Things Take an Unexpected Turn

As our roles become more defined in the relationship things take a very unexpected turn.

J and I had just finished the 9th grade. Since he moved we went to different schools but still managed to hangout most weekends. At the beginning of the school year we had just taken a big step in our secret relationship when I introduced oral sex. Since that night, we’ve had a difficult time doing anything other than suck each other’s dicks when we’re together. Both of us enjoyed giving and receiving by the end of 9th grade.

Summer was here now and that meant we could hangout just about anytime we wanted and sleepover at each others house any night as well. J had just gotten his drivers license and now we were mobile as well!

Our plan for this particular night was to stay at his house. We found it a little more relaxing and a bit easier to carry on the way we did at his house over mine. I mean, his dad was gay and living with his boyfriend so we always knew if we were going to get caught, probably better if his dad catches us instead of my mom.

We started the night at the movies. The film ended around midnight and we headed over to J’s house. Upon pulling into the driveway we noticed lights were still on and there was a few cars parked outside. We didn’t have to go inside to know what was happening. Even if they weren’t having some big gay orgy, there was a bunch of people inside which would make it a bit difficult for us to do anything.

We decided to go to my place instead. By the time we got there it was pushing 1am so we had to be quiet. My mom had to work the next morning.

J and I sat on the couch and just started kissing and groping each other a bit. We had become so turned on by the heavy petting and spit swapping that we almost didn’t hear my mom coming down the hallway. We quickly pushed off each other and sat nervously out of breath as my mom walked by.

Not long after J and I started fooling around with each other, J started making jokes and comments about how he thought my mom was hot. I would always combat them with the stereotypical joke about black guys liking thick white women as a way to mask my discomfort with the subject.

“Oh, I didn’t know you boys were here, you scared me. Why are you sitting in the dark?” She said as she turned on the light.

As I mentioned my mom was a bigger woman. Not huge but thick. It’s certainly where my being overweight comes from. She was wearing what I assumed was her favorite negligée. It was a dark blue silk slip dress with black lace around the edges. I assume it’s her favorite because she wears it in particular times.

My dad left us when I was just 7 and my mom never dated or anything afterwards. Around the time I started getting into sex, I started noticing my mother as she was the only female I knew. Despite my dad leaving us, he would come over once or twice a month to have sex with my mom. This went on until I was in college. My perception skills are a bit higher than most and I noticed that whenever my mom wore that dark blue slip dress, my dad was also in the bedroom. I learned a shit ton about sex by listening to them and or secretly watching them have sex over the years. And yeah.. the reason I got uncomfortable when J joked about my mom was because I kind of wanted to know what it was like to have sex with her as well. Something that definitely did NOT happen.

“We just got here and we’re going to go to bed now.” I answered.

Mom came out of the kitchen with two beers which confirmed my suspicions.

“Dad’s here I take it?” I asked already knowing the answer

“Is that a problem?” She asked

“Don’t you have to work in a few hours?” I asked as she made her way down the hallway and closed the door without answering.

J and I made our way to my room and despite not being in a very good mood anymore, I reluctantly sucked him off and then we went to bed.

The next morning J and I woke up later than usual and my mom and dad were both gone. Once I saw the apartment was empty, my teenage libido kicked in and J and I ended up taking a shower together where we exchanged blowjobs.

Over the course of the summer J made more and more comments and hints that he’d like to see me dressed as a woman. I tried to play it off but secretly inside I was excited about the idea. The one thing J didn’t know about me at the time was that I was already dressings in my mom’s clothes when I would masturbate. It started with my curiosity about my mom and then turned into I loved how the clothes felt on my skin. Especially the silky lingerie and underwear. The more J mentioned it, the more our roles became more finely defined which I admit scared me a bit which is why I was not exactly eager to tell him my secret.

J’s dad’s boyfriend was unemployed and always around the house so my house became the place where we started messing around. With my mom gone at work and summer vacation in full swing, we had the house to ourselves for 8 hours everyday if we wanted.

