Olivia: A Love Story

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A Transgender Love Story.
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I remember the weekend like it was yesterday. A good friend from university was getting married and I was surprised since I never thought of Harry as the marrying type. He had multiple girlfriends in school but now in our mid-thirties, one obviously was able to tame him. I received an invitation and was tossing around the idea of attending the wedding when I was invited to his bachelor party and suddenly felt obligated.

Harry confided in me that his bride to be came from a very well-connected family and were quite wealthy.

"That's why you're getting married?" I asked with skepticism.

"Nah, well I mean it helped, but I'm in love Jason. I guess there's a first time for everything."

"You're, 'love em and leave em' Harry? I'm shocked."

The affair was at a very ritzy venue in Center City Philadelphia, and everything reeked of opulence and taste. Although I was permitted to bring a guest, I decided to attend as a single or stag.

Since my divorce, I'd been dating sparingly, not that I was picky. Shannon, my ex, remarried a year after the ink was dry on the paperwork. We'd been married for twelve years but the last one was rocky. I suspected infidelity but couldn't prove anything. The divorce was amicable, no children were involved, I kept the house and bought out Shannon's half.

It was during the cocktail hour when a dear friend, Rhea Falco was at my elbow. She was part of a group from our university days that socialized once a month. She taught at the University of Pennsylvania and was the group match maker. I loved her as a friend, but she couldn't stand to see anyone single.

"There's someone I want you to meet. I know she'll be here and I'm dying to get you two together."

"Rhea, I appreciate your efforts but I'm enjoying being single."

That was a lie because I loved being married and sharing my life with someone.

"Nonsense Jason! No one should be alone and you're a good catch."

I grumbled but Rhea was having none of my attitude.

"Ooh, here she comes. Now I want you to be nice and charming. Ok? Promise?"

"Yes, I promise." I said halfheartedly.

"Jason Whitson, I'd like you to meet Olivia Stansfeld."

I turned and looked at one of the most beautiful women I ever laid eyes on. Her chestnut hair cascaded down her back and the dress she wore hugged her figure like a glove.

"Hello, Jason, it's a pleasure."

"Sss...ame here." I stuttered.

I was blown away by this goddess in earthly form.

"I'll see you two later..." and Rhea made a hasty exit.

"Can I get you a drink?" I asked bashfully.

"Champagne would be nice."

Olivia's voice had a sultry quality like Jessica Rabbit.

As I handed her the champagne flute, I appraised her look. While her voice was reminiscent of that famous cartoon character her body was not. Her svelte figure was a sight to behold. I'm a sucker for sleek, hard bodied woman and she fit the bill perfectly. Her face was framed by that lovely chestnut hair I first saw, soft brown eyes and pert nose. Olivia's arms and legs were perfectly toned.

"So how do you know Rhea?" I asked.

"Oh, she works in the department next to mine at the university, we share the same secretarial pool, so we run into each other occasionally. She's a dear woman but recently she found out I was single and..."

"Yeah, I know. Rhea wants to see everyone married." I said wistfully.

"I take it you're here stag?" she asked with smile.

"Yep, and I'm thinking you are too, but I don't know the female version for stag."

Olivia chuckled and the smile never left her face. I've never been a great small talk conversationalist and there were a few awkward pauses until...

"What did you think of the wedding ceremony?" she asked.

"As far as wedding ceremonies go, it was typical, but I always envision something more chaotic like the classic film, "Father of the Bride"."

Olivia almost choked on her champagne.

"I love that movie! You're referring to the dream sequence with Spencer Tracey."

Well, dear readers, like the line at the end of another classic film, "Casablanca", it was the start of a beautiful friendship. We spent the rest of the wedding talking about classic film and our love for Turner Classic Movies or TCM.

Thankfully we were seated at the singles table and rearranged the cards so we could sit together. The wait staff was cleaning up before I realized the reception was over.

In a just a few hours, I'd grown fond of this beautiful creature. She was erudite, charming, intelligent, and fun to be with. Her enthusiasm was infectious, and I was falling under her spell.

"Olivia...I'm not good at this sort of thing but would you care to have a drink with

me at Cagney's, it's not far from here."

Cagney's was a pub style place with movie memorabilia plastering the walls.

"I'd love too but just one, I'm driving."

"I took an Uber, give me sec and I'll call..."

"You can come with me. I don't bite..."

