Sissy Gurlfriend Part 5
Sissy Gurlfriend Part 5
by Bill Beaumonte (oral_guy_2000@yahoo.com)
This work contains explicit material intended for adults over 18. If you are under 18 or are offended by non-traditional sex, do not continue.
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Author’s note:
_A high school guy finally finds dating success with an unexpectedly different girlfriend. I hope you enjoy this work of fiction.
_
F riday finally arrived, and I told my mom and dad that I would be staying at Jason's (a friend), as a cover for my overnight with Kerry. I let Jason know just in case my parents tried to contact me there, though it was unlikely.
I changed my clothes after school, packed a change of clothes and grooming items and went to Kerry's before my parents were home. Since it was next door, I'd have to be careful not to be seen by them when we went out.
Kerry greeted me at the door and we immediately kissed. "I thought maybe you could begin prepping me," she said, "And you can do more later."
That sounded great to me, so I followed Kerry to her room and helped her undress. She stood before me naked and was just so beautiful I had to take her into my arms and kiss her again, gently squeezing her buns as I did.
"I really like the attention you give me there," she said, which of course urged me on further. With my finger I traced along her crack a couple times, and then slipped between her cheeks and touched her tender pucker. Kerry kissed me even more passionately, so I knew it was time to go further.
I led her to the bed and had her on all fours with her feet over the edge of the bed. I got a tube of lube and set it next to her as I knelt on the floor next to the bed. I spread her cheeks and kissed her deeply, wishing I had a really long tongue like Gene Simmons, of the musical group Kiss. I realized that sticking my tongue into an anus was pretty kinky – I went in as far as I could and Kerry loved it. I loved Kerry, so I would do it as often as I could. I was truly blessed that she was always what I called "kissing clean", so it was as delightful for me as it was for her.
Kerry moaned with delight and pushed back against my face, as if trying to get more of my tongue into her. I eagerly gave her all I had, wishing I could do better. I rimmed her for a few minutes before my tongue got tired. I hoped that with practice I could do it for longer. I backed away and squirted some lube on a finger and pressed it into her to my first knuckle.
"Oooh that's nice too – keep going," she said. I pressed my finger in all the way, feeling her soft wetness with my fingertip as I moved it around in her.
As I stroked my finger in and out, Kerry said, "That's gonna be even better when you take me later."
"I want that as much as you do," I assured her. I withdrew the finger and added lube to a second finger. I pushed one in and then gently pushed in the other, taking care to go slowly.
Once both fingers were in I said, "Now I'm going to spread my fingers – you tell me if you feel even a little pain and I'll stop."
I spread my fingers while rotating my wrist, so the various parts of her anus got gently stretched. I was worried I might hurt her, but she seemed to handle it well. I withdrew and lubed another finger, and then inserted three fingers. As I spread all three fingers Kerry said it began to hurt, so I stopped. She was definitely ready, and I could see that her clitty was fully aroused.
I pulled out my fingers and decided to try something else. I had Kerry roll over on her side, exposing both front and back to me. I slipped two fingers into her all the way, and then took her clitty into my mouth. Then I began to wiggle my two fingers back and forth inside her and it drove her absolutely wild!
She began to buck and soon filled my mouth with her gurl juice. As she pumped into my mouth I could feel her anus tighten around my fingers.
"Where ever did you learn to do THAT?!" she asked.
"I just thought it up myself and decided to try it," I said, "Does that make me an inventor?"
"That works for me," Kerry said, "Though I don't think you could ever get a patent for it."
I went into the bathroom, washed my hands and brought back a wet soapy washcloth to clean Kerry. It was only lube, but I thought it might be a little gross to lick it of, so I wiped her clean instead.
"That part was wonderful," Kerry said, "Am I fully prepped now?"
"I think you'll be ready," I said, "But I still want to take it slowly, just to be sure."
"You're such a great guy, Bill," Kerry said, kissing me once more.
I helped her get dressed, including hooking up a pendant and bracelet, since we were going out for a movie after dinner. Kerry touched up her makeup – always the perfectionist, and warned me about not smearing her lipstick when we kissed.
I thought that was unavoidable – more often than not I kissed the lipstick right off her!