I had been mentioned me in drag more and more and I knew it was no longer a joke but something he wanted sexually. It’s probably a good time to mention that at this point, we hadn’t said it, but we were undeniably in love with each other. It was noticeable when we kissed. It was noticeable when we laid in bed together, and it was noticeable when we talked together. There was no mistaking it. If I didn’t have feelings for him like that I probably wouldn’t have considered dressing up for him but I decided that I was going to do it. And yeah, once I did I fucking loved it!

We made plans to sleepover at my house that night. It was a weekday and I knew my mom would be early to bed and gone in the morning leaving us virtually alone. While my mom was at work I rummaged through her dresser drawers finding a few things J might like.

First I found a black silk babydoll. There was a matching pair of panties that went with it I grabbed and lastly I swiped a pair of black stockings. While showering I had an idea to shave my legs. When I finished, I found myself incredibly turned on. So I went a step further and shaved the area around my cock and balls. Feeling how smooth it had gotten turned me on more. Each step I took made me hornier and hornier. I even put on some makeup and lipstick to see if I could. It looked terrible in retrospect but I went with it anyways.

After I was done shaving and cleaning all the practice makeup off my face I went to my room and tried on the lingerie I took from mom. It felt so hot running my hands up my smooth legs in those stockings. It was another 3 hours before J was coming over and I couldn’t wait. I had to masturbate.

When J finally got there, we sat on the couch and watched a TV while we waited for my mom to go to bed. I nervously tapped my fingers and couldn’t sit still while we waited. I was so incredibly nervous!

Mom went to bed around 9pm and as soon as we heard her bedroom door shut, we grabbed ahold of each other and began making out and groping each other. I had to be careful how far the groping went though since I was already wearing the black silk panties. Didn’t want to spoil the surprise.

We kissed and talked for about an hour and when keeping it in our pants had seemed impossible going forward, we got up and headed to my bedroom.

I instructed J to get into bed while I went to the bathroom for a minute. I had a small bag stored under the couch and I quickly ran back and grabbed it. I threw my clothes off in record time and put on the black silk babydoll and black stockings. I knew I couldn’t do a whole makeup look because I had no idea what I was doing but I was able to do my eyelashes, added some eyeliner and lipstick. It looked sloppy but I didn’t think J would complain. The last bit was a quick spray of my mom’s perfume and then a terrified look at myself in the mirror. I took a deep breath and quietly exited the bathroom. As I slowly turned the door knob to my bedroom I almost turned around and backed out.

I opened the door just enough to reach my hand inside. As I found the light switch, I snapped it off and quickly entered my room and shut the door and blocked it with a chair. The room was dark but there was a streetlight just outside my window that illuminated the room enough for me to know J was laying in bed naked. His dark skin against the white sheets was a dead giveaway lol.

I took one more deep breath, got myself into what I thought was a sexy pose and I turned on the light.

“Holy shit!” J blurted out louder than I expected “..you look hot!”

It felt like a huge weight fell from my shoulders. I climbed into bed with J and his hands and mouth immediately went to work.

“Your perfume smells amazing!” J mumbled as he nibbled on my neck.

I began to softly stroke his cock which was rock hard! As he continued to nibble on my neck and ear, groping my breasts, the thought that tonight was the night started running through my mind.

“Let’s 69!” J begged

69ing had become our favorite thing to do together. We loved it because we were both being pleasures at the same time. It was a nice substitute for sex and we had gotten pretty good at it.

I flipped my position and got on top of J. We began sucking each other’s dicks and instantly everything that was going through my head prior went away. After a minute or so we rolled onto our sides but continued to 69. Mere seconds later I felt like I was going to cum. We both really enjoyed and tried for both of us cumming at the same time when we 69ed but this time I couldn’t help myself. I exploded in his mouth and it felt amazing!

As I finished cumming and continued to suck him off still in the 69 position, the thoughts about going a step further crept into my mind. I suddenly had this urge to be taken like a woman and I wanted to be fucked. However I was scared to say anything and instead I sucked his cock until he came in my mouth.

As we finished, I flipped myself back the correct way and we began to cuddle. Spooning to be exact. We made small pillow talk. He told me he liked the way I looked. He gently caressed my body and kissed my shoulder and neck. The more we cuddled and touched the more turned on we were both getting. His cock never fully softened and I could feel it swelling and getting harder as we spooned. J gently began grinding against me as his cock softly slid between my ass crack. I wanted him inside me so bad. I knew it was going to hurt and I knew it’d be uncomfortable and weird but I was dressed like a woman and I wanted to feel like one too.

