My Old Friend Jill
Tem 14, 2022 // By:analsex // No Comment
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My name is Steve and this is a somewhat true story that occurred a few years ago when my best friend from high school, Art, was about to marry Jill, who was also an old high school classmate. By this time we were all in our late 20s, but Jill was one of those women who had everything going for her. She was not only a very good looking lady with a terrific body and a to-die-for smile, but was also brainy having gotten a full scholarship to Cornell where she studied biochemistry before getting a Ph.D. in pharmacology from Johns Hopkins. What wasn’t there to like?
To give some history I had dated Jill a couple of times in high school and she was even my date to the senior prom. We really liked one another, but that is pretty much where things ended as we never had sex and for that matter never did much of anything else than some mild necking. I was still single and have to admit that I was very envious of Art, but he had been a nearly lifelong friend. His older brother was going to be his best man but he wanted me to be one of his groomsmen. I readily agreed.
It was to be a mid-September wedding on Maryland’s eastern shore with a reception at the Inn at Perry Cabin, a very posh location on gorgeous Chesapeake Bay. It was a convenient enough location being only a couple of hours from where I was living at the time in Philadelphia. I like being on the water and love sailing so I took a couple of extra days and on Thursday went out on the bay with some old fraternity brothers. Despite the light rain that lasted all day, but as sailors with appropriate foul weather gear, we still spent hours cruising the bay. Afterward we found a great seafood restaurant where we relived many of our college experiences. Afterward I wound up at the Inn, registered and got to my room, well not so much a room as a suite–it was awesome.
After I opened my luggage and checked out the bathroom, I found a bottle of Yuengling in the mini-bar and settled in to watch TV. The beer tasted good despite being my fourth of the evening. I tuned into the baseball game and fortunately it was the Phillies playing a doubleheader. Just as I was getting interested there came a knock at the door. I sort of cursed the interruption because the game had just gotten good as the Phillies had bases loaded. Nevertheless, I answered the door.
There stood a tall brunette woman wearing cargo shorts, tee shirt, boat shoes and a yellow foul weather jacket that glistened from the rain. It was Jill.
“Hi,” she said. “I heard that you got in a day early so I thought I’d come around and say ‘hi’ and maybe we could have a drink together. You know, for old time sake.”
“I’m glad you did, but let’s get you out of that wet jacket,” I offered.
“Oh, thanks. Yeah, it’s pouring out and I got drenched just coming from the car to the lobby,” Jill said taking off the dripping rain jacket revealing that she hadn’t had it zipped up and her tee shirt was wet enough to cling to her body revealing the wonderful set of boobs being held by a sexy lace brassiere. Clearly, she had grown one impressive rack since high school.
“You’re looking great,” I began but not bahis şirketleri being able to take my eyes off her chest. “So, are you looking forward to getting married on Saturday?”
“I am plus I think I’m ready. I’ve worked plenty hard to get where I am and am fortunate enough to have landed a great job with a leading pharma company. Besides you’ve known Art for as long as you’ve known me. We’re perfect together and I’m looking forward to bearing his children.”
“You and I did have a fun time during high school. I’m just sorry that we lost track of one another.”
“We did even if we didn’t date that long. It kind of ended when you took me to the senior prom. You were so handsome in your tuxedo. Seeing you wearing one this Saturday will give me some flashbacks, I’m sure.”
“Can I get you a drink?”
“Sure, A beer? Some wine? What would you like?”
“A beer would be fine, thanks. I had no idea that I would get so wet coming in from the car. Can I use your hairdryer to dry out my tee shirt? It’s wet and I’m getting cold.”
“Sure. Come on,” I said leading Jill to the bathroom and getting the hairdryer for her.
“It might work better if I took the shirt off,” she said slipping the wet shirt off and further revealing her great body. Jill could not have found a better brassiere to wear save going braless. Its demi-cups barely covered her nipples plus it revealed an ample amount of her cleavage. Taking in the view I was already feeling my manhood coming to life.
I held the shirt up as she worked the dryer, but it was apparent that this would take a lot of time. “How about we put the shirt on a hanger, aim the dryer at it, and go back and finish our drinks?
We returned to the sitting area where the conversation returned once more to our high school years. “That prom was a lovely event,” I said. “And you looked unbelievably sexy in that long turquoise gown.”
“Yes, I even remember going shopping for that dress. My mom thought it was too sexy because I didn’t have to wear a separate bra with it.”
“Now that’s a piece of information that I was not aware of.”
“She was afraid that the prom would live up to its reputation and that we would have had sex that night.”
“Well that didn’t happen. And certainly if it had happened, it would have been memorable.” I quipped perhaps without thinking.
“Yes, it would have been, but I guess things always work out for the best. We weren’t ready for that.”
“No, I suppose you’re right. Not like now. Are you ready to get married?”
“I am, but there is just one more thing that I feel I need to do before that happens and Saturday will be here before I know it,” she said getting up, coming over to me and sitting on my lap.
To say that I was caught off guard would be a huge understatement. The last thing in the world that I would have thought that I’d be doing this evening is having a romantic encounter with the bride-to-be. Jill sat there wrapped her right arm around me and then with her left proceeded to twirl the hair on my chest before moving to my nipple. While she had found its profile showing through my golf shirt, bahis firmaları moments later she had reached inside. The sensation was electric and I could feel my manhood immediately go from just twitching to fully erect.
