A Second Chance at Love

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"Did she? That's very sweet of her."

"You didn't think it was amazing?"

"It was amazing. And she's an amazing person."

A couple of weeks later, the College President asked me to come by to discuss a legal matter. I arranged to have lunch with Shari after the meeting.

As I was leaving the President's office, he said he wanted to have quiet word with me about Professor Durning. "She's your friend, I believe," he said.

"Yes. I'm having lunch with her today."

"Good. Good," he said. "That's excellent. You know, dear boy, how colleges are a hotbed of gossip."

I said I did, fearing where this was going.

"And some gossip has reached my ears about Professor Durning. About her past. Do you know what I'm referring too?"

"I think so."

"Not necessarily malicious gossip. Just gossip. People believe they know things about her and want to entertain others with their discovery."

I nodded, waiting for him to continue.

"Well dear boy, it's not something that I feel it's appropriate for me to talk to her about. But you're her friend, and you might want to tell her that idle tongues have been wagging."

"Thank you," I said. "I will let her know."

"And tell her this as well, dear boy. I can't prevent gossip, but as long as I'm President, no-one will do anything to make her unwelcome here. She's a lovely girl and an outstanding teacher and the college is very lucky to have her teaching here. Do tell her that, my boy. Tell her that I'll do my darndest to make people know that she's very welcome here."

I shook his hand and left.

I met Shari at the Italian restaurant on Main Street. I had been coming here for years, and the owner met me with a big embrace. I introduced Shari. As he led us to the table, I exchanged greetings with a half dozen people eating there.

"Do you know everyone in town?" she asked.

"Not everyone," I said. "But enough people that it'll be all over town by this evening that we had lunch together."

I told her about my conversation with the President. "It had to happen," she said. "The academic world is so small. Someone who knew me in Berkeley would have spoken with someone here or someone who knows someone here. I never thought it would remain a secret. But his words are reassuring. He's a decent man."

"He is. And he's also very savvy."

"How so?"

"The College prides itself on being liberal. Kids come here for that reason. He's not adverse to it being known that the college has faculty with unorthodox backgrounds."

She laughed. "Unorthodox backgrounds! Such a wonderful way of making me sound deviant. Is that why you didn't contact me after that night?"

"Perhaps. I don't know. I wanted to, very much. But each time I was about to I didn't go through with it."

She put her hand on mine. "It's ok, really it is."

"No, it was wrong of me. I was too young to realize that what had happened between us was so wonderful."

"And now? Do you feel deviant being seen with me?"

"No. It feels incredibly natural."

"Not even a little bit deviant? After all, everyone in town will know that you were holding hands with a girl with a cock."

I smiled at her. "Ok," I said, "a little bit deviant."

"But in a nice way?"

"A very nice way."

Seven

A couple of weeks later, Shari texted me to say that Diana had invited her for Thanksgiving. I called her.

"That's wonderful," I said. "Are you going to go?"

"I'm thinking about it. I'm a little nervous. I haven't been back to town since I became Shari."

"Maybe that's good reason to go."

"Maybe. But I also wanted to make sure that you're ok with it."

"Of course I am. Why wouldn't I be?"

"Because Diana is so keen that we get together that it might be awkward for you."

"So she's working on you too. I think we can manage it. It'll be great for you to be there."

"Really?"

"Yes, really. But be prepared for a household full of kids insisting that you play with them."

"I can deal with that."

"Don't be so sure about it. But if it gets too much we can run away together."

"I'll keep my bag packed, just in case."

Thanksgiving morning I picked her up at her apartment and we drove the three hours back home. She was quiet during the trip, and I sensed she was nervous.

"When were you last here?" I asked when we got close to town.

"The summer after my first year at Berkeley. My parents had sold the house and were moving to Florida and I was helping them pack up. I was still Steven at that time, but at the end of the summer I told them I was thinking about making the change to Shari."

"How did they take it?"

"Surprisingly well. I guess they had always known that I wasn't really a normal boy. They had lots of questions about the process and the like, but told me I should do it if I had decided that's what was best for me."