Her comment made me chuckle.

"Sure, that'd be great."

Cagney's was full but we found two seats at a high-top table. I ordered a beer and Olivia a virgin daquiri. I couldn't help staring at this very pretty woman. She was on the tall side, five nine or ten, as tall as me in heels. The subject of our conversation seemed to delight her but soon we needed to change the topic.

"So, what do you do for a living?" I asked.

"I'm a professor at Penn. I teach Engineering. It sounds lofty but it's not. My father was an engineer and I guess the apple didn't fall far from the tree. How about you?"

"I'm an attorney. I handle mostly bankruptcies, some litigation. It's nothing to write home about but it pays well."

Those kinds of exchanges can be stifling but somehow the conversation steered back to classic films and we off to the races again. We were discussing a charming film with Cary Grant and Myrna Loy called "Mr. Blandings Builds His Dream House" when we heard last call from the bar.

"Wow, look at the time..."

When Olivia pulled up at my home, I felt sad that the night was over. I don't know how but I summoned the courage to ask Olivia for a date.

"Saturday night about seven?"

Olivia had a sparkle in her eye that said she was going to accept and, she did. I promised to call her to finalize it and practically skipped up the driveway.

On our date, Olivia looked radiant, dressed impeccably and thankfully she wore flats. She talked about her love of teaching and had some hilarious stories to relate.

"So, Jason, why is a good-looking guy like you still single."

"Thanks for the compliment but anyone would look better seated across from you."

Olivia blushed.

"You're quite beautiful." I gushed.

"Thank you so much but if you saw me without makeup and in sweats, I think you'd feel differently."

"I'll bet you make them look good too."

"Enough about me..."

I talked about my marriage to my ex-wife, Shannon but not in a derogatory way.

"I'm not sure what happened, the first eleven years were good but the last one...it was a steady decline. One day, she asked for a divorce, and I saw little reason not to at the time. I haven't dated much the last couple of years. Just haven't been looking hard enough I guess."

"And why are you still single?" I asked jokingly.

Olivia was very thoughtful.

"I'm not sure but...I don't have a solid reason..."

Olivia looked uncomfortable with my question; it was good time to call a retreat.

"Hey, I didn't mean to put you on the spot. You don't have to answer but, and this is not one of those bullshit lines, I would think someone as beautiful as you would have been snapped up years ago."

Olivia blushed a little, but I could tell she was impressed.

Our food came and it put a brief halt to our conversation. Since I was driving, I drank no alcohol, but Olivia only had one glass of wine with her meal. After we begged off dessert and we're drinking our coffee's, another stroke of luck. Olivia looked at her phone.

"I'm headed up to Adamstown, near Lancaster tomorrow. I love to go antiquing at the outdoor markets."

I think my eyes bugged out and I sputtered my coffee.

"I'm a huge fan of flea markets. My ex and I went at least once a month in warm weather. But since my divorce I don't know anyone that's interested. I'll go stag occasionally."

Olivia chuckled.

"Oh, I used that word again, stag..."

"Jason, would you..."

"Yes, I would most definitely."

"Great! I'll drive and pick you up at six?" Too early?"

"Heck no!"

When I dropped Olivia off, I walked her to her door. Before I could say goodnight, she pulled me in for a hug.

"Thanks for a fun night, Jason. See you tomorrow morning, early." She sang.

I barely slept that night, afraid I'd oversleep. Promptly at six, Olivia was in my driveway and off we went. We chatted about what we liked to collect. Olivia collected glassware, mostly Depression and just about anything for an elegant table setting.

We spent the morning combing through several markets, occasionally stopping to get a coffee or a breakfast sandwich. By noon, we were ostensibly done and talked the whole way home about the treasures we found. Olivia invited me into her home for the first time and it was impeccable like her, decorated in period antiques as well as modern.

She had two entire China cabinets filled with glassware and showed me her prized pieces. I was thoroughly impressed, and she was gazing at me with an affectionate expression.

"You're a dear for listening to me go on and on."

"Oh no, I loved listening to..."

The next thing I knew, I was in Olivia's arms, and she was hugging me enthusiastically. There was a genuine fondness between us, I could feel it. Before I left, she invited me to dinner and swim at her home Thursday evening. Of course, I agreed and spent the week in nervous anticipation for what lie ahead.

Thursday, I was at her door by six with a bouquet of flowers. She answered in a silky robe, and it clung to body seductively.