We went to the living room and watched TV, holding hands and stealing a kiss now and then, until Kerry's parents arrived home.
Kerry went with her mom to prepare dinner while her dad and I talked in the living room. It was a much easier conversation now that I wasn't being grilled. It did seem kind of strange with him knowing I'd be fucking his daughter later that night, and him helping me celebrate it.
We were called to dinner and took our seats. In honor of the occasion Kerry was asked to choose the meal and she chose beef stroganoff, which was one of my favorites as well. Kerry's mother told me about some of the family traditions – I suppose that was her way of welcoming me in.
Later her dad said, "It's kind of tradition for a girl to save herself for marriage, but that's kind of outdated. Most important is for a girl to offer herself only to the man she truly loves – who truly loves her."
"I think that describes us perfectly," I said, and Kerry agreed fully.
"There is some wisdom in that beyond avoiding unwanted pregnancy," he said, "Sex and love don't always happen at the same time."
"You can have love without sex and sex without love," he continued, "But when you put them together, it's like being supercharged!"
"I think that's true," I agreed, "Even just kissing, it's so much better with Kerry than with anybody else!"
Kerry's mom poured glasses of wine for all of us and her dad offered a toast, "Here's to the union of Kerry and Bill – may it always be filled with joy!"
I couldn't have agreed more and was glad Kerry's dad wasn't prudish about sharing alcohol with me.
After dinner Ken drove us to the Symphony Hall, where her mom had bought us tickets. They must have been expensive because they were good seats, and tickets to live performances weren't cheap.
It was a great performance of Vivaldi's Four Seasons. We didn't have the opportunity to make out, but did hold hands most of the time. At intermission I took pictures of Kerry with various backdrops, though she was always far more lovely than the backdrop.
After the performance Ken was waiting for us and took us home. We thanked Kerry's mother for treating us to such a wonderful performance. She reminded us that we had some things to do upstairs, and that we should get to it. We needed no further encouragement and promptly adjourned to Kerry's bedroom.
We undressed each other and caressed. "I'm kind of nervous about this," confessed Kerry, "I want it badly, but am a little afraid."
"Let me prep you some more," I said, "And then I'm going to ask you to do a particular position that will make it easier."
"I trust you completely, Bill," she replied, "And will do whatever you say."
I positioned Kerry on the bed and rimmed her for as long as I could. I planned to do this often and build up my stamina. I worked lubed fingers into her, opening her, and then I felt she was ready.
"I'm going to lay on the bed, and want you to lower yourself onto me," I explained, "It's called the cowgirl position, and will let you control the rate of entry and how deep – just take it slowly."
I got in position and watched as Kerry straddled me and began to lower herself. She paused to position herself as my cock head touched her, then her warm wetness felt so incredible!
The look on Kerry's face was amazing as well, with her eyes open wide as she took me in all the way. "It's so wonderful to feel you inside me," she said, beginning to bounce up and down, "But I'll bet it would be better if you were on top – could we try that?"
Now that we knew entry wasn't a problem, I told Kerry we could trade places. She got off and lay on the bed as I positioned myself with her legs up my chest and over my shoulders. I easily slipped into her, since she was quite ready. I held her legs to me as I thrust in and out, gently squeezing her nipples along the way. Kerry's clitty was hard, and bouncing up and down. I put a little lube on my hand and fondled her clitty, paying particular attention to the head, which really made her moan!
After a few minutes Kerry climaxed, and I experienced the wonderful feeling of her tightening around me with every squirt from her clitty. That was enough to send me over the edge, and I climaxed, merging my seed with Kerry. It took a few minutes for us to recover, but then I withdrew and went to the bathroom to clean up, returning with a wet washcloth, cleaning Kerry.
"Always such a gentleman," she said. I returned the washcloth to the bathroom and we both got ready for bed. We got into the bed and lay there spooning, with my arm around Kerry, hand on one of her breasts. It was a wonderful feeling after our joyful lovemaking, and we drifted off to sleep.
To be continued . . .
Feel free to contact me with your comments or requests.
–Bill Beaumonte (oral_guy_2000@yahoo.com)