"Do you see them in Florida?"

"A couple of times a year. The first visit after I became Shari was a little odd for all of us. But it's wonderful now. My mom loves taking me to meet her friends and seeing their reactions."

"How do they react?"

"I sometimes notice those that know about me scrutinizing me when they don't think I'm looking. But maybe that's because mom asks me to wear short shorts and a skimpy top when we go visiting. It increases her fun, so I'm happy to oblige."

I looked at her and smiled. "You should dress like that next time we go out for dinner."

"And get the sluttiest professor of the year award?"

"Hey, if it helps you get tenure, go for it."

"And there was me thinking that I would get tenure because I'm David Harris's friend."

"I'll put in a good word for you. But I still think the shorts might help."

Diana and her husband and three kids made a big fuss of us when we arrived. As soon as we got through the door, the kids started insisting that Shari come play with them.

"It's started already," I whispered. "Let's run away."

"Too soon," she whispered back. "It might be thought rude."

Diana had given Shari the spare bedroom. Whenever I went back for Thanksgiving I stayed at a nearby hotel. "But there's a king size bed in the spare bedroom," Diana said to me, outside of Shari's hearing. "You could stay with Shari."

"Sis," I said, "you promised no matchmaking this holiday."

"Ok, ok. But I had to try at least once."

We ate dinner and hung out with the family, and I went to the hotel about ten o'clock. I texted Shari. "All good?"

"All good" she replied. "Sitting talking with Diana."

"Call me before you go to sleep," I wrote.

"Will do," she replied.

She called an hour or so later. "Guess what Diana put on the bed for me?"

"I can't imagine."

"The white shirt. The one I wore all those years ago."

"The very same one?"

"It looks identical."

"So you did tell her all the details!"

"I had to tell her she was right about the effect of a white men's shirt."

"Did you put it on?"

"Yes, of course. And it looks even better now I have boobs."

"Wow," I said. "I bet it looks amazing."

"Here, you can see." A picture arrived on my phone. She was lying back, her head on the pillow, and the top buttons of the shirt were undone, exposing the top of her small breasts. The bottom of the shirt reached down to the top of her thighs.

"So, so beautiful!" I said.

"I'm happy you like it. Sleep well."

"You too. Sweet dreams."

Eight

My high school class always had a meet-up at the school football field the morning after Thanksgiving. We drink coffee and eat cookies and catch up with at everyone is doing. Usually there's a game of touch football.

"You will come, won't you?" I asked Shari.

"But it's not my school class," she said.

"That doesn't matter," Diana said. "I always go. Gossip is gossip, even if it doesn't come from your own classmates."

"And everyone will tell their brothers and sisters that they saw you," I said. "It'll be like a rare sighting of a mysterious phenomenon."

"Like bigfoot?" Shari asked.

"I was thinking more like an exotic animal, like a snow leopard."

Diana put her arm around Shari's shoulder. "It'll be alright," she said. "David and I will be look after you."

Diana and her husband and kids and Shari and I squeezed in Diana's car and we drove to the school. Shari was wrapped in a too-big duffle coat she had borrowed from Diana.

"I feel more like Paddington Bear than a snow leopard," she said.

"You look adorable," I said.

"I should be carrying a jar of marmalade."

We walked to where everyone was gathered around the coffee and cookies, and spent the next hour milling around, chatting, exchanging news. Diana, being Diana, had left nothing to chance. She had told her girlfriends that Shari was going to be there and her girlfriends had told their husbands. She introduced Shari in a direct way. "This is Shari Durning. She was Steven Durning when she was at school with us." I saw Shari gradually relax as she realized that she was among friends. I smiled at her and silently mouthed "All good?" She smiled back and nodded her head.

I left her with Diana and went to join the game of football. These were guys I had grown up with and played football with for decades, and away from their wives they were less reserved.

"Your sister's friend is so hot."

"If you get boobs, why not get huge ones?"

"Does she still have a cock?"

