Guess Who?

Guess Who?

Let me first begin by telling you that my step-mother Jennifer is a total babe. A sexy, full breasted, toned ass MILF. She has long dark red hair and nipples that will poke your eyes through your soul. When they pop, they really show. I jerk off to her a lot, and by a lot I mean daily, sometimes 3-4 times a day depending on what she may be wearing. And she doesn't care what she is wearing. My father is always away on business trips so it is not unusual for him to be gone for a few days to a few weeks out of town or out of the country even. Usually he takes Jennifer with him if he goes out of the country.

Secondly, Jennifer is unaware that I have been hacked into her laptop for over two years now, and I know all of their dirty little secrets. Dad and Jennifer video chat a lot when he is away. I actually think it's great, and I know they love each other. I know her computer front to back. I would know if she was cheating on him. I do know that he cheats on her. I have hacked his laptop before and I have the evidence.

Back to Jennifer. I adore her. I love her dearly. I want to fuck the shit out of her. That being said, I had long ago accepted the fact that it would never happen no matter what fantasy idea I had. But as long as her panties stayed in the hamper, I could be just a little close to her.

A little about me. I am 22 and I am a nerd. Not your typical nerd. I play sports, date girls, I hate chess and anime and I have a pretty good size cock. I am not john stud by any means, but 8 1/2" inches is a pretty good size. I love computers and I build them, fix them and can hack them. I am pretty good. I am attending college and live at home rather than the dorm since I have more room at home for my equipment.

Jennifer comes to me with her computer issues all the time. I was helping her one time fix an issue with her internet connection as it kept going out on her. I did my usual and checked for updates, conflicts and ended up just disabling the connection and enabling it again. Jennifer was leaning over me. I could smell her perfume and it was driving me nuts. When she rested her chin on my head and pressed her hands on my chest I felt precum dripping down my leg.

As we talked about what I was doing, her chat with my dad, which had been interrupted by the connection being broken, popped up and started downloading photos. Photos of her naked breasts and shaved pussy started popping up mostly, which were taken quite recently since she was wearing the same outfit as in the pictures. A photo of my dad holding his cock in his hand popped up and I looked away. I was happy to know though that I was bigger than him.

Jennifer was looking away. Her face was beet red. "It's...uh..fixed, Jen." I said, turning in the chair. I stood to leave and then stopped. She couldn't look me in the face. "Hey, if it helps ease this very awkward moment, you looked fucking great!" I told her winking. "Total spank bank material." I added. She smiled.

"Thank you, baby." she said. "Hey, what's a spank bank?"

"Look it up." I yelled back as I went upstairs and downloaded the photos to my computer.

I was upstairs, pants around my ankles, cocked lubed with astroglide and enjoying a long slow session with her photos open on my computer and a pair of her panties pressed crotch first against my nose when I heard her call out that she was leaving for the store. I listened for her to leave and the car back out of the driveway and let out a groan. I always had to be quiet and couldn't moan. I liked to moan. It added to the pleasure. Her panties smelled deliciously of her. She wore the sexiest silk panties and even those basic cotton panties (which I love by the way). There is something about those that drive me nuts more than any panty out there.

Anyway, I was slow stroking my cock to enjoy the sensations shooting through me as well as I love the feel of my cock. I love the curve and the thickness of it. I love the heat and the pleasure that comes with it. I was so wrapped up in it that I never noticed her standing in the doorway to my room. I don't know how long she was standing there. She didn't say a word or make a peep. She was like a fucking cat.

I was stroking faster and ready to cum and turned in my chair so I wouldn't blow a load all over my computer (I've done it before) and that's when I saw her. I opened my eyes as a wave of pleasure started, and saw her standing there. It was too late to stop and I ended up shooting hot jets of cum all over myself instead of the wad of paper towel I had prepared. She laughed as thick jets of cum hit me in the chin, the neck and all up and down my chest. I came hard too. It looked as if several men had just circle jerked all over me.

"JENNIFER!!" I cried out, starting to try and hide myself but gave up quick when I realized she had seen everything.

"So that's a spank bank?" she smiled. She looked at my computer to see her recent photos and pointed at them, and then saw her panties in my hand. "How? When? Do I even want to know?"

"I...uhh.." I had nothing. All I knew was that I was dripping with cum, busted, and probably homeless after this. But then she did the complete opposite. She reached over and slid her finger through a large splotch on my bare chest and brought it to her lips. She moaned and looked me in the eyes as she did it.

"Don't fucking move." She said and took her phone out. She took a photo of me holding my, surprisingly still semi hard cock and covered in cum. "This is for MY diddle drawer." She smiled. "I looked that up too!"

She tucked her phone back in her back pocket and looked at me still sitting there holding my dick. "Go get showered." She said, and pointed. I got up and walked like a scolded dog to the bathroom and showered.

I was in the shower when the door opened and she walked in. She opened the shower door and looked at me as she leaned against the wall. She was naked and looked me up and down. Her breasts were perfect and her nipples were pink and perky as she stood there contemplating. I dared not look down but it didn't take much and my cock was throbbing. She stepped in and dropped down to her knees. She looked up at me. "Not a word of this, baby, do you understand?" She asked. I nodded.

Jennifer took my cock and stroked it first, feeling it's thickness and it's length. She smiled and licked the underside of it before she leaned up and swallowed me down her throat. I groaned, bracing myself against the wall as her hot tongue and soft warm lips worked their magic on me. It's was far better than anything I had ever imagined. She caressed my balls gently and looked up at me as she drew her head back and kissed the underside of my cock.

Jennifer stood and switched places with me. She stood under the shower and got her hair wet. She smiled and grabbed the hair conditioner and squirted some in my palm. "Now," She said, "Jerk it off."

