesome opportunity this is going for me to indulge in all the behaviours that I spend hours dreaming about. But I have so many fantasies how do I fit them all into just one week over the long weekend. It is kind of like trying to fit my cock into these far too small panties I have just slipped on here at the office today. I stole them from my niece. Cotton low cut bikinis, white with black and pink polk-a-dots and the classic Calvin Klein elastic waist band. They do not fit me well, but when I think of them caressing the ass of my niece, it becomes almost impossible to focus on work.
I am so excited and nervous about my week and the problem of fitting everything in that I am tackling it the way I take on most challenges, making a list and using that to make a plan.
To begin, you should know that I love to wear women’s lingerie, as you can see from my profile pics. I am reluctant to call myself a true Crossdresser because I am just not good looking enough! No amount of make up or properly sized lingerie can cover up my slightly oversized shape or hairy body. I do my best to keep the hair trim and wax my back BUT I will never be the smooth hairless sissy trap I wish I could be. Regardless, I love to dress up and show off.
However, moving on, that does not stop me from having fun! I love to do wild and kinky sexy things. The list of my accomplishments in the field of perversion is long and lovely, like my cock! Lol.
So here is the list to get me started of all the dirty nasty naughty things I can think of doing, in no special order, and some comments on them. I would love your feedback and any suggestion you may have;
• Club M4 - Have you ever been? Really cool sex/swingers club in South Etobicoke, a suburb of Toronto. I have been twice, to the Tranny nights, and I LOVE IT! Definitely planning on the Tuesday night party there BUT, will the Tuesday after a holiday Monday be any good? Will all the sexy ladies be away for the short work week or will MORE be there because they are on holiday. If anyone has any advice here, I would love to hear it.
I plan on going multiple times if possible during my week. Tuesday for sure but also Thursday cougar night looks fun and Sundays. That is the great part about having multiple fetishes, you can always have a good time regardless of the party theme. I just love licking and sucking and cuming!
• Strip clubs – not as many as there used to be. I am considering an evening visit, but really think day time is better for that week, keep my nights free. Maybe have lunch at one while at work. When I go I like to wear some lingerie under my manly clothes. Then get a private dance and shock the girls by telling them, then showing them the sexy hot pink silk thong I am wearing. But I am a little on the cheap side and those dancers are so good a pulling money out of you. For what I spend there I could have a good time with a Pro.
• Nude Beaches – I know of 3. I love being naked in public and nude beaches are about the safest place to strut your stuff. I know full well however, I am one of those people that most regular people prefer not to see naked. Lol! Also, I have to spend a lot of my time “fluffing” the cock as I am definitely a grower not a show’er. When I come out of the nice cool Lake, my little turtle is almost completely gone.
o Hanalan Point – very popular, almost too busy but fun.
o Port Burwell – 3 hours outside of Toronto BUT the MOST fun. Lots of straight women/couples to look at and lots of playing going on.
o East Point Park – close to home on the East side of Toronto BUT hard to access at the bottom of the bluffs. So you don’t see a lot of women there but the men are all very healthy. Hard for out of shape people to get there.
• AVS – easy to find someone to suck you.
• Public Fem Dressing
o Home – as much as possible naturally – nighties to bed even
o Office – I will “underdress all week” but may stay late then change into full ladies wear and drive home!
o In car – drive home, drive the neighbourhood
o At night – walking around my neighbourhood at night fully dressed! I love exhibitionism.
• Massage Parlours – I would say I have an amazing time once every 6 visits, just ok the rest of the time. You get what you pay for, mostly. Fun to see their reaction to me dressed up!
• Professional sex workers – straight women – 50-50 on how much fun. I love the girls who get into my scene and let me lick them.
• Professional sex workers – tranny! I love these women. Never have I had a bad time with one, but I have only been with 3. If I am sucking cock it is shecock! Well and sometimes a good CD. OK sometimes any cock will do. But I love trannies!
• Squirt – cruise spots and hook ups. As above, when you just need cock. I try to find guys who have the same lingerie fetish or are actual CD’s but it is not easy.
• Online chat rooms – really hard to find fun people on here. I use Chat random. Anyone have any other ideas.
• Nude full time at home – when I am not fully dressed, I intend to be fully nude. Curtains and doors open of course, there for anyone who is looking to see. Exhibitionism.