"Patio's that way. I'm gonna quickly change into something more appropriate."

When Olivia walked out to the patio, I quietly gasped. She was wearing a print and aqua color bikini, the top fit her like a glove. Her lower half was covered by a mid-thigh sarong, and I was hoping, she'd remove it at some point so I could get a gander at the entire package.

"How do you like your steak?' she asked in that sultry voice that sent chills down my spine.

"Oh, medium rare..."

Olivia put two large Filet Mignon on the grill.

"Is there anything I can do?"

"I like bourbon with my steak, lots of ice in the glass. I have a bottle on the picnic table."

I looked and sure enough there were glasses and an ice bucket but what really caught my attention was the brand of bourbon.

"Wow, McKenna's! You have good taste!"

"I don't drink very often but when I do, I prefer the good stuff. And it goes great with charred meat."

When we sat to eat, I couldn't take my eyes off her, especially her breasts. They weren't big but beautifully shaped and the nipples poked the thin fabric. Of course, she caught me.

"You like looking at me."

"Yeah, sorry...I'm sorry."

"Don't apologize, it's very flattering but your steaks getting cold."

I dug in and with every piece I stuffed in my mouth, I took a sip of spirits.

"Olivia, you were right. The combination of the steak and whiskey is spot on!"

"Thanks, I don't get many opportunities to cook for someone, so I'm glad you're enjoying it."

We mostly ate in silence, but her last comment had me wondering.

"I can't believe that men aren't beating down your door to spend time with you. You're incredibly smart, talented, and beautiful. You're the complete package."

Olivia blushed deep crimson.

"Thank you, Jason...I don't hear compliments like that very often, in fact almost never..."

I saw a shadow of sadness move across her lovely visage. As I helped Olivia clean up, I refreshed our glasses.

"Just one more...I can get very tipsy..."

"Afraid I'll take advantage of you."

Again, I saw that shadow of sadness, of hurt in her eyes.

"Hey, I...ah...forget what I said...I feel like I'm offending you."

"No, please don't mind me...it's just...no one's been this nice to me in a long time."

We sat quietly on the edge of the pool, our feet in the water.

"Can I put my arm around you?"

"Yes, certainly..."

As I put my arm around Olivia's shoulder, I realized she was shaking.

"Are you cold?"

"No, just...a little nervous."

I couldn't help myself, leaned over and tenderly kissed her very soft cheek. Olivia responded by laying her head on my shoulder.

"Thank you, Jason. Thank you for being here with me."

When Olivia looked up at me, there were tears rimming her eyes. She threw her arms around my neck and kissed me with passion. I was blown away by her supple lips.

"I wanted to do that for quite some time." She said shyly.

Wow, the girl knew how to kiss.

I held her close and whispered in her ear,

"My god, that was amazing."

Olivia pulled me to her, and I could feel the points of her nipples against my thin shirt. We made out like two horny teens on date night, and I found her bourbon scented breath, incredibly arousing. My cock was so hard, I thought it would split the front of my swimsuit. I wanted Olivia like no one else I'd been with, including my ex-wife.

But instinctively I knew I would have to take it slow with her. Somewhere along the line, Olivia had been hurt and hurt badly, by someone or more than just one.

It was past twilight when we finally stopped. The glow of the candles on the table added a warm touch to the atmosphere. I held her close, cheek to cheek, reveling in the touch of her bare skin, the warmth of her body. It was beautifully romantic, at least for me.

"Hey, I should be going...we both have to work tomorrow."

"Yeah, I have an eight am class. I just love seeing their tired, bored faces that early."

Olivia snickered.

"You really like teaching, but it must be challenging at times?"

"Truthfully, I love teaching and it can be difficult but also, very rewarding."

Olivia looked very thoughtful.

"Jason, I don't mean to be forward, but will I see you again?"

"Yes, absolutely...why would you think the opposite? Can't you see that I...I'm smitten with you?"

"I feel like I'm playing "hard to get" but I have my reasons."

"Look, Olivia tonight was one of the most romantic evenings I've had in a very long time. There's no timetable. I enjoy being with you immensely and I feel lucky that a woman like you would...find me...appealing. Plus, you're a damn good cook!"

Olivia snickered but her sudden tearful gaze had my heart thudding in my chest. We stopped at her front door, and I wanted to say something, but my voice failed me. She put her hands on the back of my neck and pulled me in for some very intense kisses. My hands dropped to her very firm derriere and gently squeezed.

