It Started with Football

Note to All - No one under the age of 18 is engaged in any sort sexual activity in this fictional story. It is neither implied, inferred, suggested, or endorsed by this author.

It Started with Football, Part 1

Rob - (me) - 26 years old - 6'3", 210 lbs. medium brown hair, blue eyes. Caucasian.

Terri - (sister to Rob), 27 years old - 5'10" 135 lbs., medium brown hair, blue eyes. Caucasian.

Emily - (an interest of Rob) 24 years old - 5'5" 115 lbs., 36B-24-34, dirty blonde hair, brown eyes. Transgender.

My name is Rob and I love football. I love college football and professional football. When tickets for the new NFL season went on sale, I decided to buy season tickets and I found a good seat where I had a good view of the field and I wasn't in the sun at all during any of the home games. My seat was an aisle seat and was also in a good locale due to its proximity to the nearest restroom and concession stands. The new season couldn't get here fast enough so that I could go and root for my favorite team during the upcoming season.

The first Sunday of the new season rolled around and my team was playing its first two games of the season at home. I got to the stadium, found a spot in the parking garage, and made my way inside the stadium. I had eaten before I left home but I did decide I wanted to order a beer and take it to my seat. I paid for my beer and went to where my seat was at. I sat down and watched the two teams warm up and the pregame festivities on the field. I was dressed for the weather as well. Even though it was September, it was still hot so I had chosen some gray shorts, a black shirt with my favorite team's logo on it, and a pair of sneakers. I settled in to enjoy my beer. About 30 minutes before kickoff, a pretty young lady with dirty blonde hair and brown eyes walked toward where I was sitting and said "Excuse me" so I moved my legs aside and she sat in the seat next to me. She was wearing a short jean skirt, a black t-shirt, and some black Chuck Taylors. And she smelled AMAZING!!!!!! Her perfume was soft and permeated pleasantly into my nostrils. She initiated the conversation -

"Hi. I'm Emily."

"Rob" It's nice to meet you.

"It's nice to meet you as well."

"This your first time here?"

"No. I came to some of the games last year and had a good time. So I decided to buy a season ticket this year."

"I decided to buy a season ticket for this season as well so it looks we will be seeing each other at all the home games."

"Cool. I'm ready for some football."

"Big sports fan?"

"Yeah. I love all kinds of sports."

"Me too."

We sat and enjoyed the game and made small talk throughout. There was just something so charming and pleasing about her. At the end of the game, which our team won, we were making our way out and she said she was parked in the parking garage on level 8. I told her I was on level 9. We continued talking as we walked and I told her, based on the size of the crowd, it would be a while before we would be able to leave the parking garage.

"What are you thinking?" She asked.

"Well, there is a donut shop that makes fresh homemade donuts about three blocks west of here. I stop off there every morning on my way to my business."

"You have your own business?"

"Yeah. I own a construction company and we build homes and businesses. We also do renovations as well. Been doing that for four years now. What about you?"

"I am a paralegal for a law firm downtown, about three blocks from the donut shop we're heading to. Been there two years and I love my job."

We got to the donut shop. I ordered an apple fritter and a medium coffee with extra cream and sugar. She ordered a donut with lemon glaze and a small coffee. We took a seat in one of the booths, enjoyed our snacks, and chatted for about two hours. The traffic outside was dwindling down so we walked to the parking garage and took the elevator to level 8, where she was parked. We said our goodbyes and I told her I would see her next Sunday. I went to level 9, got in my car, and went home.

The next Sunday, we took in the next home game and chatted more. I was really enjoying getting to know her. This time though, we were both parked on level 9, as we discovered during one of our conversations. She was dressed in some cute jean shorts instead of a skirt. After the game, we decided to go back to the same donut shop and, after a two hour stay, we left to go to the parking garage.

When we got to level 9, thanks to the elevator, I walked her to her car and said "Well our team is on the road for next two games. Did you want to get together and watch the game somewhere or do you have plans?"

"I don't have any plans. There is a sports bar about a half mile from my condo. I could meet you there? Yes? No? Maybe?"

"I would like that. I enjoy your company and have enjoyed getting to know you. You are really nice and easy to talk to."

"Well thank you Rob. BUT there is something I want to tell you about me before this goes any further or any emotions come into play."

"Ok Emily. What's up?"

She took a deep breath and said "Rob, I uh..........I............."

"Emily please tell me???? Pretty please????"

She took another breath. "Rob I was born as a male. I've been on HRT since I was 16. And my penis ain't going nowhere. I don't wish to have it removed because I have heard too many horror stories about those and from those who decided to have SRS."

I paused for a moment. "Emily, I am glad you were honest with me. Thank you for that. This newly divulged information doesn't change our friendship and doesn't change the fact I want to spend time with you. And, before you ask, yes! I will still meet you at the sports bar next Sunday. I know kickoff isn't until 4:25 PM so want to meet outside at 3 so we can find a good table?"

