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All-American strap-on Ch. 3

A lesbian and a straight guy try make their relationship work

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October in Boston is usually a fun and festive time of year, especially when the Red Sox are in the MLB playoffs. This year, the city was buzzing as the Red Sox prepared to play the Toronto Blue Jays in the first round. Fortunately, Allison, like me, was also a big Red Sox fan and the two of us were excited to follow the upcoming playoff games together.

By this point, Allison and I had been on a couple of dates together and had been pretty intimate with each other, however I was unsure where our relationship was headed. She had made it clear to me that she wasn’t attracted to guys, yet she seemed more than willing to fool around. I needed to know where things stood.

One day after class, I suggested we grab a cup of coffee and talk. This time, instead of sitting at the coffee shop we decided to walk around the main campus quad as we sipped our drinks. Allison must have been thinking about the same things I was thinking because she beat me to the punch.

“I’ve been thinking,” she said.

“Me too,” I replied.

“I’ve never been in a relationship like this with a guy before,” she continued.

We both sipped our drinks as we continued to walk. I could tell she was thinking about what she wanted to say but having trouble getting the exact words out.

“I guess what I’m saying, is that I like you and I like spending time with you, but I don’t’ know where this will go,” she said as she turned towards me.

We both stopped walking and faced each other.

“I imagine this must be confusing for you,” I replied.

“It is,” she said.

“What if we don’t set any expectations and just take things day by day?” I suggested.

Allison thought for a moment and smiled at me.

“I guess we can,” she said.

I smiled back at her.

“But just to be clear, I don’t want to have sex with you. At least not conventional sex,” she said.

I nodded and smiled.

“I understand,” I replied.

We then turned and slowly resumed walking as we both sipped our drinks. I quickly changed the subject to break the awkward silence.

“So, do you think the Sox have a chance against the Blue Jays?” I asked.

“I think they do,” Allison replied.

“Me too,” I said as I took another sip of my coffee.

“It’s sad to think that this is our last semester at college and our last Red Sox playoff season as students,” she said.

It suddenly struck me that she was right. It would soon be the end of an era for both of us.

“Oh my god. I didn’t even realize that,” I said.

“Uh huh,” Allison said.

“That’s so sad,” I said.

“My roommate and I are having a few people over at our place to watch the game. Want to join us?” she said.

“Sure,” I replied.

“Great, you can come by around 7,” she said.

“I’ll bring some Octoberfest,” I said referring to the Sam Adams brewery popular seasonal beer.

“Perfect!” she said.

I then looked at my watch.

“Alright, I gotta Eryaman Escort go meet one of my professors. I’ll see you tonight though,” I said as I began to walk away.

“See you later,” she replied as we both parted ways.

As I walked away, I smiled to myself. At least Allison was open to keeping things going between us; wherever it might lead.

The next few hours flew by and before long it was time to head to Allison’s apartment.

After picking up a twelve pack of Sam Adams Octoberfest, I excitedly headed over to Allison’s apartment. After being let inside, Allison greeted me a hug and kiss. She was wearing a faded Boston Red Sox hat and wore her hair in a pony tail. She looked sexy. Allison then introduced me to her roommate, a cute blonde named Alexis and a couple of her girlfriends. Conveniently, I was the only guy in the group.

I then proudly put the twelve pack of beer on the table and opened it, passing bottles around.

“Octoberfest is the best!” one of the girls remarked.

“I agree,” I said with a smile.

We then all settled down in the small living room and gathered around the television. I ended up sitting on the end of a futon couch next to Allison. It was definitely a tight fit as four of us squeezed onto the futon, but we made it work. One of the girls was fortunate to claim the lounge chair. As I sat there, I debated putting my arm around Allison. Part of me wanted to go for it, but the other part of me wondered if Allison wanted the other girls to know about our relationship; if you could call it that.

Suddenly everyone stood up as the national anthem was played before the first pitch. When it was over, we all sat down again. This time, much to my surprise, Allison put her arm over my shoulder. I looked over at her and we both smiled at each other. This was a first for me, but there had been many firsts for me with Allison.

For the next two hours, we enjoyed watching the game together with her roommate and her friends. Each time, the Red Sox scored, we all got into it, cheered, stood up and high fived each other. Allison’s roommate Alexis had quite the sense of humor and frequently offered her own play by play during the game. It was very entertaining. Fortunately, the Red Sox prevailed and won the game.

After it was over, we all sat around discussing some of the highlights of the game, before Alexis suggested we all go to a nearby bar to have a drink and celebrate with other students. Allison looked at me with an expression as if to say I don’t want to go out to the bar. I nodded in agreement. We stayed put on the couch as Alexis and the other two girls got their coats and prepared to head out to the bar.

“See you later,” they said collectively as they walked out.

Once they had left the apartment, I turned to Allison. As we both sat there looking at each other, I leaned in and kissed her on the lips. She met me half way and we kissed passionately for a few seconds before pulling away from each other.

“I’ve been wanting to do that all night,” I said.

Allison grinned. She Sincan Escort then stood up and slowly walked out of the room. I got up and followed her into her room. Once we were both inside, she closed the door. She then took off her Red Sox hat, untied her pony tail and let her hair down.

