The Ever Elusive Anal Sex Story...

Hi everyone, if you haven't guessed by the title, this blog will be all about anal sex and my experiences involving this exciting sex act!  I have been lucky to have this experience, but in the more recent past I find it very difficult to find a willing party.  Maybe some of my loyal readers will have some ideas of how to make this a much more common activity for me.

My first experience with anal sex came when I was 18 years old and working my first ever job in the fast food industry in the Nepean area.  I won't name the actual chain, but it's one of the top 4 chains I around town.  This is the perfect job to meet girls who are open to all sorts of things.  I found the girls in these jobs generally had values that were certainly on a different level than what my family taught me (not that I ever listened).  Don't get me wrong, I am not judging them or their families and in fact, I have made some long lasting relationships with people from this job.

Me and this very pretty girl named Chantelle, about two years younger than I struck up a relationship.

Turns out she had previously been in a couple of bad relationships.  However, she was the most loyal and devoted girlfriend I have ever had and perhaps to some extent this had been her downfall in the past, no matter how her boyfriends treated her she would not let that negatively affect her view of them.  Chantelle was a slender, blonde girl with a very cute face.  Her hair was short just above her shoulders and caressed her face.  She was small breasted but perky and had an amazingly tight ass that only a young woman could have.  The kind of girl that just fits so perfectly under your arm.  Despite her very innocent look she had a lot of interesting experiences for her age, not all of which were positive.

When our relationship progressed and we began having sex I had quizzed her about her past sexual  experiences since I did not want to push her too far too soon.  I found out that she was as equally experienced as I was and in fact, perhaps a bit more experienced.  She had tried anal sex with her previous boyfriend and she said she said that she did not love it but had no problems doing it.  I put that in the back of my head and we began having amazing sex.  I remember sneaking off to the local nature trail in the dead of night in my Dad's station wagon.  After making out in the front seat for a bit we would lay back the seats and climb into the back and continue.  

We'd always take it slow, her shirt would come off first and I would suck on her firm, perky tits, she had those perfect pink nipples, perfect circle, and erect.  While I sucked her tits I would stroke her flat stomache, my hand inching ever nearer towards her cunt.  

She would make a move to unbuckle my belt and pants and start stroking me before moving down to take me inside her mouth.  When she came back to me I would have her wiggle out of her pants, pull off her tiny panties and slowly make my way down her body stopping constantly to kiss and suckle as I made it to her waistline.  I would ease my fingers inside of her and start licking her clit.  I would taste her until I heard her begin to moan and writhe in pleasure before climbing slowly back up her stomach and pausing to play with her erect nipples before sliding my cock inside of her wet pussy.  

We would fuck for a while in the missionary position but she liked to ride me, so after a few minutes we would switch places, allowing me to squeeze her tits while she fucked me.  When I was just about ready to cum I would have her get back on her back so I could be in control while I would cum inside of her.  

I can still picture her pretty face, neck arched back, moaning sweetly as I would pump the last bit of cum into her.  Often times I would prefer to finish in her mouth or on her face.  She was always willing to please and would always do as I asked.

That was our normal routine, sometimes, naturally we would throw a little doggie style in the mix, although, it was never that easy with the roof of the car always getting in the way of my head!  

As our relationship got more serious I finally brought up wanting to try anal sex since I have never tried before.  She was more than willing and we started looking for an opportunity to give it a shot.  Since we were both living at home, and I was driving my dad's wagon at the time, it was not always convenient to plan something that would allow us to get away and have the opportunity for our first anal escapade.  Finally, we made our way to a nature trail again, however, it was not our regular spot and it was in an area with more nearby traffic, and we were not in the wagon, but rather a smaller coupe style vehicle.  We planned for a quick blow job before moving along.  

Chantelle being the sexy little girl that she was started sucking my cock, but before long I wanted more and I had pulled her up to play with her tits.  I could not resist her flat stomach and made my way down to feel her flat tummy while we necked.  The passion and urge took over and I unbuckled her belt and pants and slid my fingers inside of her.  Although, being slightly worried that someone would have the same idea or worse yet some cops coming to check up on the area I decided to have her wiggle out of her pants.  I slid over to the passenger seat and she dropped her wet pussy on my throbbing cock.  

We fucked for awhile, and while she was riding me she whispered in my ear "Do you want to try it in my ass?".  I did not hesitate and she slipped her cunt off of my cock and I struggled to put my cock in her ass.  I was not having much luck to be honest, so she took control grabbing my cock and guiding it right into her asshole.  I slid in without any trouble at all and could not believe the amazing sensation of her tight asshole on my cock.  