"Yes. That would be awesome. I'm looking forward to it."

"So am I." I leaned in and kissed her on the cheek.

She smiled and I opened her car door and closed it after she got in. She waved and she drove away. I got in my car and called my sister who lived about 25 minutes from the stadium.

"Hello?"

"Terri, it's Rob. You gonna be home for the next hour or so?"

"Yeah. What's going on?"

"I've met someone and I need your help."

"Ohhhhhhhhh ooooookkkkkaaaaayyyyyyyyy."

"See you when I get there."

"Ok bye."

"Bye."

I got to Terri's house and knocked on the door. She told me to come on in. I sat on her sofa to let her know about Emily.

"Ok Rob. What's going on? I could hear the urgency in your voice."

"Yeah. Soooooooooo I met this lady at the first two home football games. Her name is Emily. She's pretty. Not pretty. She's gorgeous. She's smart. She's funny. And I really like her."

"Ok. How do I fit into all of this?"

"Well, see Terri, she.................uh...............Emily is a...............Emily has a............"

"Damnit Rob, out with it!!!!!!!"

"Terri, my new friend Emily has a penis."

"Ah, I see."

"Terri, I have never had a penis in my mouth and I've never had one in my ass either. If things progress to that point, I don't want to give a lackluster performance. Ya know?"

"So you want me to teach you?"

"Could you please? I know it sounds completely off the wall and nuts, pardon the pun, but I like her and I want to be able to please her if things ever get to that point."

"Well Rob, you are my brother and I do love you so yes.............yes I will help you."

I grabbed her by her face cheeks and kissed her about a dozen times all over face "Thank you thank you, thank you,, thank you, thank you, thank you. You're the greatest sister in the world. Did I mention you're the greatest sister in the world?"

She started laughing. She stood up and grabbed me by the hand. "Come on you big lug." And she led me down the hall to her bedroom.

Terri looked at me "Don't think this is weird but I'm gonna need you to strip."

"Huh? Do what?"

"Trust me. You'll see why in a few minutes."

So I stripped and then Terri stripped. Here we were, both nude. We hadn't seen each other nude since the infamous "Skinny Dip Dare" in Destin, Florida two years ago. She reached into her middle dresser drawer an pulled out an assortment of sex toys and laid them on the bed.

I looked at her with a big grin on my face.

She quipped. "Hey a girl's gotta do what a girl's gotta do when she doesn't have a man to please her."

I giggled. "Point taken."

"So how big do you think Emily is?"

"I forgot to ask her before I called you earlier." We both burst into laughter.

"Here, let's go with this one." Terri picked up a pink, realistic feeling dildo that was about 7 inches long. She took it and placed it into a strapon harness and laid back on the bed.

"OK now I'm laying back and you're gonna suck my "cock". You want to use lots of saliva and pretend your mouth is a pussy as you go up and down on it. And key point, use LOTS of tongue. Rumor has it that you guys like that quite a bit. And hold the cock by the base so that it doesn't go all over the place. So, show me what ya got."

I placed my mouth on the phallus with my eyes closed and started moving my head up and down.

"Don't close your eyes. Maintain eye contact with the person you're sucking. And rub their legs, and tummy and breasts, since Emily has breasts, softly. It's very sexy and lets the person know you're into them."

I opened my eyes and made eye contact with Terri. She had such a lustful look in her eyes. Up and down I bobbed my head, using lots of saliva and tongue as instructed. Some of my saliva dripped onto her pussy and she moved her hips back and forth. I kissed and licked up one side of the dildo and down the other side, never breaking eye contact with Terri. My cock was stirring under me and I could feel precum oozing out of my cock onto the bedspread.

"Goddamn Rob!!!!! This is so fucking hot. You sure you've never done this before? You look amazing sucking this dildo. I know what I'm gonna be doing when you leave tonight."

"Thank you babe."

"I love when you call me babe. Makes me feel special."

"You ARE special. You're my sister, my best friend, and my greatest ally and I love you more than you will ever realize."

I went back to sucking on the dildo and looking at Terri. I could smell the heat coming from her pussy. She smelled so good down there. I paused to look at her pussy.

"What?" She asked.

"Oh, just looking at your pussy. I love your little landing strip. Your lips appear to be quite wet."

"Well, it's about 50-50 on your saliva and my lubrication from watching you suck on the dildo. Are you ready for your anal experience?"

"OK, but please be gentle."

"I will. I promise." And then she leaned forward and kissed me softly on the lips.

