Olivia: A Love Story

Holidays were extremely rough when I'd get boy gifts and he'd make snide comments. They didn't go unnoticed by my mother, and she was aware of my very rocky relationship with him. Playing sports kept me out of the house as much as possible and I usually hid in my room when I was at home.

One Saturday when I was thirteen, my stepdad was away on a fishing trip with his equally macho buddies. I came home after soccer practice and was overjoyed he wasn't there. My mom was making homemade pasta, a long and arduous task. I volunteered to help. Now, I always helped her cook and prepare food for meals.

But this day, she was unusually quiet. I'd always kept my feelings a closely guarded secret and the only person who knew was my sister, who I'd sworn to secrecy. But I later found out, Cheryl spilled the beans about me and what my stepdad was like when my mother wasn't around. Because he was verbally abusive, she felt duty bound to tell my mother. Later when I confronted her, she told me point blank that I had suffered enough.

Now, I'm sure my mother had her suspicions about me, like why my boy toys always looked brand new, many still in the box. Why I preferred looking at fashion magazines and any magazine with a female emphasis, Cosmopolitan for instance. Also, my choice of TV programs tended to be female oriented.

With a little prodding, I poured my heart out to her. There were lots of tears by both of us and for the first time I felt some relief. When my asshole stepdad came home from his fishing trip, she made him move out and divorced him. My mother was a lawyer and a pretty good one, I don't think he got much in the settlement.

My second stepdad was the complete opposite. A kind, caring and loving man. We got along famously, and he was so supportive. After a year of calling him Walter, I asked if I could call him, dad. He cried because he never had any children of his own. For the first time, since my dad's passing, I felt a father's love.

My high school years were semi-normal. I kept my feelings to myself and poured my efforts into sports and schoolwork. But after I turned eighteen, it was extremely hard to hide my attraction to men. My first year at college I was beaten up a few times and a friend suggested kickboxing.

At the end of sophomore year, my mother passed away. I was heartbroken but in her will she left Cheryl and I a significant inheritance. Mine stipulated that I would receive a lump sum when I turned twenty-one with the rest put in a trust that I could draw on yearly.

It was then that I decided to transition. I'd read a lot about it and knew that it was what I wanted. After I graduated college, I started the process. My girlish, pretty boy looks turned me into a pretty female. I loved the way I looked, and I pursued doing everything as a female. Oliver became Olivia.

But dating was a nightmare and even with my extensive kick boxing training got my butt kicked and heart trashed a few times. While that was going on I concentrated on grad school and pursuing a doctorate. I love teaching and thanks to my mother, I was able to pursue that dream.

My dating history made me very cynical. I'd cried so much in those traumatic years that I thought I had no more tears to shed, that is until you came along.

When you cry because you love me, it makes my heart soar with joy. Life is worth living. I found tears that I thought had dried up long ago. Anyway, that's the Readers Digest abridged version of my life story."

Damn! I started crying and Olivia held me tenderly, kissing my forehead and cheeks.

"Don't cry, my love. You've made me so happy."

Because my tears made me feel like a first-class wussy, I stopped and looked down Olivia's sleek body. Except for her equipment, she looked amazingly feminine. Her beautiful cock lay seductively across her thigh. She saw me looking.

"I like having a penis and I don't know why. It's the one part of me I don't want to change."

Olivia tussled my hair affectionately.

"Oh, and I love watching you suck on it. You have this intense expression, like it's the best thing in the world!"

"It is." I said bashfully.

"Wanna go for a swim? I put the heater on this morning, should be nice and warm."

"Yer on!" I yelled.

I was already in the water when Olivia came out in a shiny navy-blue bikini that fit her like a glove. There was somewhat of a bulge between her legs but not overly noticeable. I asked how she managed it.

"It's a practiced tuck job. Not very comfortable but it makes me feel more feminine."

Olivia noticed I was grinning from ear to ear.

"You look very happy Jason."

"I am. Like you, I haven't felt this good in a long time. You light up my life!"

"Oh, how corny, like that treacly song but since its coming from you, well...you do the same for me."

We swam and cavorted like two kids, all touch feely at times. When Olivia went to the shallow end the bulge in the front was rather pronounced. She saw me looking.

"You have that hungry look, my love."

"Yeah, but you did promise me deepthroat practice this afternoon." I said like a bad boy.

"Yes, I did." She sighed.

We were in each other's arms, hungrily kissing.

"There's nothing better than having my lover worship my penis for an entire afternoon." She said wistfully.