“Tonight, I want to blow your mind,” she said with her trademark mischievous grin.

I instinctively looked over at her dresser insinuating she was going to use her strap-on again.

“I have something else in mind,” she said.

I nodded.

“Why don’t you get undressed and get on the bed,” she suggested.

We then both slowly began to undress. Once I was naked, I walked over and lay on her bed. Allison then walked over to the dresser and took a bottle of lube out of the top drawer, before walking over and laying next to me on the bed.

“You’re so hot,” I said as I took in her toned body and perfect tan complexion. I then reached over and gently began to caress her breast. By now, my penis was fully erect.

Seeing my excitement, Allison slowly put her hand on my erect penis.

“I’m sorry, my hands are cold,” she giggled.

She then began to touch the head of my penis using her thumb and pointer finger; soon finding my sensitive spot. It was one of the many moments in my life that I was thankful I had been circumcised.

“I need you to tell me what feels good,” she whispered as she leaned in and kissed my neck.

Shen then opened the bottle of lube and applied some to her hand. We made eye contact as she slowly reached down with her lubed hand and began to gently caress my penis. I then took my hand. Placed it over hers and guided it in a stroking motion. Soon her hand was fully cupped around my penis as she moved it up and down my hard shaft and I moved my hand away.

At first, her motions seemed robotic but after a short while she became more relaxed and her touch seemed more natural.

“A little faster,” I whispered.

She then picked up the pace and began to take longer strokes.

“Does that feel good?” she whispered.

I nodded as she continued to stroke me. I desperately wanted to fuck her then and there, but I knew I would have to settle for a hand job. As I looked at her face, I could tell she was captivated by what she was doing. I imagined this was the first time she had ever seen a penis up close, let alone given a guy a hand job.

Gradually, I built towards an eruption and my breathing picked up and my legs began to spasm. As I came, I reached out and stopped her hand from moving. She then watched in awe as large spurts of white cum shot out of my penis and landed on my stomach.

Soon after word, Allison slowly removed her hand, which was sticky with lube. She then smiled at me.

As I lay there in a state of bliss, Allison got off the bed. She then slowly opened the door to her room and peaked outside. Sensing the coast was clear, she quickly tiptoed towards the bathroom. I soon heard the water running and assumed she was washing her hand. A minute later, she returned to the room and Etlik Escort shut the door. She then got back on the bed and laid next to me.

“How was that?” she asked as she handed me a couple of tissues to wipe myself off.

“Amazing!” I said as I wiped off my stomach.

“Good,” she replied.

After I was done wiping myself off, I crumpled up the tissues and threw them in a small garbage pale next to her bed.

“Can I repay the favor?” I said, as I slowly rolled over on my side to face her. I then reached my hand down and gently touched the stubble of hair above her pussy. I slowly parted her pussy lips with my middle finger and could immediately feel her wetness. After a few seconds, she gently pushed my hand away and sat up.

“I want to fuck you,” she said as she stood up and went over to her dresser.

She then took out her purple double-sided strap-on and put the harness on her waste and adjusted it on her hips. Once that was done, she put a condom on the strap-on and applied some lube. Having watched this routine a couple of times before, I was always amazed at how methodical she was about putting the condom on the end of the dildo.

Once she was ready, she came back to the bed.

“Lay on your stomach,” she whispered.

I did as she instructed and sprawled out on my stomach with my arms laying crossed under my chin. Once I was in position, she got on top of me and straddled me.

I felt the end of the strap-on brush up against the back of my leg as she slowly got into position. Once she was settled, I began to feel the head of the dildo against my butthole. Instinctively, I flinched.

“Just relax,” she whispered as she continued to guide the head of the strap-on into my butt. I winced a little as she pushed it in further.

Then, without any warning, she suddenly thrust into me; burying the strap-on deep inside of me.

I let out a yelp.

“Ooooh,” I moaned as Allison settled on top of me.

“Breathe,” she whispered as she kissed the back of my neck. Somehow, she knew that always had a strange calming effect on me. I also felt her hard nipples pressing into my back.

“Why did you do that?” I groaned.

“Sometimes you just have to rip off the Band-Aid,” she said.

“It hurts,” I said.

“I know it does, but try to relax,” she replied.

She stayed still for a short while, letting me adjust to the strap-on inside of me. She then propped herself up on her hands and began thrusting in and out of me.

“That’s it,” she whispered as she began to pick up the pace of her thrusts.

As I lay there trying to ignore the discomfort I was feeling, I heard the outer door to Allison’s apartment open. It was immediately followed by the sound of multiple voices and footsteps. I gulped. Allison’s roommate and the other two girls must have returned from the bar. My heart sank as I suddenly realized Allison hadn’t locked the door to her room.

“Allison, your door…,” I whispered.

“Shhh,” she replied.

“Your door isn’t locked,” I said; this time a little louder.

“It’s ok, just try to relax,” she said as she began to moan and continued thrusting in and out of me.

All of a sudden, I heard footsteps approach the other side of Allison’s door. I turned my head towards the door, just in time to see the door knob slowly turning.

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Till next time…..stay tuned for more.

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