It was not something I had ever experienced and I had not ever experienced anything like it.  I was loving it, and loving Chantelle for sharing this with me.  We necked while I fucked her ass and squeezed her perfect tits.  It was not long before I was filling her ass with cum and moaning hard for her.  

This was not the last of my anal sex with Chantelle, far from it.  We would sort of rotate from regular sex to anal sex.  I wish I could find that in a woman again!  We had more experiences in my Dad's wagon, I remember fucking her ass at the drive-in that once existed in West Ottawa.  Just before I finished she complained that it hurt and asked me to stop, but she let me finish since I was nearly done.  

There was something distinctly erotic about fucking her and hearing her moan in pleasure in pain, something similar to when you fuck a virgin and she is loving your cock but begging for it to be over at the sametime.  We once fucked at her friends house during a house party, in the same room as another couple also fucking in the ass that night.  I will cherish my time with Chantelle for many reasons, but I would be lying if the anal sex and other daring sex stories that I have from my time with her.  If you are ever reading Chantelle, I loved you very much and thank you for everything you did for me.  

That is my story about first time anal sex and my first anal sex girlfriend.  I had planned to include several other anal sex experiences, but I fear this post will become too long and repetitive.  Therefore, I will save my other stories, perhaps for a later post.  Please leave you feedback, comments, questions, suggestions, or concerns by commenting on my blog.  I would love to hear from all of you.  If you were not a fan of the anal sex stories then let me know and I will skip the other ones I had in mind, or if you are a big fan of them... say it with a comment!

Thank you, Read again! (in my best Pakistani accent).

My new friend Sonia... Proscort?

Hello again loyal blog readers; it is always a pleasure and an honour to have the opportunity welcome and say hello to you all!  I wanted to relay a very recent experience I have had which involves the local Ottawa Escort scene.  This in a way could be a continuation of my earlier two blogs related to the telephone chat lines; a Chat Lines Part III if you will.

Not very long ago, I decided to call up a local telephone dating line and use the free time promotion that was being offered.  It is a great deal, and can be used more than once provided enough time has passed since your last use of this promotion.  Don’t let that secret get out or they may just fix it so you can only use this once!  Since it is not a cheap service to use I enjoy every free minute I have.  What was I looking for, in fact, I was open to a range of options, but mainly figured I might find a sexy woman’s voice to share some hot steamy phone sex with.  (Ladies feel free to send me your digits if you want to take me up on this offer!)  However, in my profile message I made it clear that I was open to hot chat, chance meetings, or any other unique ideas, in the hopes that some fun ladies would be interested to propose some ideas of their own.

Before too long, I was hit with a message asking me if I would like to have a get together for some adult fun.  Before I got too excited I imagined that this would be a pay for play scenario which I am not against but was hoping for some free fun since my funds were a little low at that very moment.  Sure enough, I was correct and my new friend, Sonia proposed a meeting.  She described herself as a 41 year old, petite and sexy brunette calling from the west end Ottawa area with her own place.  Her voice was feminine, smooth and inviting.  She did not sound rough, desperate, and crude as some of the women offering such services on this line.  I am not against the services that prostitutes offer, but the cleanliness and safety is always an issue with that sort of thing.  I do always find that the women on the chat lines are one step up at least.  For example, they must be well enough off to own a phone and pay a phone bill.  Ok, it is not much but it is something, perhaps there is a term for these ladies, it seems like it is something in between prostitute and escort, maybe a proscort?  Regardless, she called herself an escort...

The rates that she proposed were also quite manageable.  Despite my good feeling about this woman I was still hesitant and asked her if she had any pictures online.  She was quick to provide me with an e-mail and a social media account that indeed had some pics.

After checking out her profile I was pretty happy with what I was seeing.  As I was 7 years her junior the opportunity to be with an older woman was also appealing to me, even though this would not be my first time.  Again, I was unable to come up with the cash for this exchange at that very moment even though the rates were very low.  I jotted her number down for a rainy day and tucked it away in a safe place.

Sure enough, I found myself at work thinking about getting some action since my wife has - for good reason - not been able to make me a happy man.  Pay day had just passed and it was the perfect opportunity for a little afternoon delight.  I snuck away to a private phone and made a quick call to my fair lady Sonia.  I caught her slightly unprepared and she had to make arrangements to free up her schedule, which was fine since she had a couple of hours to do this.  We managed to agree to a lunch hour meeting at her apartment in the west end.  My cock was hard as I was talking to her in anticipation, and as I left the private phone I wondered if any of the women would notice my cock bulging out of my jeans.