"Ooh goody!" I said like a brat.

"You naughty boy! What am I going to do with you?" she sighed.

"Love me?"

"That's a given my love. That's a given."

We showered to get the chlorine off our bodies. In her bedroom Olivia positioned me much like she had when she deepthroated me. Surprisingly her lovely appendage was limp, and I gently held it, feeling its warmth. It was lovely beyond words. If someone wanted to design the perfect circumcised cock, this was the real-life model.

"It's beautiful..." I sighed.

Tenderly I kissed the head and shaft as it started to thicken. My kisses turned to licks making Olivia groan. Steadily the shaft engorged with blood to full erection, and it looked like a mighty missile ready to blast off. My lips and tongue coated the steely shaft with saliva.

"I'm glad you decided to keep this delicious tube steak. All I want to do is suck the sperm out of it!" I groaned yearningly.

"Yes, my love. Yes!" Olivia yelped her approval.

And with that, I hungrily gobbled her stiff pole, tongue lashing the sensitive V. I cradled Olivia's big balls in my fingers, feeling their weight.

"I can't wait to drain every drop from these..."

"Oh god, my love!"

I attacked her penis, gobbling like a madman. But I did remember that this was a lesson, especially when the head bumped my throat.

"Try to push it in, you'll gag but you'll have to fight the reflex."

I did and immediately gagged, coughing around her cock. I suckled for a bit.

"Now try it again, this time when you push, swallow, sometimes that will draw the head in."

I complied with the same result, sputtering but I kept trying and Olivia was patient and encouraging.

"That's good my love, keep it up. Eventually you'll get it."

I lavished her hard, thick tool with very wet licks, up and down the smooth shaft, twirling my tongue around the head. Again, I sank down until the head bumped my throat. Grasping Olivia's firm slim hips, I pushed forward more aggressively, and the head slid in for a very brief second before I coughed. I repeated the process several more times, but I was tiring. With my lips and tongue, I worshipped her glorious tool, until saliva was dripping off her sac.

My beautiful girl was panting.

"

I'm getting close..."

I smoked her hard pole, tongue swirling around the head until I detected it swelling.

"Oh...oh...oh...here it comes!"

A strong twitch and a copious jet of nut jam splashed my tongue. From my limited experience, I knew to swallow as more spurted in. It was less volume than her first orgasm but still satisfying and I swirled my tongue through her sizzling load.

Olivia's hand was on my back.

"Come on Jason, let me see you swallow my sperm."

I turned my head halfway and gulped the searing batter. Tenderly, I caressed her awesome testicles, proud that I had drained them.

"My god, I can't remember getting better head. That was well...phew...intense."

Olivia held her arms out as I turned and fell into them.

"My beautiful man, you tried so hard. I thank you and my penis thanks you."

I sighed heavily and didn't respond to the James Cagney reference from "Yankee Doodle Dandy."

I snuggled against my goddess.

"Did that tire you out?"

I nodded.

"Rest for a while. You really emptied my balls."

Olivia was holding me in her tender embrace, kissing the top of my head. My eyes were half shut and I was gently playing with her very limp penis. I was curious about her last statement because every morning I saw her take the meds that kept her looking feminine.

"Olivia, your body produces a decent amount sperm...I'm wondering how...since you take male suppressing hormones."

"I asked my doctor and he said that everyone's body responds differently. Despite the medications side effects, my testicles generate semen and yet I look feminine."

My hand cupped her awesome plump bollocks, but I was very tired and drifted into a serene twilight.

"My love, do you miss having sex with a woman?"

Well, that woke me up! I was quiet for a few minutes.

"You don't have to answer if you don't want..."

"No, I will...you kind of caught me off guard."

I knew that Olivia was far from judgmental and would appreciate my honesty.

"If you mean, a woman with a vagina, yes sometimes. But when we have anal intercourse, I don't miss it, not one bit."

That made Olivia chuckle.

"So, you think of me as a woman, only a woman with a penis?"

"Yes, I don't ever think of you as a man or masculine in any way. In fact, your one of the most beautiful women I've ever seen, outside and inside. I thought when I first met you that you were out of my league.

Sometimes I miss going down on a woman, the heat of her sex, her juices. It's so different but at the same time similar. My ex, Shannon, could ejaculate occasionally, given the right stimulation."

Olivia tightened her embrace.

