A Year Ago Ch. 15

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Sara Dates George.
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4.66
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Part 15 of the 19 part series

Updated 06/07/2023
Created 12/10/2014
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MadQuill
MadQuill
358 Followers

This is an evolving story of Sara's sensual investigations. Please review the first phases of the story . . . Sara's life change has entered the fourth month and her world feels very new, very much hers.

*****

On the drive to the office Friday morning I thought back to George and my second date almost a month ago. I had been a little drunk but knew what I was doing when I unzipped his pants and slipped his hard cock out.

As I licked about the length of his generous phallus I consider how moist my thong was. During the dinner I was relaxed but also quite excited. Now with his stiffness in my hand I needed to go slow. I had no intention of losing my cherry tonight. He had resisted my forwardness as we reached the passenger door. I was kissing him deeply as my hand rubbed him softly through the pants. I was responsible for his erection and wanted to have him in my mouth.

With my toy Sam it was easier for my teeth weren't an issue. My study of cocksucking was clear; take the cock slowly into the mouth and prevent your teeth from scratching the sensitive skin of your partner.

I started by licking along the side and then used my lips wrapped about the girth to move back to the helmet. I looked to George and he smiled as I engulf his big cock. He could only last for about a minute and his juice hit the back of my mouth. I was surprised how similar his tasted to my own. He pulled me off of my knees and kissed me a moment later. His tongue found some of the seed.

"That was great Sara. I've had many blowjobs but none as special as your mouth." His hand was on my upper thigh but it had been there a great deal that night. He had enjoyed my silky stocking and the bare skin above the hose' welt but had resisted moving his hand to my panty until now.

I reached to stop him, "I'd rather wait George. I'll be more prepared after the appointment. Please just hold me. Did I really do okay?"

"You did very well for a beginner," I'd shared that I was practicing at dinner. He was curious if I'd ever been with a male. "So this, I mean I'm your first boyfriend?"

"Yes George and you're a great reason to be a woman. I enjoy spending time together with you. The gentleman approach is working. This girl likes you." I blushed and he reached to hug me. We were in a booth and the restaurant wasn't crowded.

His cock was a bigger than I thought but the larger new toy I'd received earlier that week was helpful. I hadn't name the eight-inch long thicker toy. It was an uncut version for I wanted to understand if there was a difference. George was circumcised so I wouldn't name that fat phallus quite yet.

- - - - -

Once at the office I wasn't able to focus and besides there wasn't a lot to do, as it was Friday. I'd had lunch with Avery and we spoke mostly about the recovery and my chest.

"Madison was certain that you'd select a fuller size. Since I'm pretty small I think a large bosom might be nice but yours are just right Sara. I've been watching Madison deal with bras that aren't comfortable for years. After five-thirty many days she removes it. I've never had that issue. Are they sensitive?"

I smiled slightly and bent to get a little closer, "Actually I had excitable nipples before the surgery. Now I'm no expert, but on my own I've found that the stimulation can be distracting. Just moving too quickly can cause me to, well not cum but I definitively get excited. The Doctor has told me that I can run in another two weeks. The team was quite happy with the results and to me, well, having them makes me feel a bit more womanly."

She snickered slightly, "I'm sorry but you sound crazy Sara. You couldn't be more of a woman. Your face and butt lead this lesbian to distraction!"

I was happy for her offhanded praise but I still didn't feel completely female either. The hormones had slightly affected my testes, and tucking was easier since my penis was a bit smaller.

She knew I had a date, "Tonight with George I hope to find a new sense of enjoyment. Playing alone just isn't as fun."

Again she snickered, "I'll come play with you Sara, can I please?" We both laughed at her come on.

"But seriously, your nails need attention. What will you wear?"

I told Avery of my planned outfit. How I decided on the new black dress.

"Sexy yet not over the top or slutty. Maybe not the hose' though. Have you tried a pair of suspender hose?"

I said, "That may be better. I've got a pair in light charcoal with a lace top."

She continued, "And are you truly prepared for having a, I mean, I like it when a girl fucks my butt but I've been taught over several years and been with many lovers. Actually it was Madison, when we were lovers, who took my bottom first."

I liked that Avery could discuss anything with me. She hadn't been shy about any of the details of my transition. "Well I'll of course clean my bottom and the toys have allowed me to become accustom to,"

She giggled, "Who is this mystery lover?"

"Yeah Avery, I've been fucked by one named 'Sam' many times now. My newer toy is closer to George in size and though not warm it seemed pretty nice inside my bottom."

I had shared the fellatio episode.

She smiled and said, "I actually love the ritual in cleansing. Getting clean for my lover."

I smirked, "I'm surprised how many girls, I mean to say lesbians, love to play with their bums."

Now she smirked, "After practicing to get accustom to the penetration I find the orgasm can be more intense Sara. Not always but something in my backdoor can be exciting with the right girl."

Hearing her I wondered how I'd missed this sexual activity prior to twelve weeks ago. She was right and yet I had been resistant to anal.

"I think George has been, he's had a male lover. I hope he can lead. I seemed to want to be at least somewhat submissive."