When I arrived at her place, she met me in the lobby which I like since it is easy to walk away if the real deal fails to live up to the hype so to speak.  In person, I admit she was perhaps slightly less attractive than what was presented on her social media site.  However, to be fair, this was not due to a purposeful deceit, simply she was looking her very best in the photos.  She was of average height, a brunette with brown eyes.  Her make up could have been improved and a haircut and treatment may have been in order.  That said she was dressed nicely in beige pants and lug style boots, with a vest jacket over top a long sleeved red and white striped top.  As I followed her to the elevator I remarked that she was indeed petite and had a nice ass.  The quality of her tits was too hard to discern at this time due to the clothing and vest but overall, I was impressed.  Not blown away by any means but not disappointed either.  As we rode up in the elevator and walked to her apartment there was some nervous energy on both of our parts.  However, she was polite, friendly and made good conversation.  When we arrived to her unit she continued with some friendly chat for a bit and I took the lead in talking about the business end of things.  She asked me to place my gift on her kitchen table as she was under the impression that if I handed it to her this would make the transaction illegal, but if I left the money on the table this would be legit.  In fact, we were not breaking any laws since we had not officially discussed any specifics beforehand and were now discussing them in a private location; at least that is my understanding.

Following the gift left on the table, we agreed on a blowjob.  It did not take me long to get all of my clothes off, just as she was starting to peel off her layers.  My cock was erect and in fact, probably had been since stepping off the elevator.

She peeled off her vest and pulled up her shirt leaving her bra in place.  She explained that topless is fine but the bottoms must stay on since “that leads to other things”.  She started stroking my cock as I stood naked, her topless with her bra on, in front of her futon made up as a bed.  I asked her if I could remove her bra and she said that would be fine.  I reached in her bra first fondling her tits and playing gently with her nipples before reaching back and unsnapping her bra.  She was a 41 year old mother, and some of the wear and tear on her body is apparent but yet she was still quite sexy.  Her breasts obviously once large and perky were now still a great size and hanging just a bit more than they would have 10 years earlier I am sure.  But she still had very nice C-Cups with beautiful and fresh pink nipples.  We lay on the bed together and I continued to feel her tits and slowly brought my mouth to her nipples.  Playfully licking her pink nipples with my tongue and hearing her moan just a little.  Everything felt right even though, I know it’s just all wrong…  She was slim and soft, but she had obviously endured a C-section birth in the past and bared the tummy scar to prove it.  Not extremely attractive but this still did not deter me one bit.  She was making me horny and I was burning to have her mouth on my cock!

With my throbbing cock in her hand she slowly moved down my body and kissed me.  Even more blood running into my cock as she got to her knees and began sucking my cock.

She was up and down to the very bottom my cock, my head pushing against the back of her throat.

As she moved up my cock with her lips, she would follow with her hand squeezing my head.  I could easily see and play with her tits while she sucked me off.  We had agreed to just a blow job but the result had me wanting more from this unlikely temptress.  I told her that if she would rather fuck me that I would be ok with that.  A true business woman while continuing to stroke my cock she told me that she would like an additional gift.  She continued to suck on me while I considered pulling out the extra gift I still had tucked away in my pocket.  I stopped her again, and agreed to increase the gift when we were done.  She pulled out a condom and snapped it on my hard dick before drizzling it with some lube for her comfort.   She wiggled out of her pants and showed me her pussy.  Her lips hung nicely at 41 she still had a beautiful, large pink clit.  She allowed me to play with her clit and stick my fingers inside of her; she was becoming instantly wet and was ready to go.  She made her way back, straddled me, and put my cock inside of her.  She rode me with quite some good energy for a 41-year-old lady.  Her pussy was still tight and made my cock feel right at home and I continued to squeeze her tits as she fucked me with quiet moans.  Finally, I began to feel the cum rise up my shaft, and before I knew it I was exploding inside the condom and inside of Sonia.  She seemed proud of her handy work and slowly removed herself from the futon.  We got dressed, chatted a little bit more and then made our goodbyes.  I have not returned to Sonia since, but I will keep her on my list, and maybe one day in the future our paths will cross again…

I hope you enjoyed my real life experience with Ottawa Chat Lines, proscorts and my new friend Sonia.  I would appreciate your feedback so please do not be shy to leave a comment, or perhaps share an experience that you have had yourself.

Massage In Ottawa

Hi folks, today I am reminiscing about some of my past and awesome experiences with Ottawa Massage Parlours.  I really have enjoyed probably 90 percent of my massages, there were a couple where I felt I wasted my money... but you win some you lose some.

