I became obsessed with the girl next door and did things I’d never imagined to get off
When I was 7 my mom and I moved into a new duplex. We lived in the downstairs unit and in the upstairs unit was a mom, her daughter and son. The daughter, Melissa, was the same age as me and the son, Joe, was a year younger.
I was immediately obsessed with Melissa. She wasn’t the most gorgeous girl ever but she was the girl next door, literally and figuratively.
By the time we got to middle school my obsession was in full swing. I would watch her sun tan in the back yard. I befriended Joe, even though I didn’t really like him that much, have sleep overs at his place knowing Melissa wasn’t going to be home, then say I had to pee and go in her room for a minute and look in her underwear drawer. The major force behind my obsession was by the time we reached 9th grade, Melissa had 36D breasts. The grew so much in high school that she went as far as breast reduction surgery just to even things out a bit.
Joe and I were hanging out regularly in high school. In middle school we started experimenting sexually. We would watch porn and then giggle, and eventually work up the courage to take out our ducks and rub them. We would masturbate together just about everyday after school. It always started off with pretending we were professional wrestlers and we would “wrestle” in our underwear. The physical contact always got us worked up and eventually we would take out our cocks and play with them.
The first time I saw his dick I didn’t know what to think. It was considerably smaller than mine. Not bragging but I have a 9” cock. Joe on the other hand wasn’t much bigger than an adult thumb. 5” and not much girth.
For the longest time all we ever did was masturbate together. One day I got brave and reached out and took his little cock in my hand and stroke it for him. After he came all over my hand I asked if he’d do the same for me. He reluctantly agreed and stroked my cock. It was hard to concentrate because he was giggling about how much bigger my cock was in his hand than his own.
This went on for months, just jacking each other off. It was great actually. I would go into a fantasy world and pretend it was his sister, Melissa, doing it.
This only fueled my obsession with her. I was hell bent on being with her. I would do anything! Our duplex we lived in shared a laundry room and I would quietly sneak in there while her clothes were being washed and try to steal some of her underwear. I took one pair the first time. Another the second time. I didn’t think she would notice but by the third time I had taken another pair of panties and one of her bras. It was the bra missing that caught her attention.
There was a knock on my door. I opened it to find Melissa and her Mom standing there asking me if I knew anything about it. I made up a lie. I don’t know how believable it was but it appeared to work. I told them I heard someone in there and assumed it was her and thought nothing of it.
Afterwards I immediately retreated to my room and put her panties and bra on. My cock was so hard and standing straight up sticking WAY out of the panties. I started stroking myself and I came instantly.
The next day Joe and I were up to our usual antics and he asked me if I took her underwear. He told me that he didn’t care, and that he wouldn’t tell on me. He even admitted that he would wear his moms panties and lingerie sometimes while he masturbated.
I admitted that it was me that took them but I told him if he told anybody I would beat the shit out of him. After reassuring me he wouldn’t, we proceeded with our antics.
His story about his Mom got me thinking about my mom and her underwear drawer. I called Joe and told him to convince his mom that he was sick and needed to stay home from school the next day. I would do the same.
After both our moms went to work and Melissa went to school, I ran upstairs and knocked on his door. I convinced him to let me look in his mom’s underwear drawer. He pulled out a few things that were fairly sexy but nothing that wowed me. So I went into Melissa’s room despite Joe telling me not to. I was rock hard but I didn’t see anything that I hadn’t seen before and knew if anything else went missing I’d be in trouble for sure.
Joe and I went downstairs to my place and I took him into my mom’s room and showed him somethings I had found in her drawer. There was a black and red lace teddy and a blue silk nightgown with black lace trim. There were some black stocking and a garter belt to hold them up. Then I pullled out the dildo I found. It was a giant 12” monster! We laughed a bit and both held it for a minute or so before putting it back.
