My First Anal Part 3

Jason and I had an amazing weekend of our first sex together and I wanted to make the next time even better.

The entire week at school Jason and I would send messages to each other. Some were dick pics. Some were things we wanted to try. Some were things we already did and we were reliving them.

We made an agreement that we wouldn’t have sex every time we got together. We had spent the better part of 2 years now completely comfortable sucking each other’s cocks 2 or 3, sometimes 4 or more times a day. So we thought we’d keep doing that and save sex for weekends and sleepovers. That gave us something to do now and something to look forward to later.

All week we brainstormed on ideas, like positions we wanted to try, or even places we wanted to have sex. Jason liked the idea of us having sex in public places. I was a bit nervous about that.

One thing I hadn’t shared with anyone, including Jason, was that I regularly dressed in women’s clothes when I masturbated. I had been secretly stealing and wearing my moms underwear, lingerie and even her day to day clothes since I was 10. I had assumed I would take that to the grave with me at the time but since Jason and I actually had sex the prior weekend, that was something I had considered revealing to him.

As the week got closer and closer to ending I became more and more anxious about telling Jason about my idea. Part of me wanted to tell him and part of me was scared he’d freak out. I don’t know why I thought that, he was ok with having sex with me, but I was still terrified.

Friday night we made plans together and I had decided not to tell him just yet. We spent the night at his house, as we usually did, we rarely stayed at mine. We eagerly waited for his parents to go to bed and when the did, we raced downstairs and had very similar sex to the prior weekend. About an hour later, we had sex a second time, and then a third in the middle of the night when we both were had woken up.

The following day we were exhausted if I can be honest. I felt very weak in the knees and a bit drained. I knew we were going to spend Saturday night together but I wasn’t sure I was going to be up for another night like the previous.

During the course of our Saturday, I received a message from my mom saying she was going to a company Christmas party and wouldn’t be home until late. I immediately changed my entire mindset about how I felt. I excitedly told Jason that we could have the house to ourselves if we stayed at my place tonight and he jumped at that opportunity. As the evening progressed I made the decision that I was going to let Jason know about my secret. If I was going to do it though, I was going to go all in. I didn’t want to leave anything on the table. This was going to be me showing him me.

After my mom left we immediately began kissing on the couch and making out pretty intensely. Jason suggested we go take another shower together but I swallowed the lump in my throat and suggested something different.

Jason was excited about the idea of something different but I didn’t tell him what yet. I had him go in my room and get into bed and wait for me.

I nervously went into my mom’s bedroom and began shuffling through her drawers. I knew exactly what I was looking for but I didn’t know where it was. My mom and I have similar bodies. We’re both overweight and her clothes have always fit me perfectly.

I finally found what I was looking for and I raced to the bathroom to get ready.

The first thing I put on was a black silk thong and a see through black babydoll that had holes where the nipples are. The first time I ever put this outfit on, I stood and looked at myself in the mirror and thought how lucky my dad was to have a mom, who despite being overweight was a sexually charged woman and wore sexy lingerie for him.

This time I stared at myself and hoped Jason felt as lucky as I hoped my dad was.

I slid a pair of black stocking I had bought myself on to go with the lingerie. Halloween was just a couple months prior and I had spent the bulk of what money I had on sexy clothes, wigs and makeup. I quickly applied some red lipstick and I did a horrible job on my eye makeup. I through on a long brown wig that was almost identical to my hair color and I stared at myself in the mirror once more. I had dressed myself like this and others like it thousands of times and never felt so nervous about it. I took a deep breath and left the bathroom.

“Are you ready?” I asked as I knocked on my bedroom door

“Yeah!” Jason responded excitedly

One more deep breath and I opened the door. Jason laid sprawled out on my bed completely naked with his rock hard cock in his hand. His jaw dropped and he sprung up to his feet when he saw me.

“Holy shit! You look amazing!” He said before he kissed me. “How did you come up with this idea?”

“I’ve been doing this for years. These are my mom’s clothes.” I explained

“Wow, your dad is a lucky man.” He said

That made me laugh and completely forget about how nervous I was.

Jason took me in his arms and put his tongue in my mouth. Our tongues swirled around each other in unison. His strong hands began to caress my body, squeezing my ass a few times and running his hands up my back. I could feel how hard his dick was as it pressed against my stomach.

“I like these little holes.” Jason said referring to the nipple holes in the babydoll

He proceeded to bend down and swirl his tongue around my erect nipple. I was so turned on! If I had a pussy it would’ve been drenched!

Jason lead me to the bed and laid me down on my back. Got on top of me and we resumed making out and groping each other. I couldn’t stop thinking about his cock pressed against me!

“I wanna suck your cock so bad right now!” I cried out

“Let’s 69!” He suggested

In all our time of sucking each other off we had only 69’d a couple times and it was always side by side. This time Jason hopped off me, laid on his back and told me to get on top. It somehow made me feel more like the woman I was dressed as.

We 69’d for just a minute or so before I couldn’t take it anymore. I stood up, removed the thong and babydoll and grabbed the bottle of lube, yes we got some lubricant this time.

“How do you wanna fuck me?” I asked

“Lay on your back again!” He answered quickly

I laid on my back and squirted some lube in my hand and stroked it all over his cock. I could feel it warming up and Jason even made a comment about it tingling a bit. I laid back and lifted my legs. Jason climbed next to me and pressed his dick against my eager hole. As it popped in I yelped and he gasped. He began slowly grinding in and out of me and softly running his tongue up my stockings. His hand reached down and began playing with my nipples and I thought I was going to lose it.

Then something changed. My legs fell off his shoulders and I wrapped them around his waist as best I could pulling him closer to me. He leaned down in more of a missionary position and our eyes locked for what seemed like an eternity. Then I saw him bite his bottom lip and arch back thrusting his cock deep inside me. I squeezed his flexed ass cheeks as he pumped me full of sperm. I felt every pulse as his cock spurted shot after shot deep inside my hole!

When we finished, we took a shower together so I could wash off the makeup. Jason gave me an incredible blowjob in the shower and thanked me for the amazing sex. After the shower we immediately got into bed and started fooling around again. We had sex 4 more times that night and exchanged blowjobs in the morning.

Ever since that night I have had two sides to me sexually. One is a male that loves fucking women and the other is a woman that loves being fucked by a manly man!

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