Sitting on my lap also put her cleavage at exactly eye level. How tempting and it should come as no surprise that I gave into temptation and planted a kiss on her right boob., its perfect flesh feeling soft and sensuous to my lips.
“I could make that a little easier for you,” Jill said with an innocent giggle as she reached around her back and unfastened the hooks. The bra immediately surrendered its contents allowing me free access to touch, gently squeeze, and otherwise sensuously fondle the treasure that they were.
“Oh, don’t stop doing that!” she exclaimed. “We might not have dated long enough back in high school, but that doesn’t mean that we can’t make up for some lost time.”
The prospects of bedding this very attractive woman was enticing. Plus, she was right, back in high school we hadn’t been together long enough to get to first base. Tonight, however, I was already thinking that there would be a home run. Maybe even two if things go right.
Just as those thoughts were crossing my mind, Jill got off my lap. I was worried that things were ending before they ever got started, but I was wrong. “These shorts are just going to be in the way,” she explained as she unbuttoned and then unzipped the cargo shorts. In one single motion she peeled them off her hips, let them fall to the floor and stepped out of them. “There, that’s better,” she offered as she slipped the brassiere off her shoulders. “Now it’s your turn!”
I learned years ago that weddings are the perfect occasions for getting laid. For one, the attendants are usually young and nubile; second, there always seems to be a lot of estrogen about; and third, everyone knows that a wedding is a ceremony where a woman is officially giving a guy her vagina. Now there is nothing better than being in the wedding party and paired up with one of the attendants. This was speaking from experience because there has been more than one bridesmaid that I have brought back to my room. Never, however, have I ever gotten to bed the bride-to-be, but that was about to change as I peeled off my golf shirt and took down my sailing shorts.
“Now that we’re both standing here in our undies, what do you think we should do next?” asked Jill.
“I don’t know. Maybe watching the rest of the ball game?” I teased.
“Oh, there will be a ball game alright, but it isn’t going to be on TV either,” quipped Jill now putting her thumbs inside the waistband of her bikinis and slipping them off. “You’re next!” she exclaimed.
I was no sooner standing there in my altogether when Jill dropped to her knees and took my manhood in her mouth letting her tongue tease its very tip. It had been some time since a woman had performed fellatio on me and all I can say is that Jill was really good.
‘Don’t you dare cum in my mouth,” she cautioned. “There is only one place that I’m going to allow you to finish and that place is my cunt.”
I wasn’t kaçak bahis siteleri going to be able to restrain myself for too long and told Jill as much. Knowing that time was of the essence, she stood up, turned towards the back of the sofa, and bent over. I entered her from behind allowing myself to penetrate her the full length of my organ. Jill purred with satisfaction, but after a couple of in and out moves I deposited my load deep inside of her.
“Oh, but do I ever love cum!” she exclaimed, “but there has to be more where that came from. At least I hope so.”
“There is,” I assured her.
“That’s good but before we get to that, you have to eat me. I’m thinking that I’ll be tasty enough with my pussy juice blending with your cum.”
Having never tasted my own cum under such circumstance I only had to think about it for a mere instant as the thought of tasting Jill was more than enough to offset any reticence that I might have had. We made our way to the bedroom where she laid down on the bed with her butt just short of hanging off the bed and then I knelt on the floor and buried my face in her dripping wet muff. I licked her shaved smooth pubis and let my tongue explore her in search of her clit. It didn’t take long before I was sucking on it, an action that caused her body to exude even more pussy juice. I licked more of it up, but her body continued to produce an even greater amount.
Finally, I felt that it was time to fuck her once again and I stood up, took one of her legs in each hand, spread her and allowed by manhood to enter her now very wet and slippery vagina unaided. As I moved in and out she moaned with delight. I lost count but think that she had cummed three different times before I shot another full load into her. Each of us breathless we collapsed into one another’s arms and fell asleep for several minutes.
When we awoke, Jill looked at the clock. “Oh, my gosh, but I had no idea that it was so late. I’d love to spend the night, but that would be hard to explain in the morning. Instead, why don’t we do it just one more time for old time sake?”
One more time? This woman is insatiable, but I replied, “Sure, why not. What position do you want to use?”
“I want to feel you. I mean really feel you so let’s do the cowgirl,” Jill said as I got on the bed and laid on my back. Soon Jill had positioned herself on top of me and lowered her incredibly wet pussy onto my phallus. Once again, I was inside of her and really deep at that. She had to ride me for some time before I came, that being the third time that evening. As with the other times Jill could not ever get enough cum, but soon all three loads were draining out of her and onto my loins. It was messy, but it was a night that I’ll remember forever.
Two days later I was at the church. The organist started to play the processional and Jill’s dad walked her down the aisle. Standing with the other groomsmen at the front of the church I couldn’t help but admire what a fine-looking woman Jill was. Moreover, she looked so virginal in her white gown, but then I flashed back to barely two days prior and a smile came over me. “Hmmm, yes, virginal!” I thought to myself. As Jill and her dad arrived at the front of the church she looked in my direction, a faintest of smiles came to her lips, and then gave me a naughty wink.
What a wedding week that was.
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