• Nudist resorts – Only one of two things on this list I have not already done but am curious about. Bare Oaks is close to home. As above, I love being naked. But I have never been to one and from what I can see it is a very non-sexual vibe. I mean families go there. Am I right?
• Shopping for lingerie – I regularly go to sex shops that have lingerie to sell as well as department stores and malls and try to get the attendants to let me try on the lingerie! I have been successful lately. The hot pink one piece body suit in my profile pics came form one of these outings. It is such a rush when you finally tell the sales girl that you are looking to try on the lingerie yourself! They always take it well, and either tell you there is a policy against it or they say go right ahead. The two best times I had were recent. First, at a mall store called Torrid. When I asked the sales lady if I could try on some panties she smiled and said “Oh, this is going to be fun”. She was very professional after that, put me in a change room and started to bring me super sexy outfits to try on. But that was it. And it happens this way most often, these girls need their commission and I usually buy something. The other most sexy time was at a sexy store in Barrie Ontario. I was on the look out for a new body suit and the attendant had no problem with me trying things on but, she said, if it has a closed crotch, she had to watch me try it on! Are you k**ding me? That is the dream. I have no idea why she drew the line there, but I was not arguing. I think I stammered out something like, “no problem here” while trying not to seem too excited. The hardest part from there on was trying to keep my ever-growing rock-hard cock inside the sheer green panties I was already wearing as I tried on body suits in front of her! She basically saw all that I have to offer. I still use that event as jerk off material.
• Transformation services – my best chance to see if I could look like the sexy little whore I so want to be. I have heard they do great work making even hairy dudes like me look ultra fem. Take a Walk on the Wild Side is here in Toronto, if they are still open. This is the second thing on this list that I have not already done but think it would be awesome!
• Swing shift – it is an AVS but worth calling out as it is the best around. 3 group rooms and I had one of the most amazing experiences there. It really warrants a story unto itself but what happened was this. I was in a group room with about 12 guys watching straight porn when in walks an ultra manly guy, sk**oo jacket, work boots, buzz cut. I leave for a bit, jerk off a feminine looking guy in the “gay” room then come back. The Ultra male has now changed into a mini dress, heels and long gloves. No wig or makeup. And he is getting fucked up the ass by one ugly dude. When the dude is done the CD walks over to me, I happened to have me dick out at this point openly jerking in a room of more than a dozen now, and he kisses me. His breath was horrible, I figured out later he must have had dick sucking breath because that is what he did to me. When I was ready to blow I told him and he asked me to cum on his face. Never one to disappoint I did. It was awesome. I zipped up and got out but I really should have stayed. I hear this stuff goes on regularly at this place so a return trip should be on the plan.
• Club 120 – a gay club most of the time I believe, in downtown Toronto but on Thursday’s they do a tranny night. Goodhandy’s they call it in honour of the founder Mandy Goodhandy, a transsexual pioneer in Toronto. I went once, it was pretty quite just a few gurls there but there was a VIP lounge and I can only imagine and hope what goes on there. The one sexy girl I talked to was an amazing petite Asian. It cost to get in, more to get a wristband for the VIP lounge and I have a feeling you have to tip the gurls. See my note about strip clubs. It was ok, but definitely worthy of a return visit.
That’s about everything I can think of.
As far as AVS, Swing Shift and Squirt hook ups, I always do those, or want to do those fully dressed! However, doing so I feel that puts pressure on you to be a bottom, and I am virgin back there and don’t have plans to bottom. They see a guy walking around in wig, makeup, lace bra and panties set with garters, stockings and high heels and I get it. Even as non-passible as I am they think I should be a submissive fem bottom.
The other thing is, the most pleasurable thing for me is to cum by my own hand. I love jerking off. No one can make you feel as good as yourself. But you don’t go to the places I want to go to jerk off. You have to be willing to play, and I am, it is great fun. But I like to pull it. So why not just stay at home, watch porn and stroke it for a week straight? For me the issue is, I need more and more different stimuli to make it fun. Sure we all start with straight porn, but after a while we are looking for something more, maybe two girls because the boys in the school yard said that was cool. After that we graduate to teacher porn or see our Sister’s or Mother’s panties and start using those to jerk off like I did. Now here I am, many years down the road and the stimuli I need (or want really) is vast and diverse. That is why I need to be out there swinging my cock around. But at the same time am very cautious about who I hook up with.
