An Anthology of Forbidden Erotica: 28 Depraved Tales

by Jessica Sin

  At 26 years old, my best friend was a very beautiful girl. She’s about as classy and as elegant as they come. Her shoulder length light brown hair has natural waves to it which adds a sense of modern style to her. She also has a stern face which suits her career in law, she justs seems so powerful sometimes. Physically speaking, her 5‘4 frame makes her a pocket rocket, with pert breasts along with having a shapely rear end which she likes to jokingly blame on all the horse rides we took together when we were toung..

  She didn’t date much since we started living together. I never asked her about it and she never brought it up. But it was obvious that she was always too busy for someone else in her life. She constantly worked long hours as she was a very hard working and disciplined person. And when she did date, it was never more than a few months for whatever reason. I’ve always figured they weren’t good enough for her as she never seemed that enthused about any of them.

  ***ONE PARTICULAR EVENING***

  One day out of the blue, Silvia had announced that she would be going out on a date later that evening, which was unusual because it was a Monday. Usually she approaches dates like she does her work, where she plans it for the weekend and lets me know far in advance showing very little enthusiasm over it. But this time was different; it seemed like she didn’t know about it until the last minute and told me only when she arrived home. She seemed very excited over the whole thing, an excitement which I hadn’t seen in a very long time from her regarding other men.

  “So how do I look?” she asked me with a huge smile on her face while modeling her outfit to me.

  I wanted to tease her and tell her that she looked like she was going back to work because she wore what seemed to be her normal business attire of a professional two button jacket, matching color skirt, and thick panty hose. The only difference was she wore a little more make up and jewelry. She looked classy as always.

  “Great!” I told her. “No man would be able to resist you tonight.”

  She smiled and gave me a hug; she loved those kinds of compliments. She sat by the window for a Silviaent and as her date pulled into the drive way. And when he did arrive, she immediately opened the door for him before he could ring the bell, which was a first for her.

  Her date was also professionally dressed and seemed like a nice guy. ‘Finally, someone who would be a great match for Silvia,’ I thought. He did seem very nice when Silvia introduced us. He came across as a complete gentleman and it turned out they meet each other a few months ago at work, and only in the past few weeks had they been starting to have lunch and spend more time with each other on a regular basis.

  “Don’t forget, dinner is in the fridge, and when I get back I’m going to check to make sure you finished all your vegetables,” Silvia said in her best friendly tone. “Oh, and by the way, don’t worry about me, we might be a little late tonight, but please leave this light on as well as the light outside so I don’t trip over anything, you know how clumsy I get.”

  “I was planning on sleeping early tonight anyways, I have class tomorrow morning. Enjoy your date you two!” I said as I waved them off.

  I was very happy for the both of them, and I was especially glad to see Silvia as happy as she was. Especially considering that I was considering moving out soon to attend graduate school to become a lawyer like she is. It would be nice to know that my best friend is with someone she’s happy with.

  ***

  I planed on calling it a night and hitting the sack early not long after dinner. But it was just one of those nights where you’re sitting on the couch watching TV and one thing pops up after another and before you know it, you’re eyes are glued and you don’t want to get up.

  It was almost midnight when I heard Silvia and her date pull up in the drive way. I thought that was surprising considering she normally comes home from a date around 10 or earlier, even on weekends, let alone a day before work. I turned off the TV and was getting ready to open the door and turn the lights off for her so we can both go to sleep. But oddly enough, I never heard the door open from the car, even a minute after they arrived. I figured they were still talking after a nice romantic night out and I decided to check on them through the front window.

  I peeked through the blinds and I was stunned by what I just saw, or what I think I saw. Silvia’s date was lying back in his chair with his eyes closed, but she wasn’t in her seat. It looked like his hands were rubbing something in front of him but I couldn’t see what it was. Was this really what I thought it was?

  I had to get a better look and I immediately ran up a flight to stairs to see them from Silvia’s bedroom window, which had a direct view of the drive way. My suspicion was correct; my best friend had her head buried in his lap and was performing oral sex on him. From my angle, I had a clear view from what was going on (thanks as well to the light from the front door). I could see her head bobbing on his crotch while he was holding her hair from falling over her face. When he pulled her hair back for a second time, I saw her more clearly. Her face looked nearly caved in from how hard she was sucking. And those same lips she uses to kiss me goodnight had formed a tight O shape around this guy’s erect penis.

  I couldn’t believe what I was seeing. All my life I had seen my best friend as someone who was stern and proper in everyway. She always scolded me whenever she heard me use the slightest curse word or do something she considered immoral. She always presented herself in the most elegant and professional light, and here she was sucking some guys cock in front our house like a common street whore.