"I'd do her even if she did."

We played for an hour or so until it started to rain. I walked to where Shari was standing on the sidelines with Diana and the kids, all sheltering under umbrellas. Shari lifted her umbrella up to shelter me from the rain. We stood there, close together under her umbrella, looking at each other, smiling. She looked adorable beyond belief. Then we kissed, a soft lingering kiss.

"Uncle David is kissing Shari!" one of the kids shouted. The other kids took up the shout. "He's kissing Shari." I heard cheers from all around, and a few whistles. We kissed again. I took Shari's hand and we walked back to the car. I went to the hotel and showered and changed and checked out, then drove back to Diana's house. We hung out with the family until late afternoon, then said goodbye and hit the road.

I saw Diana whispering in Shari's ear as we said goodbye. "What did Diana say when we left?" I asked.

"That it's so romantic that we're together and that we make a beautiful couple."

"She's right," I said. "It is totally romantic, falling for the woman I first fell for when she was a boy."

"And she gave me a present."

"What is it?"

"The white shirt."

Nine

When we arrived back at the college, I parked outside Shari's apartment. She looked over at me. "You are coming in, aren't you?" she asked.

"Yes," I said.

I carried her bag into her apartment. We stood looking at each other for a few seconds. Then she stepped towards me and kissed me on the lips. I put my hands around her waist and pulled her close, feeling her small breasts press against my chest. We kissed again, deeply and passionately, and my cock grew hard with her touch and her kisses. Then she took my hand and led me to her bedroom. She opened her bag and took out the white shirt.

"I'm going to the bathroom to put this on," she said. "I want you to undress and get into bed."

"Like last time," I said. She smiled at me.

I undressed and got into bed. After a couple of minutes Shari came out of the bathroom dressed in the white shirt. She sat cross-legged on the bed, facing me, and folded back the duvet and looked at my naked body. My cock jumped, yearning for her touch.

She undid the top three buttons of the shirt and folded it back so I could see her breasts. Sitting beside me, half naked in the white shirt, she was beyond beautiful. She took my cock in her hand. I gasped with the rush of pleasure racing throughout my body. She slowly stroked my cock, looking at my face, smiling at me. With her free hand she undid the remaining buttons. I stared at her slim body, her little breasts, her hard cock. I took her cock in my hand, hearing her sighs. She leaned over and held my cock against her chest, rubbing it against her breasts as she stroked me. "Ever since I got boobs I've imagined undressing for you," she said. Feeling her touch, seeing her naked body, hearing her moan, my orgasm grew, slowly, slowly, as from deep inside of me. Her grip on my cock grew harder, her strokes firmer. She looked at me with her sweet smile, watching my face as my excitement reached its peak and I came, a huge shuddering crash throughout my body, a long spurt of cum splashing over her breasts, then another, and another.

As my orgasm subsided, we looked at each other, neither speaking. She let go of my cock, and with both hands rubbed my cum over her breasts. I held her cock, watching her play with her breasts, watching her gently pinch her hard nipples, seeing the excitement on her face. Her little cock fit tightly in my hand; each movement of my hand enveloped her whole cock. I sat up on the bed and kissed her as I stroked her cock, our mouths and tongues pressed together. "I've thought about this so often," she sighed. "You kissing me, making love to me." She rested her head on my shoulder. I heard her breathing get deeper as I stroked her cock. "Baby," she moaned, "I'm going to cum." Her body tensed and her moans got louder and longer. I felt her cum splash over my hand.

We lay back on the bed, her head still resting on my shoulder. She kissed my cheek, and I turned to look at her. We kissed softly.

"That was amazing," she said at last.

"As amazing as the first time?" I asked.

"Nothing will ever be that amazing."

I kissed her. "I've always felt a little bad about that night," I said.

"Why?"

"Because you had had such a bad time that evening. I felt I might be taking advantage of you."

She laughed. "Baby, it was the other way around. I was taking advantage of you. I instigated it, remember?"