Tentative Schedule
Thursday
Drop family off at airport. As this is close to strip clubs, drop in for a quick howdy-do and dance. Show off some panties.
Stop off at Club M4 for cougar night to check that it. If it is a good time, hang out, you must be naked if you are a man there, and try to get laid.
If M4 is not that good, head over to Club 120 and find a sexy t-gurl.
Sleep in my hot pink nightie
Friday
Go to work, wear a bra and pantie set under my clothes, take my full “fag bag” of fem attire. Stay late, change into fem wear and leave work fully dressed and made up. Head over to the local Massage parlours and walk in and out on the pretense of checking the girls out. This is just really a chance for me to show off in a relatively safe space. If there happens to be one really sexy attendant who is willing to fuck my slutty ass then stay and pay.
The website says Friday nights are the best at club M4, Threesome night. So head there before 10 and see what happens!
If M4 is not great, hire a pro.
Sleep nude
Saturday
Nude beach for sure if the weather permits, but which one. I will keep an eye on Squirt to see where the action is. I will wear my niece’s (same one as whose panties I currently am leaking pre-cum into) old bikini bottoms, super small blue and white checked, side string tie once on the beach until I see naked people. I will walk around until I see some sexy action. Hopeful ladies, but most likely not.
Can’t go to Club M4 on Saturday night, no single men allowed, so maybe look for a place to cruise while fully dressed? Or find a friend somewhere??? Or get dressed up and walk around my neighbourhood.
If nothing else, arrange a meeting with a Pro tranny and suck suck suck!
Sunday
Spend the morning walking around the house naked.
Go to Walk on the Wild Side to get completely transformed!
Head up to Swing Shift, get a private room and entertain!
Monday – civic holiday, no work
Also a naked day, but maybe a long drive back to Port Burwell for a naked day there?
Tuesday
Underdressed at work again.
Club M4 for tranny night!
Wednesday – going to be tired and probably have a sorry dick but I must power through
Underdressed at work
Do the change agiain after work
Head to the local AVS??
Then that is it.
I would love to hear your thoughts, feedback and any ideas you may have!
I am going to be alone for one week this August! My family is all away and I will be all alone.
I can’t believe what an awesome opportunity this is going for me to indulge in all the behaviours that I spend hours dreaming about. But I have so many fantasies how do I fit them all into just one week over the long weekend. It is kind of like trying to fit my cock into these far too small panties I have just slipped on here at the office today. I stole them from my niece. Cotton low cut bikinis, white with black and pink polk-a-dots and the classic Calvin Klein elastic waist band. They do not fit me well, but when I think of them caressing the ass of my niece, it becomes almost impossible to focus on work.
I am so excited and nervous about my week and the problem of fitting everything in that I am tackling it the way I take on most challenges, making a list and using that to make a plan.
To begin, you should know that I love to wear women’s lingerie, as you can see from my profile pics. I am reluctant to call myself a true Crossdresser because I am just not good looking enough! No amount of make up or properly sized lingerie can cover up my slightly oversized shape or hairy body. I do my best to keep the hair trim and wax my back BUT I will never be the smooth hairless sissy trap I wish I could be. Regardless, I love to dress up and show off.
However, moving on, that does not stop me from having fun! I love to do wild and kinky sexy things. The list of my accomplishments in the field of perversion is long and lovely, like my cock! Lol.
So here is the list to get me started of all the dirty nasty naughty things I can think of doing, in no special order, and some comments on them. I would love your feedback and any suggestion you may have;
• Club M4 - Have you ever been? Really cool sex/swingers club in South Etobicoke, a suburb of Toronto. I have been twice, to the Tranny nights, and I LOVE IT! Definitely planning on the Tuesday night party there BUT, will the Tuesday after a holiday Monday be any good? Will all the sexy ladies be away for the short work week or will MORE be there because they are on holiday. If anyone has any advice here, I would love to hear it.
I plan on going multiple times if possible during my week. Tuesday for sure but also Thursday cougar night looks fun and Sundays. That is the great part about having multiple fetishes, you can always have a good time regardless of the party theme. I just love licking and sucking and cuming!