  Despite the fact that she was my best friend, I found myself becoming incredibly aroused. Just the taboo of what I was seeing amazed me. Seeing her in the middle of a blowjob was amazing. But that woman being my own best friend made the whole thing 10 times dirtier. My penis suddenly became harder now than it had been in a very long time.

  I couldn’t control myself anymore, I pulled my penis out and started masturbating to my very own best friend sucking cock; watching her head bob up and down, seeing her face smooched together with a dick inside it.

  I was stroking my hard penis watching this go on for a few more minutes before I saw his body tense and his head lean back. It was fairly obvious that he was about to cum. I expected Silvia to stop sucking and maybe jerk him off or something, but she didn’t. She kept on bobbing even as his body arched which obviously meant that she swallowed his cum. All of what I had just seen was more than enough to make me shoot a large load of my own cum into a tissue I grabbed near her bed. The orgasm I had was so intense that I felt as if I had just gotten laid.

  I saw his flaccid penis for the first time as my best friend took her mouth off him and sat up straight in her chair. He was still laying back in ecstasy after what he had just received from her. My best friend was saying something to him with a smile on her face, and he laughed. Being the elegant woman that she is, she pulled out a small packet of tissue from her purse and used it to wipe the excess fluids from the sides of her mouth as if she had just finished a meal. She also pulled out a few extra pieces of tissue and bent over to clean his penis for him as well. How nice of her.

  Despite just having a massive orgasm of my own, my mind was still in a sexual frenzy. As she got out of the car, I couldn’t just go to my room and pretend to be a sleep. I still felt the need to see more, to do more to fulfill my recently enraged hormones. As I heard her open the door, I ran back down to greet her so I could see the aftermath of their sexual encounter.

  “Hi Silvia!” I said, still breathing heavy from running.

  She gave me a look like she wasn’t expecting to see me. “Oh, hey sweetie. I didn’t expect you to be up this late, I thought you’d be in bed by now.”

  “I couldn’t sleep, just wanted to check up on you and see if you had a good time and came home safely,” I said with a deviant smile.

  “Well that was awful nice of you, you didn’t have to. And I had a great time by the way. Can we talk about this tomorrow? We should both be getti
ng some sleep at this time of day.”

  As she walked past me, she gave me a small pinch on the cheek along with a wink, which she occasionally does. But this time was different, she was different. Her hair looked like it had been thrown all over the place, it looked sloppy. Her red lipstick was smeared around the inner parts of her lips, leaving only a red line on the outer parts. And she had a slight odor of sperm to her. It looked like she was hiding what was in her other hand by making a tight grip and holding it away from me as she walked away, and for good reason to, it was filled with the other guy’s cum, which I decided to tease her with.

  “What that in your hand?” I asked pretending I didn’t already know.

  She genuinely looked surprised that I had asked causing her eyes to slightly widen. “Oh this?” she said as she waved them in the air. “It’s nothing; I had allergies on the way back home. Must have been the pollen, we went out for a long walk after dinner.”

  ***

  With that, both of us headed back to our rooms to sleep. But I couldn’t sleep, I had to jerk off again thinking about what I had seen this evening. Silvia was giving someone a blowjob in our drive way. I couldn’t stop thinking of the sight of her elegant face being filled with a cock, and her sucking and bobbing on it. I kept replaying that last conversation we had, along with that look on her face. She looked like such a whore with that messed up hair and smeared lipstick. With that outfit she looked like a high end escort. I loved how proper she was wiping that cum of her face and off his penis. Even with sex she was so proper.

  I kept stroking thinking about all those things for about 20 minutes. What sent me over the edge with another orgasm of the night was thinking about what she was doing. I could imagine her lying under her covers fingering herself to sleep thinking about how she whored herself out like that. I imagined her eating the cum off that tissue before flushing it down the toilet so she could taste him one more time.

  I came again. I had ‘regained’ my senses and my mind returned to normal from all those deviant sexual thoughts and images about my own best friend. The feeling of guilt came over me as I laid in bed reflecting on what I had done and the thoughts I used to bring myself to cum again. But at the same time, I knew this wouldn’t be the end of it. The feeling was just too amazing to stop.

  ***THE NEXT DAY***

  I couldn’t stop thinking about what I had seen the night before. How something I wasn’t suppose to see turned my entire life upside down. I might as well have stayed home all day, because in all of my classes, I just kept thinking about my best friend performing fellatio on her new date. Obviously I shouldn’t have been surprised that my best friend enjoys sex as much as everyone else, she is human after all, but seeing her perform a sex act was still obviously a major surprise. I changed my entire perspective on her and I had felt a level of sexual arousal the likes of which I’ve never felt in my entire life.

  All of which had got me thinking further; what would become of all this? Would this change my relationship with my best friend for the worse? Would I keep jerking off fantasizing about her? And more importantly, would I be satisfied with just my imagination if I were to pursue this?

