A night that felt so good but also so wrong. I was satisfied and wondering what the hell is wrong with my family?
I had a number of sexual encounters with Tony in the months after our first time. Once or twice a week for a few months he would randomly show up at my house after dark. We would go out to a shed I had in the back yard and I would blow him. We had to go out to that shed when my mom was home because she almost certainly would have heard anything we did in my room. The was a couple times when she wasn’t home and then I would let Tony fuck me.
I was really starting to enjoy the idea that I was gay. I absolutely loved wearing my mother’s clothes, and sneaking out to my shed to give Tony a blowjob was exciting.
Once Tony stopped coming over I found myself rethinking my sexuality. I was 16 now and even though I just had a secret fling with a man, and I still was wearing my mom’s clothes on a daily basis; I found myself still very attracted to women as well. Particularly my mother. So my focus returned to her.
It had been a while since she had come into my room to fondle me, and I was beginning to think that it was all over. Maybe she knew about Tony and assumed I was gay. My 16th birthday was the first one in 4 years that she didn’t come into my room. Just as I was starting the process of trying to forget about her “gifts” as she had started calling them… things changed, majorly!
It was a couple weeks after my 16th birthday and I was, as always, alone watching TV and playing video games. My mom was getting ready to go out to the bar with my aunt (her sister). I walked past the bathroom as she was putting her makeup on and all she had was a towel wrapped around her. She smelled so good. I already had plans to dress up in her clothes and have myself a night as soon as she left so seeing her in a towel and smelling her lotion got me super excited. Then, as I walked back to the living room, I caught her just at the right time adjusting the towel, giving me a quick glance at her breasts. She quickly covered herself again and finished getting ready.
About an hour later my aunt arrived. As I opened the door to greet her, she gave me a hug. It was a very awkward hug because I had a hard on from thinking about my mom. Thankfully she didn’t notice.. I think.. and they left for the bar.
As soon as their car was out of sight I ran to my mom’s room and started looking for something to wear. Now that I was older, her clothes fit me almost perfectly. We both were overweight and had similar builds. The only thing she had that I didn’t was D cups. I didn’t have D’s but I know towards the end of our fling Tony liked to play with and even suck on my boy boobs. It really turned me on when he did that!
This night I wore a pair of my mom’s satin panties. I slid some of her stockings up my legs and put on one of her bras. I would fill up water balloons to fill out the bra. I started watching some of my favorite porn while I laid in her bed playing with myself. That didn’t last long though and I came all over myself.
I sat on the couch in my mom’s black silk nightgown for about 5 minutes before I got up and went to the bathroom. I had been growing my hair long so I brushed it with her brush. I started to apply her makeup as well. Lipstick went well but the eye stuff was a disaster, lol. I jumped in the shower to clean myself, rubbing one out as well.
A few hours later I was lying in bed wide awake waiting for my mom to come home. Not long after I shut the lights off I heard a car pull up and my mom walk in. I popped out of bed and peeked down the hall expecting to see mom with some random guy she met but instead I saw her and my aunt. They were two women in their late 40’s giggling like two school girls. They were definitely drunk.
I laid in bed with my door open listening to them laugh and drink some more. They played some music and drank some more. I finally got up and shut my door hoping to fall asleep.
After an hour or so I was just about to doze off when my bedroom door opened. The music was still playing in the living room but as quickly as the door opened, a shadowy figure slid into my room and closed the door behind them.
“Are you awake?” She whispered as she sat on the bed next to me.
“Yeah. I can’t sleep.” I answered
“Sorry, we’re being so loud.” She said placing her hand on my thigh.
The scent of my mom’s lotion turned me on but I could no longer smell it as she smelled of alcohol and whatever bar they had gone to. That for some odd reason always turned me on as well.
Before I could say anything in return, a cold hand hit my knee and slid under my shorts and up my leg. My cock instantly began to swell and as soon as the cold hand grabbed ahold of my shaft, I let out a soft moan and placed my hand on her thigh in return. It didn’t stay there very long though because ever since seeing a fleeting glimpse of my mom’s tits that evening, I had been thinking about them nonstop.
My hand made it way north and grabbed a handful of breast. Something seemed off though. Even though she had clothes on, I could tell her breasts felt a bit smaller. Before I could even finish the thought, I knew exactly what was happening. It was not my mother sitting beside me. It was my aunt!
“What are you doing here?!” I blurted out
“Relax! Your mom sent me in here. It’s a late birthday present.” She whispered placing her hand on my chest and gently pushing me back down.
Seconds later my aunts cold hands tugged my shorts and underwear down to my ankles. Once again her chilled hand grabbed the base of my shaft and began to softly stroke me. At this point I couldn’t resist if I wanted to.
Suddenly she leaned over and I felt a wet warmth around the head of my cock. She had begun sucking on my dick! I couldn’t believe how incredible it felt. I lost myself in the moment completely and laid back and enjoyed the ride.
I had masturbated 4 times in the few hours they were gone so there wasn’t much left in my balls. I have no idea how long this went on because I was lost in the moment. Her warm breath clashed with her cold hand and sent chills down my spine! Her pouty lips slid up and down. Her tongue hit all the right spots!
“Ugh.. I’m gonna cum!” I said through clinched teeth
I could see her silhouette in the dark begin to bob her head up and down faster and faster.
“Mmm I’m cumming!” I groaned
As what little cum I could produce after now 5 orgasms in 3 hours started to spurt from my cock, her methods changed from hard and fast to soft and slow. Her hand squeezing cum out of me.
As she sat up, she swallowed the cum in her mouth. Still holding on to my cock, gently rubbing the tip with her thumb continuing the pleasure. The she leaned down and kissed me on the lips. It was a bit longer than a standard kiss and there was a small amount of tongue involved.
“Happy birthday!” She muttered as she stood up and quietly left them room.
I laid there puzzled but also satisfied and incredibly turned on! Why didn’t my mom do that? Why did she tell my aunt about us? Why did my aunt agree to this? I was so confused and I didn’t sleep at all that night.
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