• Strip clubs – not as many as there used to be. I am considering an evening visit, but really think day time is better for that week, keep my nights free. Maybe have lunch at one while at work. When I go I like to wear some lingerie under my manly clothes. Then get a private dance and shock the girls by telling them, then showing them the sexy hot pink silk thong I am wearing. But I am a little on the cheap side and those dancers are so good a pulling money out of you. For what I spend there I could have a good time with a Pro.
• Nude Beaches – I know of 3. I love being naked in public and nude beaches are about the safest place to strut your stuff. I know full well however, I am one of those people that most regular people prefer not to see naked. Lol! Also, I have to spend a lot of my time “fluffing” the cock as I am definitely a grower not a show’er. When I come out of the nice cool Lake, my little turtle is almost completely gone.
o Hanalan Point – very popular, almost too busy but fun.
o Port Burwell – 3 hours outside of Toronto BUT the MOST fun. Lots of straight women/couples to look at and lots of playing going on.
o East Point Park – close to home on the East side of Toronto BUT hard to access at the bottom of the bluffs. So you don’t see a lot of women there but the men are all very healthy. Hard for out of shape people to get there.
• AVS – easy to find someone to suck you.
• Public Fem Dressing
o Home – as much as possible naturally – nighties to bed even
o Office – I will “underdress all week” but may stay late then change into full ladies wear and drive home!
o In car – drive home, drive the neighbourhood
o At night – walking around my neighbourhood at night fully dressed! I love exhibitionism.
• Massage Parlours – I would say I have an amazing time once every 6 visits, just ok the rest of the time. You get what you pay for, mostly. Fun to see their reaction to me dressed up!
• Professional sex workers – straight women – 50-50 on how much fun. I love the girls who get into my scene and let me lick them.
• Professional sex workers – tranny! I love these women. Never have I had a bad time with one, but I have only been with 3. If I am sucking cock it is shecock! Well and sometimes a good CD. OK sometimes any cock will do. But I love trannies!
• Squirt – cruise spots and hook ups. As above, when you just need cock. I try to find guys who have the same lingerie fetish or are actual CD’s but it is not easy.
• Online chat rooms – really hard to find fun people on here. I use Chat random. Anyone have any other ideas.
• Nude full time at home – when I am not fully dressed, I intend to be fully nude. Curtains and doors open of course, there for anyone who is looking to see. Exhibitionism.
• Nudist resorts – Only one of two things on this list I have not already done but am curious about. Bare Oaks is close to home. As above, I love being naked. But I have never been to one and from what I can see it is a very non-sexual vibe. I mean families go there. Am I right?
• Shopping for lingerie – I regularly go to sex shops that have lingerie to sell as well as department stores and malls and try to get the attendants to let me try on the lingerie! I have been successful lately. The hot pink one piece body suit in my profile pics came form one of these outings. It is such a rush when you finally tell the sales girl that you are looking to try on the lingerie yourself! They always take it well, and either tell you there is a policy against it or they say go right ahead. The two best times I had were recent. First, at a mall store called Torrid. When I asked the sales lady if I could try on some panties she smiled and said “Oh, this is going to be fun”. She was very professional after that, put me in a change room and started to bring me super sexy outfits to try on. But that was it. And it happens this way most often, these girls need their commission and I usually buy something. The other most sexy time was at a sexy store in Barrie Ontario. I was on the look out for a new body suit and the attendant had no problem with me trying things on but, she said, if it has a closed crotch, she had to watch me try it on! Are you k**ding me? That is the dream. I have no idea why she drew the line there, but I was not arguing. I think I stammered out something like, “no problem here” while trying not to seem too excited. The hardest part from there on was trying to keep my ever-growing rock-hard cock inside the sheer green panties I was already wearing as I tried on body suits in front of her! She basically saw all that I have to offer. I still use that event as jerk off material.
• Transformation services – my best chance to see if I could look like the sexy little whore I so want to be. I have heard they do great work making even hairy dudes like me look ultra fem. Take a Walk on the Wild Side is here in Toronto, if they are still open. This is the second thing on this list that I have not already done but think it would be awesome!