Avery smiled, "Yes Sara, and Angelica will be waiting for you too."

"Why can't we be both, I mean, being submissive, dominant or whatever? Is it that obvious? How can you tell? How could you and Madison sense she wants me?"

Now she laughed, "That first sight of you weeks ago, I have to say you looked so much in need of care. Yes we can. It does depend on whom you're having sex with Sara. To your last question, I of course didn't recognize you as Michael at that moment. You may not believe me but I was attracted to you in that blink moment."

I reached across the table, "I needed you as a friend, and I still do Avery. Thanks for your support."

"But that cougar wants you. Angelica seems to prefer female lovers, though she isn't a typical lesbian. She is a bit too glamorous for most femmes or lipstick babes. Be careful playing with her. She knows everything about you correct?"

She understood as I spoke, "The tenant agreement was the tell though."

"Ahh, yeah that makes sense Sara. Michael's name had to have been in the files."

She paused, "But we need to get you focused on the other sex. Your date tonight could change your sexual perception Sara. I mean, I haven't met this guy but if my experience shows anything, you're either into girls or guys. There are some women who are true bisexuals but they're few and far between. That doesn't mean the best femme dykes don't love to be penetrated. That's why we have all of the toys for god sakes. I don't think that most straights can separate the act of penetration from gender selection. Females get to be more fluid in our selection of mates. Now you can as well Sara."

On the drive home I recalled the last meeting with Angelica. I was entranced by her powerful and sensual personality. She held my attention but I had to showered and prepare for the date with George. Tonight I hoped would change something about me. Just the experience of having another in bed after weeks by myself would be good. That George was a man who treats me as a female may be a risk. Avery had mentioned that as well. 'Be prepared for anything. He may be aggressive even if his behavior hasn't been'.

Her final words caused me to think, "Remember that whether or not you asked for him to go to bed with you, you can always change your mind. Saying no is a woman's option at all times Sara." We agreed to meet at the Park for a walk Sunday morning.

I found the package of suspender hose' and spent thirty minutes attending to my nails. I had a DVD running that showed Claire with various men, only men. I had watched the movie earlier in the week to understand how her acting changed when she was with men and I noted the subtle details of her submissive role. Claire could handle the role and yet could be the top with other women. Watching a big penis pushed inside her tight body had helped me during my initial attempts. Now I wanted George inside me.

I wanted to be fucked, on my back, standing against a wall, from behind and even reverse cowgirl. Maybe we wouldn't get to all of these positions but I wanted George to thoroughly settle my bottom on his cock.

Now dressed in the hose', just a black thong and my black four-inch slingbacks I wandered to the Hall mirror. On our previous dates I hadn't worn a wig but tonight was special and besides, I needed a trim. So with the honey blonde hair falling to the middle of my back I studied my body. My breasts were nicely shaped and the areolas and nipples had increased beautifully. The small scars at my armpits were barely noticeable after four weeks.

Touching my new breasts lightly was enough to get me excited, actually more exciting then the nipples. The lower skin was very sensitive to my touch. I hoped having George's tongue on them would be equally exciting.

I would wear a support bra but I wanted to review my face and hair before completing the outfit. I wondered why black lingerie seemed correct. I was of course about to give away the only opening I had to a penis. Was this event sort of like a wedding? Should I re-consider the ivory outfit?

I stepped back to the bath to adjust my eyeshadow and apply the lipstain. My toy play had shown me how lipstick just wasn't feasible. It rubbed off within seconds and smeared the toy skin. With my dark charcoal chemise on I lightly applied the Chanel perfume. I stepped into my body-con dress and pulled it up and over my new breasts, and zipped it into place. I wondered at how the fabric with just a bit of spandex hugged my now narrow waist and clung to my hips. The hem fell past mid-thigh but still seemed short to me. The neckline wasn't too deep and it felt good moving about completing the last of the outfit. I only needed to set the hoops in my ears and slip on my bangles. I heard the car outside but paused. George must come to the door and ask me to join him.

I was pretty certain he knew that we would be in bed later. I'd hinted that the restaurant I wanted to go to had a nice Hotel. I would insist that we get a room to avoid Susan seeing his car tomorrow morning. Sneaking about felt a little silly.

The bell sounded and I gather my purse and small bag. The five-pack of condoms I hoped would be sufficient. In the other bag was an outfit for the morning and an extra thong panty. The last date I had soaked my panty early and it was less than comfortable, as I had sucked him off.

The Date went well but I was distracted. All during dinner I kept seeing this man as so near to being with me.

"I can't eat George. Take me upstairs please?" He had already checked in.

"Sara relax, we've got all night". He had a steak and I ate a few scallops and resisted drinking the third glass of wine. Two hours later he asked for the check.

His cock was stiff as we rode the elevator to the fifth floor. Maybe it was hands rubbing his back as we rose in the elevator. His hands found my breasts secured by the sexy black lacy bra.

"The doctor recommends that I wear the bra during sex for at least another week George, okay?"

