An Anthology of Forbidden Erotica: 28 Depraved Tales

by Jessica Sin

  Other pictures showed her being fucked in different positions, both vaginally and anally, giving me a clear view of her private areas. In some of them she was naked, in some of the other pictures, she was beautifully dressed with her panties pulled down while being fucked. Some of the sets ended with close up shots of her face as she had an orgasm or with her mouth filled with cum. And some of the shots were close ups of her vagina with cum oozing out of it, both his and hers.

  Despite all of those various pictures in a variety of settings, they all had one thing in common, that although their faces didn’t show, all of the men in each set were different. Some of them were better endowed than others. Some of the men were white, while others were black.

  After flipping through all the explicit and vulgar images of Pippa on camera, it was the last set which really shocked me. There she was, in my room, on my bed, posing naked while someone took the pictures. Those photos were followed by the regular shots of her sucking a cock and then fucking, all while still on my bed. What the hell was going on? Why was she doing that in my room? But at that point, all of those questions which were swirling through my head were pointless because of how insanely aroused I was.

  ***

  I masturbated in her room while still looking through the pictures. I couldn’t believe my luck, finding where she kept her most personal belongings. I now had an incredibly intimate look at her sex life- literally. It was more than I ever could have hoped for, but at that same time, I knew my perception of Pippa would never be the same again, and neither would our relationship. But I didn’t care, it felt too good to stop. The taboo of what I was seeing was overwhelming. And before I knew it, I shot a massive load of cum, courtesy of my mother’s best friend’s very promiscuous sex life.

  ***A FEW HOURS LATER***

  I looked at her when she arrived home. She went from just being a kind of surplus mother figure to the woman I had desired most in this world. I now knew what every part of her body looked like in graphic detail, and what she looked like in every sexual position committing any sex act.

  As usual, we had small talk when came home, telling me how her day went while she was still wearing her sexy little skirt and buttoned up top. And afterwards, she headed back to her room. But a few minutes later, she came back and spoke to me one again:

  “Can you come to my room for a moment?” she asked. “There’s something important I need to talk to you about.”

  She turned back around and headed back to her room, still wearing her dress. I wasn’t sure what she was getting at, but I followed her as she wanted.

  ***

  “Sure, so what’s going on?” I replied, standing in her doorway.

  “The floor was a little damp around here when I stepped on it,” she said, standing by her dresser. “So someone had obviously been doing some cleaning. And I’m sure you know that I have a very good memory, so when I opened my drawer, I noticed that some of my more personal belongings weren’t exactly where I last left them- close, but not quite. You’re the only other person in this house. So…I believe you have some explaining to do.”

  I felt utterly humiliated. She caught me. And judging by the serious look on her face which I know all too well, there was no way of talking my way out of this, because she knew what I had been up to.

  “I…I’m sorry. I did it. I looked through your stuff.”

  “That’s all? You’re sorry? So you just woke up one morning and decided to go through my belongings? Come on, what aren’t you telling me?” she inquired harshly.

  “Fine. It started around two weeks ago when you were at the open house down the street. I went there to bring you a drink and I saw you with someone…having sex…and I couldn’t stop thinking about it since then.”

  “And my pictures?” she asked, still sounding calm. “I’m assuming that you’ve looked through them as well, and that the stain on the carpet was a little mess you’ve made in the process.”

  “…Yes…I’ve looked through them…” I reluctantly admitted.

  She smiled and said, “Men are all the same, you’ll sleep with or jerk off to any woman with a nice pair of tits and a vagina. But I can’t scold you for this since I’m the same way when it comes to men, as you’ve already seen.”

  “I couldn’t help it. Seeing you with that other guy was just an incredible sight. It changed the way I looked at you. You’ve always been one of the most beautiful women I’ve ever meet in my life, and I just needed to see something more. That’s why I did it.”

  “Well that’s really sweet of you to say despite the circumstances,” she replied. “And just so you know, I did my best to keep all of this secret from you.”

  “So who are all of those guys?” I asked. “I mean, are they all complete strangers, or men you’ve dated?”

  “It depends,” she replied casually, showing no embarrassment over any of this. “Sometimes I meet them online, our maybe while I’m out; it’s really not hard to find a man for sex.”

  “And what about the guy you had sex with in my bed, what category does he fall under?”

  She grinned, “You must have thought of me as a real whore when saw those pictures. I didn’t want to do it at first, but after the way he had been fucking me and making me cum, I just couldn’t say no to him anymore.”

  “Well, he’s one lucky guy if he gets to live out his fantasy with a woman like you,” I replied.

  “Now you must REALLY think of me as a slut, don’t you?” she asked jokingly.

  I smiled back and replied, “Of course not, we all seem to share the same fantasy now.”

