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Archive for July, 2008

Dear Tryst – Naughty Nurse

Thursday
Jul 31,2008

Dear Tryst:

I had been trysting with my secretary for about six months when I really put my foot in it.

The affair I’d been having with my secretary (let’s just call her Jane) was far more sexually adventurous then the relations (or lack thereof) I was having with my wife. Wanting to take it up a notch, I visited a local sex shop, intent on buying Jane some role-playing gear. I had always liked the idea of seducing a naughty nurse, so I purchased a barely there vinyl nurse uniform for her. I took my purchase up to the cash register, and was asked if this was for a special occasion. “We can gift wrap and deliver the package for you,” she said. What a great idea, I thought. I’d have it sent to her Saturday afternoon, with instructions for her to wear it when I came to her house that evening. So, with visions of sponge baths and complete physicals running rampant in my head, I jotted down the address for the cashier and left, congratulating myself on such a masterful surprise.

The appointed Saturday finally arrived, and I spent the morning running around, getting the necessary supplies our evening required. When I finally came home, my wife was waiting for me in the living room, an enraged look painted on her face and a familiar-looking parcel unwrapped on the floor.

“What the hell is this?” she exploded, throwing the contents of the package in my face. I guess I was so wrapped up in my fantasy, I had given the cashier my home address instead of Jane’s. Panicked, I started thinking of excuses, trying to come up with reasons why I was having the affair. Before I could stammer any of them out, she screamed, “Do you think I would actually wear this?” After calming her down with hurried apologies, she suggested that I needed to think about the consequences of my actions by spending a few days at a motel. Without seeming to be too eager, a packed a few essentials – including the nurse uniform – and hastily beat a retreat to Jane’s house. Not only did I escape a costly divorce, I also had the most incredible four days of non-stop sex with an extremely naughty nurse.

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  • Dear Tryst – Max

    Thursday
    Jul 31,2008

    Dear Tryst:

    Awkward doesn’t even begin to describe the day I found out that Max, my paper boy, had a second delivery job. Let me start at the beginning:

    I live in the most perfect little neighborhood, in the most perfect little home, surrounded by a perfect white picket fence. I married my college boyfriend as soon as we graduated, and he makes enough money for me to stay home and actively pursue my interests, which includes lunching at the club with the other girls in the neighborhood and spending my husband’s money engaged in some retail therapy. Oh, and then there’s Pete – he takes up some of my free time too. Let me explain – living an idyllic life isn’t as grand as it seems. It can be mind-crushingly boring. That’s where Pete comes in. We like to get together once a week (sometimes more if the hubby’s away on business) to partake in mutually enjoyed pursuits – and earth shattering ones at that!

    I needed a little vacation, so I told my husband I was going away on a girl’s weekend for some shopping, gossiping and harmless fun. What that really meant was shacking up with Pete at the Hilton on the edge of town for some bedroom gymnastics. It started out swimmingly. Hours upon hours of good ole fashioned trysting works up a mighty appetite, so we decided to order a pizza, and since we didn’t feel like dressing, delivery was the most reasonable course of action. Thirty minutes later, and I answered the door wearing nothing but a big smile and Pete’s button down shirt. You can imagine my surprise when I was greeted by a familiar face – Max.

    He recognized me as soon as I opened the door, and I could tell that he was a bit confused to find me there. That look changed to pure amazement when Pete came up from behind, took the food from startled Max, then smacked my ass and told me he was hungry for more then just pizza. I think Max finally realized what was really going on when I tipped him a $50 – he gave me a knowing smile and wished me a pleasant evening. Thanks to that tip, my tryst didn’t make news headlines the next day!

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  • Dear Tryst – Cutiepie30

    Thursday
    Jul 31,2008

    Dear Tryst:

    I’ve always wondered what it would be like to be with another woman.  These thoughts have gotten stronger over time, especially over my decade long marriage.  Hoping to satisfy my hunger, I’d just watch some porn with the hubby only to realize I was fueling the fire.  I even broached the topic of inviting another girl into our bedroom, but he wasn’t interested – his reasoning is that if you’re having sex with someone other than your spouse (even if they are participating), it qualifies as an affair.

    My husband was out playing golf, so I had a few hours of uninterrupted time to myself. As I was checking my e-mail, a link to an X-rated dating website came up.  Intrigued, I clicked on it and browsed the site.  In no time at all I had created a profile, indicating I was interested in exploring a little girl-on-girl action.

    After a few days I received some responses from women, many in similar situations.  One profile in particular stood out for me – “cutiepie30” – a hottie who gained my attention thanks to a profile picture of her perfect breasts.  We e-mailed back and forth for a couple of weeks, really hitting it off.  We had the same fetishes, likes and dislikes, lived in the same city and we both had never experienced another woman before.  She was married as well which eased my concerns of discretion – we hadn’t posted any facial pictures on the site for this very reason, it was just too risky.

    After working ourselves up to a fever pitch, we decided it was time to act on our urges.  A date, time and place were worked out.  We would meet at her friend’s condo (she was out of town at the time, and cuteipie30 was checking in on her cats). After grooming myself meticulously and providing an appropriate alibi, I went to meet my mystery woman.

    When I arrived I was so nervous and turned on, I could hardly stand it.  A husky voice over the intercom invited me in, and I tried to calm myself as I rode the elevator to her floor.  I gathered my courage and knocked on her door.  My jaw almost hit the floor when the door opened and there stood my sister-in-law!  We were both speechless, and not knowing what else to do, I invited myself in.  It was a little awkward talking at first, but I reminded myself that I had always thought she was very attractive.  She admitted she had the same thoughts about me, and before long, we acted out our sapphic fantasies.

    We met up a few times since then – it’s the perfect hookup.  I’d just tell my husband I’m hanging out with his sister, which was true!  I wonder what Thanksgiving will be like this year?!

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