I took off all my clothes and nodded to Joe hoping he’d do the same. He did. We both stood completely naked in my mom’s room when I put the blue silk nightgown on. I pressed my body against his and asked him if it felt good. Joe just kind of moaned a bit. At this point I was so fucking horny that I would’ve done anything at that moment.
I reached around and squeezed his ass cheeks and kissed his neck. He continued to moan a bit. I was so turned on that I just wanted to see how far I was willing to go. I kissed him on the mouth a couple times. He didn’t fight it so I stuck my tongue in his mouth this time. Still no fight. I had stroked his cock so many times that it wasn’t anything new. I got on on my knees in front of him and started stroking his dick.
I knew what I wanted out of this but I knew what I had to do to get it. By this time in late high school, Melissa was just a pipe dream. She was popular and I was not. My fantasy to be with her would just have to be her brother.
I took a deep breath and opened my mouth. I wrapped my lips around the tip of his dick and slid them down his little shaft. Joe let out a loud moan, as if years of stress just left his body. The last time I was this bold and started stroking his cock, he returned the favor. I had hoped he would do the same this time.
About a minute into giving my first awkward blowjob I felt a spurt of cum shoot down my throat. I knew the taste because I tried my own cum a time or two just to see what it was like. Another spurt hit the roof of my mouth and when I realized I didn’t hate this, I got more into it. Stroking and milking every drop I could get out of him.
Despite my best efforts I could never get Joe to return this favor. Even when I was in my senior year and he came out as bisexual I couldn’t get him to dress up and blow me. I continued to give him regular blowjobs in hopes he would change his mind. I always dressed up for him too. Now, still feeling like a straight guy, I enjoyed dressing up in women’s clothes and pleasuring him. I started buying lingerie and women’s underwear online and sleeping in it every night. Realizing that Joe returning the BJ one day was probably not going to happen, I changed my fantasy and how I went about it.
When I would pleasure him, whether it be blowjob or handjob, I would imagine that I was Melissa and he was me. At first it wasn’t great but then I lost myself in the fantasy and it became amazing.
I devised a plan to go all in with this. I went online and found a whole new outfit and underwear set. I bought black bra and thong set. Next a pair of black stockings that went halfway up my thighs. I swiped a pair of my mom’s high heels that were too small for my feet but I forced them in. Then I bought a tight, white halter top shirt that exposed my belly and a pair of girls jeans that I cut into short shorts. Lastly I went on a Halloween website and found a wig that most resembled Melissa’s hair. When all of it arrived I put it on and stood in front of the mirror. I was so turned on!
After telling my mom was going out to the bar I asked Joe to spend the night at my place Friday night, I got myself prepared for everything and anything. Joe came downstairs and I let him in. I told him to go to my bedroom, I had a surprise for him. I had a backpack with everything I needed in it in the bathroom.
On my bed was a pair of my jeans and my football jersey with a note that said “put these on. Tonight you’re me”
I took my time getting everything on. The tiny A cup bra I wore was tight but held my pectoral muscles well. The black thong came on and I hid my throbbing cock as best I could. I put the shorts on and it held my manhood in place. Next the stockings and high heels. I slipped the halter top over my head, put the wig on and took a deep breath. I slowly exited the bathroom and crept toward my bedroom. I cracked the door ever so slightly to see if Joe had done as I asked. He did. He was standing in the middle of my room wearing my football jersey and favorite jeans. One more deep breath and I opened the door revealing myself to him. Joe’s eyes lit up and his jaw dropped a little. I closed the door behind me.
“Do you like it?” I asked
“Mhmm” Joe replied
“Tonight you’re me and I’m your sister. Call me Melissa.” I explained
Joe nodded in acceptance of my demands taking a step towards me.
“Say it! Call me Melissa!” I demanded putting out a hand to stop him until he did as I said.
“Melissa.” He said pushing my hand aside.
Him calling me Melissa sent a sense of joy through my body. I approached him and started kissing him on the neck and then making my way to his lips. I called him by my name and sense of joy returned in my body. There was a wetness on my tip of my cock and my thong. Pre cum was leaking out.
