Jennifer's Birthday Paddling - Sex Stories

Jennifer's Birthday Paddling

Synopsis: Very Long story. Jennifer and her friend Linda get a paddling, and Jennifer gets her rectum pleasured by her friend. ---------------------Jennifer's Birthday Paddling Jennifer was really a sweet catch, and an older woman to boot. I had been working a Real Estate office for 2 years in sales, and she joined the company in May of 89'. I immediately liked Jennifer a lot, not only because she was older but had a very sweet and kind air about her. I was 27 at the time, and Jennifer was a bit older than me (closer to 40 I guessed). I have always enjoyed the company of older women since my mid twenties. The have their acts together, know what they want, and are at their sexual peak. The other thing I liked about her was that she was rather plain looking, but had a big heart. Most of the other sales guys I worked with were too busy screwing 20 year old coeds from the surrounding colleges, or swilling beer and generally lying about their conquests. They wouldn't have touched Jennifer with a ten foot pole, and that was fine by me. Personally, I thought Jennifer was great. She was about 5'4 - slim figure, and beautiful wavy hair cascading over her shoulders. She never liked to wear makeup, and I think that's why she looked rather plain. However, looking plain myself - I figured we might get along famously, and we did! She also had the most smoldering green eyes I have ever seen, and they sometimes glinted with mischief when you would talk to her. She also likes to touch you ...

... when she spoke. Sometimes softly on the arm, or the hand. Our courtship was a wonderful experience - intimate, romantic, and filled with expectation. She was absolutely a great lover, and could get me up and running sometimes four or five times in one night. During that summer, we had gotten into some light spanking during our lovemaking sessions. Nothing too serious, 20 or 30 light swats to warm her bottom and then a long night of lovemaking. She was always alluding to getting spanked, and would find all sorts of ways to work it into the conversation. After a while, we tried to get the spanking routine into almost every Saturday's lovemaking. Jennifer has a strong will (stubborn), so even then I found that the spankings were more her idea than mine, with her asking for it, and me responding... This was soon to change.... We'd been together for about nine months, and I realized Jennifer's Birthday was less than a week away. One night on the phone, I started asking her what she'd like. It was to be her fortieth birthday (a biggie as they say), and I really wanted to treat her to something special. A nice dinner, some presents, a hug and a kiss, whatever she wanted... "So Jen, what would you like for your B-day?"... This was after ten minutes of prying and prodding. "Well, what can you get for the woman who has everything?" I joking said (knowing she'd like this), "How about a Birthday spanking you'll never forget?” She paused for a moment...there was silence on the line. "That ...