  I knew right then and there the answer was to all of that was no. I couldn’t stop, and I didn’t want to. I had to find a way to see her; see her with her boyfriend, see her nude, see her masturbating- whatever it takes to fulfill my newfound sexual desire for my own best friend. At least I hoped so.

  ***DINNER***

  It felt a bit awkward that night for both of us given the previous nights circumstances. I decided to break the ice by talking about one of my new favorite topics, her new man.

  “So how was it last night between you and him?” I asked.

  She gave me a look like she didn’t know whether I was talking about the actual date or making an innuendo that I had known what she had done in the car (I was doing both).

  She smiled after that brief pause, “It was great, we had a nice meal followed by a lovely walk around the downtown area, and we stopped for ice cream. We had a chance to speak briefly earlier today at work, I’ll be seeing him again soon for another date.”

  “That’s wonderful Silvia. I’m glad you’ve finally found someone you’re happy with. Maybe next time you could invite him over for dinner. We can all get to know each other better, and after that I’ll be so quite in my room you two wouldn’t even know I was home.” I said with as much charm as I could.

  “Well there’s an idea,” she replied. “He can try my cooking and both of you can get to know each other a lot better. And if you couldn’t already tell, I really like him, and he really likes me. So hopefully, this turns out to be something more…long term…if you know what I mean…”

  I reached out and patted her on her shoulder. “I do Silvia, I do. And he does seem like a great guy. You two are a perfect match, unlike those other guys you’ve been dating.”

  “Thank you. You have no idea how happy it makes me to know that you approve of him.”

  ***TWO NIGHTS LATER**

  Well…make that two very long days later. I really couldn’t wait for him to come over to our house. I did want to meet him, but more than anything, I wanted another chance to see (or hear) them in a sexual setting. This was really the only way I would ever get to see her performing a sex act of any kind or to catch an intimate look at one of her body parts, because after all these years of living with her, I know that she is always very cautious with covering up her body.

  Dinner finally came and it was everything I expected it to be. We all had a great time chatting and he and I got to know each other a lot better. Sylvia had an ecstatic look on her face the entire time as if she were in love with him and was delighted that I had taken so well to him.

  I cleaned the dishes after dinner as they went to the living room to watch tv and talk. Afterwards, I made a point of saying goodnight to them and to announce that I would be headed to bed already because I was exhausted and needed to wake up early the next day. But of course I really just wanted them to do something while they thought I was asleep and I would find way to watch.

  I laid in bed with the lights off surfing the internet for about an hour- then it happened. I heard a soft moan- then another. The faint noise was coming from the air duct. My imagination started running wild with the any number of sexual scenarios they could be up to, in our own home of all places. There was no way I was just going to sit in my room and listen, I had to go and watch.

  I opened the door quietly, and walked gently across the hall so I wouldn’t make any noise. Most of the downstairs lights were turned off and the living room lights were dimmed allowing me to hide in the shadow while being able to see them. As I got close to the stairs, I laid my body down on the floor and stuck my head out slightly so I would have a clear view of the living room.

  I was stunned at the sight of them having sex on the couch, completely unaware that I was watching them. He was sitting there with his pants down, and Silvia was on top of him, bare from the waste down facing his direction. I became more and more aroused watching Silvia slowly gyrate her hips in a circular motion while they both looked incredibly aroused, planting kisses and rubbing their hands on each other in between their soft moans.

  I couldn’t believe what I was seeing. Even though I had hoped something would happen for me to watch, I never would have imagined that my best friend would ever be so brazen as to have sex with someone on the living room couch while I was still home. The same feelings of lust and taboo of watching my own best friend overwhelmed me as it did a few nights ago. The more Silvia thrusted her hips against his erect penis, the more aroused I became.

  My eyes began fixating on her bare bottom as they continued to have sex as it was first time in my life that I had seen any of her intimate body parts. I watched in lust as her voluptuous full sized rear end clenched every time she was vaginally penetrated. It was as if her bottom had a life of its own as its muscles constantly contracted causing it to jiggle in the
process. She then started to gyrate her hips faster and in a more intense motion making both of them start to breath harder.

  “Shhh…Shhh…” she whispered, putting a single finger on his lips to make sure he kept quite as they were both headed towards an intense orgasm.

  His body tensed up and he reached down and used both hands to squeeze the flesh on my best friend’s ass as hard as he could while he came. My best friend looked like she had an orgasm as well by the way she clenched her hands and feet and flung her body forward, pressing herself onto him. Then suddenly, they both relaxed their bodies onto one another. They both started smiling as they began planting kissing on each others lips. I watched in pleasure.

  “That was amazing,” he said, still breathing heavily. “Of all the places we’ve fucked, this has to be my favorite; in your living room while your son is upstairs sleeping.”