Olivia gasped but kept right on thrusting her sensuous tongue into my mouth, Frenching me like no other. My erection was back and hard as blue steel! It was grazing her lower abdomen.

"Is that because of me?" She asked knowing very well that it was.

"I don't see anyone else here." I said looking around with a comic face.

"I guess we'd better stop..."

"Can I call you tomorrow? When are you between classes?"

"Yes, I would love for you to call me and I'm free between eleven and twelve thirty. I eat lunch at my desk."

I drove home insanely infatuated with Olivia Stansfeld. In the shower, I choked my chicken fantasizing what sex with her would be like, until a titanic squirt of cum splattered against the tile wall. It was downright voluminous.

Unable to sleep, I lay in bed lost in the warm, romantic feelings that I had for her. I'd never met anyone remotely like her. But one thing bothered me, why would this fantastic woman have any interest in me. She could have the pick of the litter. I thought my ex was beautiful, but Olivia easily put her to shame.

My ex always told me I was too hard on myself. I put the hours in at the gym to maintain a lean muscular look, nice six pack abs and my best features were my arms and shoulders. My biceps and triceps had real pop thanks to my trainer.

As far as my looks? Well, over the years I had no problem attracting the opposite sex but Olivia, in my opinion, was out of my league. Also, there was something I couldn't put my finger on, something I was missing.

When I called Olivia the next day, she picked up after the first ring. She must have been waiting for me to call her. We talked for bit, but I wanted to ask her out for another date. The local cinema was having a one night showing of the classic romantic comedy, "Some Like It Hot"

When I told her the film title, she jumped at the chance to see it in theater.

"Love it! But I buy the popcorn, deal?"

"Deal!"

When I picked up Olivia, I marveled at her taste in clothes. Jeans that fit her sleek build to a T and a classy Polo that hugged her chest. The sandals on her feet were the perfect complement to the package. This beautiful woman was positively radiant.

Olivia bought the popcorn and ate it with an elegant flair. The way her long fingers, held a piece or two had me fantasizing having them wrapped around my cock. But I did my best to dispel those thoughts.

During the movie, I put my arm around her, and she snuggled against me, resting her head on my shoulder.

"That film is a true classic." Olivia said with laughter as we walked out of the theater.

"Yeah, I love the last line, 'nobody's perfect', kills me every time. It's so different seeing it in a theater, it just adds another dimension you can't get at home."

"It's nice to know you weren't bullshitting me. You really like classic films." She said with a broad smile.

"Well, TCM is one of my favorite channels"

Olivia took my hand and held it with a fond look in her eyes. There was an elegant little bistro a short walk from the theater, and we stopped for a quick bite. I wanted to buy her a drink, but she insisted I get one instead.

"I'll be the designated driver. You indulge, ok?"

"Thanks, your very kind." I said softly.

I ordered McKenna on the rocks and Olivia reached across the table and took my hand. As I looked into her sparkling brown eyes, I basked in her glow. She exuded more than sexuality, there was so much more about her. Her wit, intelligence, the way she carried herself with grace and confidence; always impeccably dressed to suit the occasion. She had this down to earth way of talking and communicating that made me feel comfortable in her presence.

Olivia was telling me about one of her students and the smile on her face could have launched a thousand ships like Helen of Troy. I was enthralled and had fallen under her spell. In a short period of time, I had become her slave, I'd do anything she asked of me.

In the car, she took the driver's seat but leaned over and kissed me.

"You really like me, Jason?"

"I more than like you...ah..."

Damn! It slipped out before I could think. Olivia gazed at me with something more than affection. With her hand behind my neck, she aggressively thrust her tongue in my mouth, and we were Frenching like mad. I felt a hand drop to my lap and very gently fondle my raging hard on. She did it with such delicacy; feeling, clutching, and stroking until I couldn't hold back my impending orgasm. A mini--Mt. Saint Helens erupted in my civies.

"Oh shit!" I gasped.

Olivia was temporarily confused but slowly a wide grin enveloped her face.

"Did you...?" She asked with a smirk.

"Yeah..." I responded sheepishly.

Olivia covered her mouth with her hand and chuckled in a sexy way.

"I like having this effect on you! Makes a girl feel...oh, proud. I guess I better get you to my house so you can take care of business."

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