She moved around on the bed and told me to get on my knees and to spread my legs wide in the doggy position and rest my head on the pillow she gave me. I'm not a hairy person so I am virtually hair free in my genital and anal regions. She ran to the bathroom and came back with her electric razor, some lotion, a wash cloth, and some lube. She gave my balls and asshole a quick shave and wiped off the area with a warm wash cloth. She put just a little bit of lotion in the newly shaved areas, let the lotion set for a few minutes, and then she wiped everything down there with the warm wash cloth. Being so open, spread, and vulnerable had my cock drooling all over the bedspread.

"Oh, looks like someone is really enjoying this treatment." She said.

"It started when I was looking into your eyes sucking your dildo."

"You liked that?"

"Yeah you looked so sexy when I was looking into your eyes."

"You looked hot as fuck with that dildo in your mouth."

She took some of the precum that was coming out of my cock and smeared it on my asshole. She then took some lube, placed it on two fingers, and inserted them into my ass to get it ready for the strapon. I don't know what made me do it but I started rocking back on her fingers.

"WOW Rob. You're into this, aren't you?"

"I don't know why but it just feels so good."

"Ready for me to make love to your asshole?"

"Yes I am."

She put some lube on the dildo and slowly eased into me. I was amazed at how well it fit and how great it felt.

"How does it feel Rob?"

"I feel so nice."

She moved into my ass, slowly at first and then she increased the speed just a little. I was feeling so damn good. My cock was drooling all over the bedspread.

"Want me to go faster?"

"Yes babe please."

She started fucking my ass faster. I was like a bitch in heat. This might have been my first anal fuck but I was certainly hoping it wouldn't be my last.

"Terri, fuck me hard babe. I love you. I love your cock. Pound my ass please love."

"Oh Rob I love you too............so much..................so fucking much. I want to fuck you everyday."

My cock twitched and throbbed when she said that. She reached around and grabbed my cock. I froze. She stopped.

"What? Is everything ok? Are you ok? Is something wrong?"

"Terri, I don't know how to explain it. I can't explain it. When you touched my cock..........you've never touched my cock until now."

"I wanted to. I'm sorry. I am so so so so sorry."

I pulled the dildo out of my ass and turned to face her. I pulled her to me and said to her "Terri, you're the one constant in my life and we have been through hell and high water together. I have never had anyone love me like you and I've never loved anyone as much as I love you."

"Kiss me Rob."

And kiss her I did. For the next several minutes, nothing in the outside world mattered. The only thing I cared about was showing my sister how much I loved her through the passion of my kisses. My cock pressed into her stomach. She broke our kiss for a moment.

"Make love to me Rob."

I eased her on to her back. I slid easily into her pussy because she was so wet. I made love to Terri for the first time in my life. I had never wanted anyone more than her. I had never wanted her until today. I had no sexual inclinations toward her until today. Had I been hiding my true feelings? Had she been hiding her true feelings? As we made love, we smiled and looked deeply into each other's eyes. Our looks, our smiles, our bodies, our emotions, our heavy breathing - they did all the talking so that our mouths didn't have to speak. For the next 45 minutes, we made love like new lovers, like passionate lovers - I didn't want it to ever end. We changed positions so that she was on top, we were on our sides, we did doggy, cowgirl, reverse cowgirl, pile driver, on the bed, in the bathroom, on the dining room table, on the kitchen counter, on the sofa, on the loveseat, on the guest bed in the guest bedroom, on the back patio, and we ended back in her bed. The sexual aerobics with Terri was so passionate, romantic, lusty, fulfilling - damn I loved her so fucking much. I'm not sure how many times I made her cum because she was very in tune with our lovemaking. There were several times when she told me she was cumming and other times she was so overcome with passion that she tried to kiss the lips off of my face. We exchanged "I love you's" more times than I can count.

She looked at me and said "Rob, when you cum, I want you to stop pumping because I want us to be perfectly still when you cum in me. I want to feel your cock pulsing inside of me.

I kept up a good pace for a few more minutes, then I looked into her eyes, and said "It's time for me to cum."

I stopped moving. She stopped moving. We felt my cock pulsing as I emptied my seed into her. We never broke eye contact. We smiled at each other. After my cock stopped pulsing, our faces came together and we kissed so softly, so passionately, so lovingly.

And when I pulled back, she looked at me and put my face in her hands and said "I love you Rob, so very much, and more than ever right now."

"I love you too Terri with all my heart."

"But I do have a question?"

"Yeah?"

"What are you going to do about Emily?"

"Oh crap. I haven't even given that any thought. I'll have to think of something."

"Well I hope so. Because I'm not sharing you with anyone. I love you far too much for that."

"And I love you Terri. I want you and me and US!"

I moved off the top of her and laid on my back. She laid on her side, partially on my chest. I reached for her hand to hold, kissed her on the lips, and we fell asleep.

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Part 2 is coming. Rob comes clean to Emily but doesn't tell her the depth of the relationship with Terri.

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Thanks for reading everyone. Please rate my story and comment. Have a great day everyone!