"Because I love you, sex takes on an entirely new meaning. I have a deep desire to please you, make you happy and that in turn makes me happy. I don't feel the need for 'tit for tat'. If I go down on you, I don't expect you to reciprocate."

"You liked the taste of my sperm from the very beginning. I'm curious, did you ever before me..."

"No, you were my first. I told you. I love the act of sucking on it, how it feels in my mouth, the hot, very hard flesh between my lips. I love how just before you cum, your penis swells even harder, then a twitch and a strong squirt of sperm which I usually swallow right away because your sweet cock keeps spurting, filling my mouth. The rich, earthy flavor and creamy texture is a big turn on for me. A slow gulp and I feel it flowing down my throat to my belly. Yummy!"

"You make me feel like the luckiest girl on the face of the Earth."

"Now you sound like Gary Cooper in "Pride of the Yankees"

"Yeah, I borrowed it but it's truly how I feel. I've always preferred getting head than giving. Don't get me wrong, I enjoy sucking cock, especially if I love the person."

Olivia nudged me in the side.

"Are you ready for me to..."

Olivia was gazing hungrily at my stiff pole.

"Go for it! I have a mild case of blue balls, they're in need of some relief."

Olivia deepthroated my penis until I practically yelled uncle. The sensation of the head and part of the shaft in her throat was beyond belief. The girl knew how to give head like a porn star. My balls tightened and an explosion was imminent.

"Oh yes...yes...I'm cumming!"

My cock erupted and squirt after squirt flew out. Olivia took it all then tilted her head back a little and opened her mouth, showing me the creamy load. A quick gulp and it was gone. She licked her lips with a very satisfied look.

"Umm...you have tasty sperm, my love."

Olivia gently cupped my balls.

"You say I have some big nuts, but these aren't exactly small."

"Yeah, but your penis is bigger and thicker than mine." I said with an injured look.

"Are you jealous?"

"Yeah, I am. It's also nicer looking, just beautiful. I wish I was circumcised."

Olivia pulled me tight to her body, kissed my forehead and cheeks tenderly.

"My dear sweet man, I love you beyond mere words. You can always get circumcised, but I understand it can be very painful for an adult male."

"The foreskin doesn't turn you off?"

"Of course not! I like pulling it back, the head with part of the shaft is so soft and silky smooth."

We stretched out on the bed, kissing and cuddling.

"Olivia, you never use the term 'blow job." Why?"

"That always bothered me, for example, you're not blowing on my penis, you're sucking it."

My hand was between her legs, fondling her limp cock.

"I'm not turning you on?" I asked with another injured look.

Olivia gave me one of her patented 'now really' looks.

"My love, give it a little time, my last orgasm was a dilly!"

Then I brought up a subject that I'd been thinking about a lot.

"Would you like to...sometime...maybe put your penis inside...me?"

Olivia's face lit up like a Christmas tree.

"Really? You're willing to try?"

"Yeah, I'd like to...but you're big and I'm...will it hurt?"

"Maybe at first...we'll use lots and lots of lube and if it does...we stop. I'll take it very slow, one step at a time."

I must have looked interested or eager.

"Oh Jason, I'm shivering with excitement. Just the thought of fucking your virgin behind is making me hard."

While I had a very muscular body from the waist up with a sharp V of my torso, from there down, I was slim with what Shannon always called a cute bubble butt.

"I'm willing to try. Is tomorrow afternoon good for you." I said in my best business sounding voice.

I'll put it on my calendar." She said with smirk.

Sunday was a typical day. We slept late, had a big breakfast, then off to the gym. When I returned home, I surprised Olivia with Primo hoagies. She loved the veggie, and I was a stickler for the Italian with hot peppers. There was a cool old sci fi film on TCM and we decided to watch "Forbidden Planet" After the movie ended, Olivia was looking at me with anticipation. Despite my willingness to give her my anal virginity, I was nervous, and she picked up on it.

"We don't have to rush into it, my love. When the time is right, we'll try, ok?"

I nodded but I had a case of the jitters. My beautiful and very smart girl, cuddled, kissed and for the first time stroked my nipples until I was panting.

"Feel good, my love?"

She knew perfectly well that it did. Her head moved lower, and her silky tongue licked and teased them until they were stiff.

"Can I suck them?" she asked in a coquettish voice.

"Yes, uh huh, yes."

Her mouth settled over my left nipple and suckled skillfully.

"Oh god, it feels amazing..."

By the time Olivia eased up my nipples throbbed like crazy, my cock was granite hard, and I was practically begging for her penis.