I remember my first experience in my late teens, I can not recall how I first heard of the massage parlors but when I did I could not resist and had to test it out for myself.  I recall nervously entering the non-descript building thinking that it felt a little shady.  I made my way to the particular unit listed on the sign in the foyer and entered with a bell ringing above my head to alert the massage attendants to my presence.

Shortly a woman approached and I noticed her get up from a couch at the back of the room.  She was pleasant, in her early forties I would guess.  Not exactly a stunning woman but slightly above average. She was of average height probably 5'4", with dirty blond curly hair.  She had a slender physique with probably a B-cup, tanned and lightly freckled.  She was wearing a silk robe which stopped at her mid thigh which had a way of falling on her firm ass which gave her an athletic look.

She took my payment for the massage and ushered me into a small dimly lit room with a massage table and a small ghetto blaster playing spa music.  She left me to get out of my clothes, so I slipped out of my clothes and debated do I leave my underwear on or take them off?  I decided I knew what my intent was and it would be better with my underwear off so off they came.  I was still unsure if this would be a regular massage or if it would produce a happy ending as I had heard about.  I lay down on my stomach and covered up with a towel and nervously waited for her return.  She came back into the room and began to massage my back.

I had never experienced any kind of massage at the time and it felt great, I thought she was doing an amazing job.  She started making small chat and asked me if I had ever had a massage before.  I admitted that this was my first, which she probably had guessed due to my young age and slight nervousness.  Yet she had a way of keeping me relaxed, she was gentle, relaxed and easy to talk with.  After awhile she asked me to flip over as  I did she lifted the towel professionally blocking any potential view of my dick.

She began massaging my chest and slowly worked down to my abdomen.  She had positioned her body over my head so as she leaned forward her breasts were right in front of my face.

I let myself become hard and formed a small tent under the towel.  She moved to the side and massaged my legs and abdomen near my package all but coming into contact with my cock.  Obviously this had the desired effect and I became fully erect.  She stopped and as she knew it was my first time she explained to me what the options were.  Hand job, topless hand job, or fully nude hand job and she told me what the generally accepted tips were for each.

Being my first time and at such a young age, I was lucky to have any money left over for extras but I had just enough to request a hand job.  This masseuse must have been feeling generous, on the other hand I think she enjoyed the fact that I was quite a bit younger but she offered a free upgrade to a topless massage which I gladly accepted.  She disrobed and continued to massage my chest and came around and kissed my lips before removing my towel and teasing my cock with her hands.

She told me that I was allowed to touch her tits and she placed my hand on her.  As I squeezed her tit she came back and kissed me again.

She loaded up with baby oil and started stroking my cock while I continued to feel her tits.  She seemed to be enjoying herself and returned to kiss me some more as she stroked my cock.  I was enjoying myself immensely when I thought it can not hurt to ask for a blowjob, and at first she declined.  However, I persisted and said it sure would be nice to finish with BJ, she finally agreed but pleading with me not to tell anyone since she would lose her job and she would not want other customers asking for the same.  I agreed and she moved her lips to my cock, wrapping her lips around the head of my dick and moving her tongue around its girth before bobbing on my cock.

It was not long before I filled her mouth with cum and watched her swallow.  She took her time coming off my cock and gave a few extra strokes before wrapping her mouth around my head again to capture every last bit of my cum.

She robed and left the room to redress.  I put my clothes back on as well and she returned so that we could finish up our business.  A great first experience I must say, and not one that I think I could reproduce.

I have since visited many massage parlors in Ottawa and this has been the one and only blowjob that I have received.  I have had a few girls give my dick a kiss or two but never another full BJ. I do not recall any other masseuse who would kiss on the lips either.  I continue to visit massage parlors when the opportunity is there and almost always have a positive experience.  In general, the women are younger than my first masseuse and nearly always even hotter.  I would encourage any man or even women who may be bi-curious or bisexual to treat yourself to this once in a while.

My only other comment is that the Ottawa parlors are nice and pleasant experiences.  However, I once visited a parlor in the Toronto area (GTA MothaFucka!) and was happily surprised that the experience was even much more positive.  They start you off with a photo album of all the girls working that day and you choose the one you want.  Even more services and perks such as hot tubs etc... that are generally available in Ottawa.  I had an enchanting evening there with a lovely black women with very large yet perky and natural breasts.

For those of you that may have thought I have a thing for girls in their teens, this is not true, only I have several experiences in that area.  However, I also have many many more experiences that do not include teens.  Stay tuned... more to come...

Leave me your feedback and comments.  I would love to know what you are thinking about my blog and where you would like to see it go next.