At the door I pushed it closed and kissed him, "I want your cock inside me George. Fuck me please," but he said, "Let me look at your breasts Sara," as he stepped back.

I slowly removed the tight dress and the chemise fell to the carpet. I left the thong on.

"I want to keep this on please. I feel feminine when my clit is restrained please.

He came and hugged me, "Then at least remove the bra to let my eyes enjoy your body Sara."

I released the bra and he came and kissed my mouth then slipped down to the right breast licking along the underside just below the areole, then he moved the left.

"I love your breasts Sara," he continued to lick and tease the erect nipple of my left breast.

He stood to kiss me as my hand found his belt and released the clasp.

I reached for his smooth cock after pushing the pant down, "This is my joy tonight. Are you ready to fuck your new woman George?"

After he first licked my opening he stood near with me on my back on the edge of the bed with my heels on the floor. He ran the very hard and big cock along my thong. I thought only of the sensation of the moist tip kissing my hole. He did this again and again. Teasing my body for I moved closer at each pass. Then he looked into my eyes and slipped the head of his glorious penis into me.

I lost a breath as the tip opened my body slowly. "Ohh, ohh, Geor," as he inched inside so slowly I wanted to scream. Not from pain but desire, "Fuck me George NOW!"

He slipped a bit further in and than withdrew. "Is this what my girl wants? You want a cock to split your moist lips open Sara?"

"Yes, yes, " as he slipped inside me again but not all the way. He stopped, "Just enjoy that I'm so hard for you lover."

Again he withdrew. Taunting me he bent and licked my body, pushing his tongue into me, "Now I'll fuck you. I'll make you want you are. I'll open your body and push my meat inside you. I'll spray my seed into your body Sara."

He pumped in and out of my pulsing body for a whole two minutes before I screamed into his ear, "I'm cuming, Geor, I'm, I'm loving your cock George! Fuck me, ahhhh!!"

After we shower together I sucked him. "Do you want me to..."

"No George, not tonight. I want your cock to bring me to orgasm again, maybe three more times." He ran after me into the bedroom again.

Applying the third condom was difficult since he was so wet from my blowjob. I moved away a bit. He was behind me looking at my butt framing by the suspender hose'. Standing in my heels I moved toward the wall of glass overlooking the night sky. I asked him to come closer, his stiff dick pointing at me. I still wore my thong and bra.

"Can anyone see you Sara?"

"Who cares! It's three in the morning and I want your cock in me please."

He approached and simply entered me. I breathlessly received his thrusts as he pushed against my bottom, "Faster Please!!"

He paused after a minute and I turned around dropping to my knees. My mouth loved and licked George. He moaned but pulled me up and kissed me as he entered me again. At this angle it was not good but he shifted and it was less awkward.

"Lift you leg Sara to my arm."

So standing with my back against the glass and my leg held in the crook of this left arm he fucked me looking into my eyes.

"Is this how you wanted it a month ago Sara? Me deep inside you?"

Near dawn as he slept I walked about the stillroom with my hand cupped at my groin. His seed oozed from my body but I didn't want to waste it. I licked George's semen from my right hand as my left gathered ounces more of the sauce that had been inside me.

I did feel differently. After twenty minutes I climbed back into bed and kissed the cock that had been mine all night. Three times he had fucked me and I'd cum twice strongly but I needed more. His phallus rose slowly and I slipped the condom over the tip as moved to straddle his torso.

"Wants happening?"

He awoke to see me without my wig, my makeup a little smeared and my chest free, my breasts swaying over him. I pushed the thong panel aside and inserted him into my body and slowly I fucked him as I looked to his face. His eyes were closed and his mouth smiled at me.

He whispered, "Sara, your body makes me feel very good. You're so tight wrapped about me."

I moaned for his long cock was banging my prostate. I moved him in and out of my body. Twice he slipped free but I reached to push him back into my canal. After a few minutes I moaned deeply, "I'm, I'm cuming again, again George!" as I increased the tempo but this orgasm started differently from any other I'd experienced.

It was slowly building and building. Two minute later I was still fucking George and feeling the continuing rise of this unique orgasm. I pushed down atop his dick as I came and released into the thong but I felt contractions all over my body and these didn't stop. It was my first all body orgasm.

I no longer saw my new body as bad or wrong, just me, just Sara.

I quivered as I fell to his chest and he kissed my mouth. George was still deep within my body as new thoughts came to my mind. I was Sara and liked having a cock in my body, a lot. I wasn't in love. I knew now I could enjoy being with a man but I needed more experiences.

I thought of Angelica and I smiled, "Thank you, you big stud."

He continued to move within me as I realized he hadn't cum.

"We're not don't yet sweetie," he said and a minute later he shot within me again. I was somewhere else though.

I was thinking of Cynthia.

The End of part fifteen

To be continued . . .

MadQuill
MadQuill
358 Followers
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DaveXX80DaveXX80over 8 years ago
Still great!

15 chapters in and it is still a joy to read!

AnonymousAnonymousover 8 years ago
and annony. is like a asshole.

5 for content and a good read

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