"Oh god, please take it! Take my butt!" I yelped.

When I looked, Olivia's cock was fully erect. She positioned me so that I was in all fours, my forearms clutching a bolster, butt raised and in the air. I could feel the cool air on my anal ring.

"I'm going to penetrate you from behind, that way it will be easier for you and for me."

"Do you have to use that word, penetrate?"

"I'm sorry, my love. Try to relax. I never want to hurt you in any way, so if we must stop, just say so. I'm curious, have you ever had a digital prostate exam?"

"Yes, I was having a problem urinating and the urologist wanted to see if it was enlarged. Thankfully it wasn't. While, it wasn't the most unpleasant medical experience I've ever had, it was close."

"I'm going to apply the lube, ok?"

"Ok."

The cold lube made me jumpy, but Olivia's fingers slid up and down my crack, applying pressure on my tight cluster. At first it felt weird but then weirdly good.

"Umm..." I moaned.

"Does it feel good?"

"Yeah, it does..."

Every time her finger probed my anal ring, Olivia applied more gentle force until her finger up to mid knuckle was inside me. There was some discomfort but as her digit wiggled in and out, my brain registered a very pleasant sensation.

"Umm...umm..."

Olivia removed her finger and I felt disappointed until I noticed her penis sliding up and down my crack. As she kept going, the head gently poked my rectum.

"Umm...umm...feels good."

The pleasurable sensation was building until my tight cluster relaxed and Olivia's penis penetrated.

"Oh!"

The intrusion caused a little pain, and she stopped moving inside me. She gently pushed and was a bit deeper, another little push and deeper still. It wasn't painful but it did hurt some.

"Ugh...oh...ugh..."

"Do you want me to stop?"

"No."

"Does it hurt?"

"Yeah, some but not enough to stop."

Holding my hips, Olivia made gentle in and out movements, moving deeper into my butt, the pain was worse but slowly it was replaced by a very pleasurable sensation. I could feel her cock on the walls of my bowel, and it felt better and better.

"Umm...umm...nice...umm."

"My love, is it better?"

"Yes, feels much better...umm."

Olivia leisurely fucked me, sliding in and out at a very relaxed pace. My cock was granite hard and seemed to pulse with every stroke.

"Oh yes...oh...feels soo good. Fuck me, beautiful fuck me."

I couldn't believe the words that left my mouth, but I was serious. Olivia's thick cock drilled my behind, going a bit faster and every time she went deeper, the pain came back but it lasted only a few seconds replaced by this intense pleasure.

"Ugh...ugh...ugh...ugh." I moaned lustily.

"Are you ok, my love?"

"Oh god, yes! It feels great. Fuck me...oh...fuck me!"

Olivia was wise enough to keep an unhurried pace, but she was going deeper as

my bowel gripped her penis.

"Oh, my love...I'm all the way inside you." she groaned.

Indeed, she was as I felt her balls bobble against me. My first rodeo and I took her entire length. It made me feel proud.

"I'm going to cum, my love..."

"Cum inside me...I want your load inside me!" I yelled.

Olivia's was executing long strokes, almost pulling all the way out then plunging deep. Her upper body was draped on my back when I felt her tense up.

"Oh yes! Oh yes! Oh yes!" she howled like a she wolf.

Immediately, I sensed a gush of warm fluid in my bowels.

"Oh yeah! Pump your load inside me! I want it all!" I shrieked.

One last thrust and Olivia reached under me grasping my steel hard pole, a couple of jerks and I unleashed a torrent of sperm on a towel she had placed under me. I literally collapsed forward, unable to move.

"Jason! Are you ok?" she spoke in a panicked voice.

"Yeah..." I managed to croak out.

Olivia was on top of me holding my body, stroking my hair in her tender way.

"Oh god, if I hurt you...I'll never forgive myself."

She turned me. I lay limp in her embrace as she sweetly kissed my sweaty face.

"Oh, my poor baby, what have I done!"

She called me baby, and it warmed my heart. I looked up at her smiling.

"You called me baby..." I spoke in scratchy voice.

"My dear sweet man, I love you so much."

With all the goop and bodily fluids on me I felt yucky. Olivia must have read my

mind.

"Come on, let me help you to the shower."

I was still weak, but my strength was coming back. Olivia positioned me on the triangle seat in the corner as warm spray washed over me. With a washcloth in one hand and soap in other, she lovingly cleaned my body.

"Can you stand up?"

"Yeah..."