“I’ll be right back.” I said I quietly got up and went to the bathroom

There was some KY lube in the bathroom cabinet that belonged to my parents and I snatched it and crept back into the bedroom and shut the lights off. I got back into our spooning position and J quickly returned to grinding and groping me. Still trying to work to work up the courage to hand him the tube of KY.

“I’m so in love with you.” J suddenly whispered in my ear

“I’m in love with you too!” I said turning my head towards him and kissing him

“I want you so bad right now!” J reaching up and squeezing my breast.

“Then take me.” I said handing him the lubricant

“Whoa, seriously?” He asked

“Mhmm.. I know it’s going to be uncomfortable at first but I can’t help it. I want you inside me!” I explained as I pushed my ass against his throbbing cock.

I had put a couple fingers in my ass a number of times to see what it felt like but J’s 8” black dick was going to be something completely different!

We stayed in the spooning position and J squirted some lube on his dick. He squirted a small amount in my hand and I wiped it on my asshole. Then J put his cock against my hole and pushed a bit.

“Oh god that hurts!” I moaned into my pillow.

“Should we stop?!” He asked frantically

“No! Just go slow ok.” I whimpered

Slowly J pushed again and again it hurt. The third push and the head of his cock slid inside me. I moaned into my pillow and wished I hadn’t offered. It was too late though. J knew he was inside and he slowly began to grind and thrust. In and out. Further in and out. Even further in and out. Each gentle thrust he plunged his cock deeper inside me. It hurt like hell but the more he moaned the more I knew he was enjoying it. The more he enjoyed it the more relaxed I got and the better it felt. Just as it was getting loose and easy, J squeezed my hip and clinched his muscles.

“Oh god I’m cumming!” He yelled

If my mom was awake she surely would have heard it. J pulled his cock from my ass and shot cum all over my ass cheeks. To

We cleaned up and finally exhausted ourselves and as we tried to finally fall asleep we talked about what we just did. Like everything we’ve done I wasn’t sure about it at first but when we were done, I loved it.

J fell asleep way before me and as I laid there all I could think about was doing it again. I loved everything about it, well except the initial pain. I loved how it made me feel. I knew I was pleasuring him. And I loved how close we were. He was actually inside me!

The next morning we woke up around 10am. I was still wearing the babydoll and there was makeup all over my pillow.

“You still glad we did that last night?” J asked

“Actually… I was thinking we’d go hop in the shower.” I responded with a kiss

J and I got up and made our way to the shower. Once inside we soaped each other up. Kissing and teasing each other along the way. On my knees I started licking the tip of his hard cock.

“You wanna fuck me?” I asked standing up and turning to present my soapy ass

I was so worried about our roles being so defined and now I’m suddenly so submissive to him. I had no problem being his “girlfriend” which is what he called me behind closed doors. I wouldn’t have done it for anyone else.

“Oh yeah!” J responded smacking my wet ass

This time bent over in the shower J’s cock slid in a little easier. It wasn’t long before his gentle pushes became aggressive thrusts! Feeling his thick black cock slide in and out of my ass was exhilarating! My face pressed against the bathroom wall. J’s hands firmly gripped on my hips as he shoves his cock deeper and deeper!

“Oh god, fuck J! Fuck me harder!” I cried “..make me your woman!”

J was lasting a long time and I was enjoying every second of it. I began to stroke my cock as well and literally seconds after a came all over the tub.

“I’m gonna cum!” J yelled

“Cum inside me! Cum inside me!!” I screamed

J thrusted his cock as deep as he could inside me and pulled my hips as close to him as he could. I could feel his cock pulsing as it pumped semen inside me! J let out a very primal grunt and he hunched over my back and kissed my shoulder. His leg was shaking at the knee and his toes had curled up

As J finally pulled his cock from my ass I felt cum leaking from my stretched out hole. We were both exhausted and surely the neighbors would have heard us.

Afterwards we laid in bed naked and just took a nap. We weren’t virgins anymore and we had a whole new world of sex to explore together!

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