• Swing shift – it is an AVS but worth calling out as it is the best around. 3 group rooms and I had one of the most amazing experiences there. It really warrants a story unto itself but what happened was this. I was in a group room with about 12 guys watching straight porn when in walks an ultra manly guy, sk**oo jacket, work boots, buzz cut. I leave for a bit, jerk off a feminine looking guy in the “gay” room then come back. The Ultra male has now changed into a mini dress, heels and long gloves. No wig or makeup. And he is getting fucked up the ass by one ugly dude. When the dude is done the CD walks over to me, I happened to have me dick out at this point openly jerking in a room of more than a dozen now, and he kisses me. His breath was horrible, I figured out later he must have had dick sucking breath because that is what he did to me. When I was ready to blow I told him and he asked me to cum on his face. Never one to disappoint I did. It was awesome. I zipped up and got out but I really should have stayed. I hear this stuff goes on regularly at this place so a return trip should be on the plan.
• Club 120 – a gay club most of the time I believe, in downtown Toronto but on Thursday’s they do a tranny night. Goodhandy’s they call it in honour of the founder Mandy Goodhandy, a transsexual pioneer in Toronto. I went once, it was pretty quite just a few gurls there but there was a VIP lounge and I can only imagine and hope what goes on there. The one sexy girl I talked to was an amazing petite Asian. It cost to get in, more to get a wristband for the VIP lounge and I have a feeling you have to tip the gurls. See my note about strip clubs. It was ok, but definitely worthy of a return visit.
That’s about everything I can think of.
As far as AVS, Swing Shift and Squirt hook ups, I always do those, or want to do those fully dressed! However, doing so I feel that puts pressure on you to be a bottom, and I am virgin back there and don’t have plans to bottom. They see a guy walking around in wig, makeup, lace bra and panties set with garters, stockings and high heels and I get it. Even as non-passible as I am they think I should be a submissive fem bottom.
The other thing is, the most pleasurable thing for me is to cum by my own hand. I love jerking off. No one can make you feel as good as yourself. But you don’t go to the places I want to go to jerk off. You have to be willing to play, and I am, it is great fun. But I like to pull it. So why not just stay at home, watch porn and stroke it for a week straight? For me the issue is, I need more and more different stimuli to make it fun. Sure we all start with straight porn, but after a while we are looking for something more, maybe two girls because the boys in the school yard said that was cool. After that we graduate to teacher porn or see our Sister’s or Mother’s panties and start using those to jerk off like I did. Now here I am, many years down the road and the stimuli I need (or want really) is vast and diverse. That is why I need to be out there swinging my cock around. But at the same time am very cautious about who I hook up with.
Tentative Schedule
Thursday
Drop family off at airport. As this is close to strip clubs, drop in for a quick howdy-do and dance. Show off some panties.
Stop off at Club M4 for cougar night to check that it. If it is a good time, hang out, you must be naked if you are a man there, and try to get laid.
If M4 is not that good, head over to Club 120 and find a sexy t-gurl.
Sleep in my hot pink nightie
Friday
Go to work, wear a bra and pantie set under my clothes, take my full “fag bag” of fem attire. Stay late, change into fem wear and leave work fully dressed and made up. Head over to the local Massage parlours and walk in and out on the pretense of checking the girls out. This is just really a chance for me to show off in a relatively safe space. If there happens to be one really sexy attendant who is willing to fuck my slutty ass then stay and pay.
The website says Friday nights are the best at club M4, Threesome night. So head there before 10 and see what happens!
If M4 is not great, hire a pro.
Sleep nude
Saturday
Nude beach for sure if the weather permits, but which one. I will keep an eye on Squirt to see where the action is. I will wear my niece’s (same one as whose panties I currently am leaking pre-cum into) old bikini bottoms, super small blue and white checked, side string tie once on the beach until I see naked people. I will walk around until I see some sexy action. Hopeful ladies, but most likely not.
Can’t go to Club M4 on Saturday night, no single men allowed, so maybe look for a place to cruise while fully dressed? Or find a friend somewhere??? Or get dressed up and walk around my neighbourhood.
If nothing else, arrange a meeting with a Pro tranny and suck suck suck!
Sunday
Spend the morning walking around the house naked.
Go to Walk on the Wild Side to get completely transformed!
Head up to Swing Shift, get a private room and entertain!
Monday – civic holiday, no work
Also a naked day, but maybe a long drive back to Port Burwell for a naked day there?
Tuesday
Underdressed at work again.
Club M4 for tranny night!
Wednesday – going to be tired and probably have a sorry dick but I must power through
Underdressed at work
Do the change agiain after work
Head to the local AVS??
Then that is it.
I would love to hear your thoughts, feedback and any ideas you may have!
Stevie
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