"I remember. But still, maybe I should have put up more resistance."

"I knew what I was doing. I knew what I wanted. You had been so sweet. And I had had a crush on you for the longest time."

"Really?"

"Yes, really. One day I was at your house doing homework with Diana, and you came back from running. You were wearing just a pair of running shorts and you were covered in sweat. I suddenly had a vision of licking the sweat off your naked body."

"Wow!" I said.

She laughed her sweet laugh. "Diana saw how I was looking at you and dragged me away before I embarrassed myself."

"So I have my sister to blame for not getting to know you years ago."

"You would have been so embarrassed too. I don't think the school's star football player would have welcomed my attentions."

"You're right. I wouldn't have known how to deal with it."

"And now?"

"And now? I feel like I'm the luckiest person in the world to be lying here with you."

We lay together in silence for a while.

"That night," she said, "I thought I would risk it. I thought that you probably wouldn't rebuff me."

"A calculated seduction?"

"I thought the odds were in my favor."

"How could I say no to a beautiful girl asking to get into bed with me?

She was quiet for a while. "That night, did you think of me as a girl?"

"Yes, from the moment you came through the door."

Shari took my cock in her hand again. "I felt like a girl for the first time," she said. "You holding me close, and kissing me." I was hard again.

"But I have one regret about that night," she said.

"Oh no," I said. "What?"

"I wanted you to fuck me but was too shy to ask."

"And now?" I asked.

She smiled at me. "Will you please fuck me David?"

"Well, Shari, given that you ask so politely —."

She straddled me, and lowered herself onto me very slowly, then began to raise and lower herself on my cock. She took my hands and put them on her breasts. "Squeeze my nipples, baby," she said. Each time she lowered himself onto my cock her face came close to mine and we kissed. We got into a rhythm of my cock pushing into her, me squeezing her nipples with each thrust, and our mouths meeting. It couldn't last long. Each thrust made me closer to cumming, but I wanted her to cum first. I put my hand on her cock, squeezing her firmly in time with each thrust of my cock. Her sighs became one continuous moan and then a loud cry as she came. I pushed more deeply into her and came too, pressing hard against her as my cum shot into her, spasm after spasm.

She lay on my chest, her head on my shoulder. She kissed my cheek. Our phones beeped in unison. "Diana," we both said.

Shari reached for her phone and read Diana's text. "Are you guys good? You left so early. I wonder why?! I want to hear everything!"

"Do you get the impression that my sis gets turned on by the thought of us together?" I asked.

"Would that be so bad?" she said. "What we just did was pretty hot."

"So you'll tell her?"

She typed a reply to Diana.

"What did you say?" I asked.

She read her text to Diana: "The white shirt worked its magic again. Details later."

"You're really going to tell her the details?"

"I'll spare her the really, really, kinky ones."

"Have we done anything really, really, kinky?"

"Maybe not yet. But you are staying the night, aren't you?"

"Yes," I said. "And tomorrow I want us to go for brunch to the busiest place in town so everyone can see us together and guess that we'd spent the night doing kinky stuff to each other."

"Sounds wonderful," she said. "That'll give me a lock on tenure."

"That and going to the football games."

"You'll buy me a camel scarf?"

"Of course."

"And you'll tie me up with it and do kinky things to me?"

"After every football game we win."

"And if we lose?"

"You tie me up and do kinky things to me."

She held out her hand for me to shake.

"Deal," she said.

I took her hand and pulled her close to me. "Deal," I said, and kissed her on the lips.

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jinyx_xeijinyx_xeiover 1 year ago

This was so great, less emphasis on the sex and more on the connection between characters. Very romantic, please write more 💜

AnonymousAnonymousover 1 year ago

This is my favorite kind of story. The sex is natural and the intent of the characters toward one another is sweet. I get so tired of filtering through all the stories of people dressing up and searching out strangers in movie theaters. I enjoy the romance. David and Shari were so sweet with one another.

Charlene99Charlene99over 1 year ago

Very sweet story very well written. Thank you!

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