“My pussy is so wet for you!” I whispered to him going with the fantasy.
I reached my hands up the football jersey and pulled it over his head. Kissing his chest a few times and even biting on his nipples. I was gonna do everything I wanted Melissa to do to me tonight.
I pulled my shirt off and unhooked my bra. I guided his head to my nipples.
“Suck on my big titties!” I told him.
While he lightly nibbled on my nipples I started unbuttoning his jeans and pushed them down. I reached down and grabbed a hold of his cock.
“Wow, you’re hard!” I told him. He was in fact quite hard. Harder than I had ever felt him before.
I undid my jeans, dropped them to the floor and kicked them aside. I slid my tongue down his chest and stomach until I got to his cock. I wasted no time in taking it in my mouth. I was getting much better at giving blowjobs and he was lasting much longer now. I sucked his tiny little cock for about 5 minutes. I could taste small drops of pre cum from him now. It was time to go further.
I stood up and dropped my panties. I took his hand and lead him to the bed where I laid on my back. He seemed unsure of what was going to happen but instinctively got between my legs. I grabbed a small tub of vasoline that my mom had in her drawer and stroked some on his cock. What was left I wiped on my asshole.
“Fuck me!” I told him as I put my legs up exposing my hole.
He didn’t seem to get it so I grabbed his cock and placed it on my hole.
“Are you sure?” He asked
“No. I’ve never done this but there a first time for everything.” I explained “Just slowly push it inside me and do what I say.” I continued
If his cock was as big as mine or even a little smaller I don’t think I would’ve had the courage to try this but in my preparation for tonight I did put a finger or two up there to see what it felt like.
He started pushing. I instructed him to push harder since it wasn’t going in. He gave one solid thrust and the tip of his cock popped in my ass.
“Oh shit!” I moaned
“Does it hurt?!” He asked
“Just a little. It actually feels good.” I told him “..just go slow.”
He started pushing it in deeper and pulling it out.
“Oh fuck it feels good when you pull out!” I told him
He started going slow and deep, as deep as he could, and pulling out fast, all the way to the tip. Every time his tip hit the area where my prostate was it felt amazing!
“You can go faster now!” I told him “..go faster! Fuck me!” I demanded.
He wrapped his hand around my upper thigh and grabbed my pelvis pulling me closer to him and started thrusting harder and faster. Strings of cum were now dripping from my cock as it slapped against my stomach with each of his thrusts.
“Jack me!” I demanded
He took my cock in his hand and started squeezing the cum out of my cock. I couldn’t believe how great it felt! It felt so amazing that I lost myself in the fantasy and called him Joe.
“I’m gonna cum! What should I do?!” He asked
Just cum inside me Joe!” I moaned
He thrusted two or three more hard ones and then stopped. I squeezed my asshole around his cock and I could feel it pulsing and hot cum spurted into my ass. When he was done he pulled out and sat back on his heels. Cum still trickling from his tip and more leaking out of my ass.
“Oh my god! Why did we wait so long to do that?! He said out of breath
“That was so much more pleasurable than I thought it’d be.” I told him. “I came so much.” I continued
We got cleaned up by taking a shower together. Surprisingly nothing happened in the shower but after we got out and dried off, I put on some of my lingerie and crawled into bed with him. I cuddled up next to him.
“You want me to do that sometime for you?” Joe asked
“Well yeah, but no pressure. Like I said, that was way more pleasurable than I thought it’d be.” I told him
“How so?” Joe asked
“When I came it felt like I was having 5 at once! Your dick inside there just felt really amazing.” I explained
“Maybe I’ll try it sometime then. We’ll see.” Joe said
“No pressure. I’ll still do that for you.” I said “so, we’re gay now?” I asked after a moment of silence.
“I don’t know, are we?” He asked
“I don’t feel gay. It was just getting off I guess.”
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