  “Come here, get on your knees,” she said, seductively.

  “Why?”

  “Because you’re a handsome young man who’s been fantasizing about me; and since we live in the same house together, I might as well put you to use- that’s why. Now come over here…”

  I did as I was told and walked over to where she was standing, and got on my knees in front of her. Our eyes were locked onto each others as she reached down and pulled her panties off from under her short skirt and kicked them across the room.

  She held up the front part of her skirt to reveal a cleanly shaven vagina to me. The close up pictures on her camera did no justice as to how it looked in real life. Her labia was light brown and thick. Her clitoris was also fairly large compared to other women. And with the way she was standing with her legs spread apart, I could see that her pink insides were slightly moist. She must have been getting aroused during our brief conversation.

  “You’ve seen what you wanted, now start sucking,” she commanded.

  Once again, I did as I was told, leaning my head forward to touch the outside of her vagina with my tongue. She felt soft. Everything about her private area felt soft as I pressed my lips against the smooth surface of her skin. I took my time sucking on each side of her thick labia- relishing the moment while I listened to her moan. Once I was done with that, I used my tongue to rub her engorged clitoris, causing her to moan in pleasure even more.

  But being the woman she was, only sucking on the outside of her genitalia wasn’t enough. She used her fingers to spread her labia apart even further, inviting me to work on her insides. And I did, sticking my tongue inside her to taste her wetness. Her juices started flowing into my mouth as she started furiously rubbing her own clit while I continued licking and sucking her open vagina.

  Her moans became louder, and she stopped rubbing her clit to use her hand to hold her body up as she leaned against the drawer- she was having an orgasm. I continued rubbing her clit for her and using to my tongue inside her, but this time, instead of moaning, she let out a light scream, doing her best to keep her noise down. And as she did that, a strong stream of her fluids rushed inside my mouth and she screamed out loud as she came.

  As I finished licking and got back to my feet, she put her finger on my lips and said, “Not a single word about this to anyone.”

  And after she said that, she wiped her fluids from m
y lips with that same finger and put it in her mouth, smiling as she tasted herself.

  ***

  We continued this for the next few days. At any given time, she would let me please her orally. She was hesitant the second time we did it, but after a little convincing, she was quick to drop her panties for me so that I could give her another orgasm. And the days after that were practically routine where I didn’t even need to ask; she would come home feeling stressed after a long day, and when I asked if there was anything I could do, she spread her legs open for me.

  It was the perfect set up that we both enjoyed, one that I never would have imaged just a week prior. But of course, it eventually wouldn’t be enough for either of us.

  ***A STEP FURTHER***

  It was early in the morning before she went to work and I went to my college class. We were in her room and I watched, while still on my knees, as she wiped her vagina clean with a paper towel from me having performed oral sex on her.

  “I have a confession to make,” she said, after putting her panties back on. “I’ve told one of my ‘guy friends’ about what we’ve been doing- the one with the major fetish. You should have seen his reaction; it was priceless. It drove him crazy hearing about it. He’s practically been begging me for details ever since.”

  “I can imagine. A month ago I probably would have thought it was creepy, but now, I really understand this whole thing- obviously, since we’re doing this together.”

  “Look, I’ve been thinking, it may have been poor judgment on my part to ever get us started like this in the first place. Well not maybe- it was. I was in the heat of the moment with us talking about sex and finding out how much you enjoyed seeing me down the street with another guy and looking at my pictures; but now I feel like I’m just taking advantage of you. So if you want to stop doing this, I would completely understand, and frankly, it may even be for the best.”

  “Are you kidding me?” I replied. “I LOVE doing this. I know it’s weird, and, well, it’s not exactly normal, but I absolutely love it. But if you’re starting to feel guilty about me doing this for you, maybe you can, you know…help me out…”

  She raised her eyebrow and smiled, “Help you out? And what exactly are you suggesting I do for you?”

  “Well, you know what I mean. It would be nice not having to go back to my room and have to jerk off after taking care of your needs for you. Maybe you can help me out with that part.”

  “I suppose. Fair is fair after all. You can start by pulling your pants down, I haven’t got all morning,” she said, this time flashing a more mischievous smile.

  I didn’t hesitate to expose myself once she gave me permission. Even after all we’ve done together, it was still awkward for me being so exposed in front of her. But at the same time it was thrilling.

  She wasted no time wrapping her hand around my growing penis, rubbing it slowly at first- caressing it. But the harder I became, the harder she squeezed. And as my cock became fully erect, she knew exactly what to do with all her experience as she started stroking me.

  She never once looked at me while she started jerking me off. Her eyes were glued to her hand stroking my cock the entire time. I could only imagine what she was thinking, as she focused entirely on getting me off while having a serious look on her face. And it was becoming more and more clear that she was enjoying it almost as much as I did, because the harder I started to breath, the more intense she became with her hand, the harder she started to breath as well.