"What?" I asked, confused.

"Do you need a fucking invitation? Jerk it off, bitch." She said. Posing under the water.

I rubbed the silky creamy conditioner on my cock and started to stroke it as she touched her breasts and got them all lathered up. Her nipples stiffened as she pinched them. "You're father is in Japan until next week. You're going to be my little fuck bitch until then. If I say to do something, you do it. Clear?"

"Crystal." I said, pumping my cock. She watched me and as she did she slid her hand down to her smooth hairless pussy. She propped a leg up on the edge of the tub and slowly fingered herself. I was about to come. She could tell as my body twitched.

She dropped down and smacked my hand away and let the shower rinse the creamy conditioner off my cock. She took me in her mouth again and sucked me off until I came. She grabbed my hand and placed it behind her head as I twitched and jerked and as each shot of cum emptied deep inside her throat. She took every drop and then milked me when she pulled out and squeezed my cock like toothpaste tube until every drop was licked.

She stood up and showered and left me standing there. "Rinse off and meet me in the living room. Do not dress and do not wear a towel."

At this point I was scared. Horny as fuck, but scared. I've read stories like this where the man usually ends up getting ass fucked with a feather duster or some strap on dildo, and I am here to tell you that there is no way that is going to happen. I can take a finger, maybe two while getting a blowjob, but other than that, nope.

Jennifer was still naked when I got downstairs, but so were the others. Her sister Eileen, who was just as sexy, and someone that I have jerked off to as well. Her daughter, my step sister Maggie, who, at 19, looked just like her mom, and who has also inspired quite a few DNA drops. And then there was Jay, her homosexual friend. He was also naked. No fantasies there.

"Before you try to turn tail and run, they all know what you have been doing, baby, and they have come to punish you for it, BUT, in a good way, hopefully."

She pointed at Maggie. and Maggie stood up and blindfolded me.

"This is going to be fun, Darling." Jay said, his voice more feminine than masculine.

Jennifer walked up to me and put her hands on my shoulders. "You are going to pick a number between one and ten. Whomever has the number closest to yours is going to feel that big beautiful cock of yours up their ass. Are you in?"

I swallowed. "Do I get to know?"

"Nope. It could be me or my beautiful sexy sister or my scrumptious daughter or it could be Jay. He has a nice smooth ass too. I shaved it myself. You would never know. No touching either, Len."

"I'm in." I said, sucking up my bravery. I figured, if I couldn't see or feel anything but ass, I would never know. Besides, I would know if I heard a moan, grunt or groan if I were banging any one of the hottest women in my life or if I was banging Jay.

"Oh, and Len, any cheating, and Jay gets ten minutes with your ass. Got it?"

"Got it." I said, gulping. "How do we do this?"

Maggie walked up and touched my chest. "First off, you have to be really hard, Len, and right now you aren't." She kissed me, and I knew it was her and I could feel her tiny pert breasts and stiff nipples trailing down my chest until I felt her mouth on my cock. I was hard in seconds as she worked my cock and licked up the shaft. "Keep it hard for me, baby." Eileen shouted out.

"Give us a number, Lenny baby." Jennifer said.

"Eight." I said, and to my horror, everyone hooted and hollered. Chills ran down my spine as lube was poured onto my hand. I again sucked it up and stroked my cock. Despite the chances of fucking a dude in the ass, my cock was ready. I wasn't looking forward to it, but I agreed to participate.

I felt gloved hands guide me and position me and then mittens got placed on my hands. "You may hold hips, and just so you know, Jay has nice feminine hips, Len, you won't know."

I held the person and slowly pushed my cock forward. I was nervous and scared, but my cock was still rock hard I think from fear or the unknown, I don't know. All of them, in unison started to grunt and moan as they masked the sound of the one getting fucked.

I slid in nicely and it felt fucking good. The rectum of the person was nice and tight as I slid back and forth inside it. I groaned, picking up my pace and feeling my balls slap against cloth. I couldn't tell from this either if they would hit pussy or balls and at this point I didn't care as I felt my orgasm coming. Jennifer must have sensed it in me because she had me stop and pull out. She turned me around and had me wait while they all sat down.

After several minutes and my cock going soft. Jennifer washed me up with a warm soapy wash cloth and turned me back around. Her attention to my cock had me hard again. "Another number, baby."

"Four." I said. Again, everyone cheered. This time as I stood there, someone's lips wrapped around my cock. Magical lips and tongue sucked on me like a vacuum and licked me like and ice cream cone. Gloved hands touched my legs as someone took me back and forth down their throat until again I felt my balls tighten and they backed away. Another wait. Another number. Another round and then another.

This went on for most of the evening. I was allowed to eat, drink and rest the more we did it. At one point someone was sucking me off while another licked my ass and another French kissed me passionately.

I was spent and sat slumped on the sofa. Jennifer climbed up next to me and kissed me. She turned my head and licked my lips before pushing her tongue down my throat. I felt hands on my thighs and looked down to see Maggie and Eileen looking up at me as Maggie took my cock in her mouth. I was tired, exhausted, but these three goddesses had me going in no time. Maggie and her aunt kissed as they shared my cock. That was fucking the best image ever until Jennifer held her phone up and let me watch each session with each person. The first ass that I fucked was Maggie's. Jennifer even filmed her face as I fucked her and the look of utter pleasure on her face had me more than aroused. In the end I fucked all but Jay. He never participated. He video taped some of it but mostly jerked off or got blowjobs from the girls with his eyes closed. Watching myself fuck Jennifer and then Eileen's beautiful asses was pure heaven.

Another video she showed me was of Maggie bending Jennifer over and fucking her own mother with a strap on. Jennifer tossed the phone aside and slid up and presented her pussy to me. Her clit was large and ready.