  Feeling the tight grip of her soft hand was amazing, but knowing that she enjoyed doing this to me sent me over the edge to a massive orgasm. She kept stroking as my cum shot straight up in the air and covered her hand as it came down.

  When it was all over, I watched in disbelief as she bent down and kissed the head of my cock. She then licked the cum from her lips and fingers before getting up and heading towards the bathroom.

  “Are we going to do this again?” I asked, still breathing heavy.

  She turned around and said, “I really need to wash myself and go. You know how much I hate being late.”

  She left without answering my question.

  ***AN UNEXPECTED SURPRISE***

  The following evening was the first time that she had told me that she was going out on one of her dates, which presumably was for sex. It was also the first day since I discovered her secret that we didn’t do anything sexual together. Before she left the house, she told me not to masturbate, insisting that she would take care of me afterwards while telling me of the details of her date to make things more exciting.

  But as it turned out, she came home about an hour later, and to my surprise, she came home with her date.

  “I didn’t plan this, but there’s someone I’d like you to meet, it’s the guy I’ve been telling you about,” she told me.

  “It’s nice to meet you,” he said to with a big grin on his face. “Pippa has told me about some of your recent endeavors together, and tonight, she has something even more special in store for you.”

  She took me by the hand and said, “Come on, let’s go to my room.”

  ***

  She continued holding my hand as the three of us headed up the stairs to her bedroom. No one said a word, but there was a sense of excitement in the air.

  Once there, Pippa had me face her while the other man sat on a nearby chair.

  “You’re obviously wondering what the three of us are doing here,” she said to me. “I’ve had a lot of sexual experiences in my life. But what we did yesterday with me giving you a hand job and eating your cum was probably the most nastiest thing I’ve ever done; it was also the dirtiest I’ve ever felt, even more than letting you eat my cunt. I don’t mean that in a bad way either. And when I met my ‘friend’ here for drinks and told him about all of this a while ago, he could barely contain his excitement and insisted that he watch us do more. I said no at first, but after a little convincing and a few more drinks, it sounded like a sexual experience that I just couldn’t pass up. So what do you say? Are you interested?”

  “…I am…” I muttered, not knowing what to expect.

  “Wonderful, now be a good boy and sit on the bed while your new in house lover gets ready,” she said.

  I sat on the bed and expected her to go and change or to do something first. But she didn’t. When she said she needed to get ready, she meant that she was going to get completely undressed where she stood. And that’s exactly what she did as she started peeling off her clothing, one by one, tossing each part of her outfit and each garment onto the floor until she was completely naked.

  She briefly modeled her nude body for us with her hands on her hips, turning her body side to side. And by the look on her face, she was enjoying the attention she was getting from us as it was appealing to all of our incest fantasies.

  “It’s your first time seeing my full body in the flesh like this- so what do you think?” she asked me.

  “I think you look incredible. I can’t believe I’ve been living with you for all these years and never thought to try and catch a glimpse of your body.”

  She smiled, “I’m about to give you something else you haven’t had yet…”

  She got on her knees as she said that and began pulling my shorts down. I moved my body a little so that my bottom could be removed, leaving me bare from the waist down. And almost without warning, she moved her head down and took my semi-erect penis inside my mouth for the very first time, making me instantly hard. Her mouth was warm and flowing with saliva. It felt incredible as her lips closed around me and she sucked as hard as she could while starting to bob her head up and down for a few moments.

  “Don’t let him cum just yet, I want to see you fuck him,” he said, while undoing his pants to masturbate while watching us.

  She stopped sucking and gave me a subtle look as if she was about to do something really nasty. It was clear that her hearing those words from him touched a nerve in her that maybe she wasn’t expecting. And clear
ly she loved it.

  She got up from her knees and pushed me flat on my back. She moved her legs and stood over me, just above my crotch, and held my erection up straight as she lowered herself onto me. She used her other hand to spread her opening so that my cock could easily slid inside of her warm and dripping wet vagina.

  “This is quite an experience for the both of us isn’t it?” she asked after she sat down on me and had my hard on buried inside of her. “I never imagined that my favorite sexual experience and partner would be with my best friend’s son of all people. And frankly, I’m glad that it is.”

  I didn’t have a chance to say anything back; I didn’t want to, as she began gyrating her hips, slowly at first, going faster with each thrust. She was fucking me the same way that I watched her fuck the guy down the street. The feeling was incredible. But what made it different from any of the other woman I had ever been with was how much she was able to squeeze her vaginal muscles together, making her vagina even tighter as she rode back and forth, while we kept looking into each others eyes.