Started with Panties
I was an 18 year old virgin with little hope of ever getting laid but I could jerk off with the best of them. That is how my sexual awakening started. After school, like clockwork I would speed home and invade my older sister's laundry. Claire was three years my senior and simply adorable. She had the look of innocence and the sheer confidence of an outright all star. I simply adored panties, hers in particular. She had a health build, meaning she wasn't wafer then nor bordering obese. Genetic be kind to her, gave Claire the most wonderful long red straight hair. Everything about her was almost perfect. Her lips were full, breasts and rear plump, eyes piecing and I long for a close equivalent. That stopped the second day of my senior year.
Entering my bedroom to prepare for my hamper dive I found an envelope on my bed. Within the brown manila envelope, to my horror were crisp clear pictures of myself adorned with a pretty pair of pink lacy panties strangling my cock. A lovely plain pair of white panties crammed in my mouth while my head was tossed back in orgasmic glory. After flipping picture after picture in what can only be described as total humiliation I found the note.
I must say when I first approached my humble room to find you bespattering my undergarments I was upset. But with time I have come to realize this was a cry for my help. I have the power to ruin your life with these pictures so if I were you I would do everything I was told to the letter. When I come home tonight your new life will begin.
Your loving sister,
My initial plan for the afternoon no longer seemed appealing, so I sat there in my little room with no idea what to think. I was caught by my sister masturbating with her panties, in her room, thinking about her. The pictures sat on my lap feeling like a two ton weight. Time helps in all things and after a few minutes I arose from my static craze and hid the pictures. I knew my parent would be coming home soon and I need to put on the "normal day" face.
My parent did come home and we did the family things. We ate dinner together, and then watched television. Promptly at 8:30 my parents went to bed and I was able to return to my reverie. For thirty minutes I watched the hands on the clock tick by and by.
I heard Claire come in the front door and she was talking to someone. Claire never forgot about a promise or a threat so hearing one of her bubbly friend chirping back to her made me believe, I had a few more hours reprieve.
Not a minute after I released a sigh, she entered my room. Her green eyes seemed to glow past her glorious red locks and her nipples were evident through the light tee she wore, and she was smiling. "Rob will you please come to my room so we can discuss our situation?" I froze hard, lost in what I was hearing she added, "Now." So I did what I was told. I followed Claire to her room.
I walked in and she closed the door. Her friend was sitting on her bed and Claire sat at her desk. She could see I was confused and before I could say anything she started, "Rob we have a bit of a problem. You, dear brother, are hopeless. Since I now realize you have been using me to get off for year and feel it is my turn to do the using. You seem a little confused so I will explain it for you. From now on you will do whatever I tell you, when I tell you or those pictures will end up in your school, your parent's hands, and in every business in a forty mile radius. Any questions?"
I stood mouth agape taking it all in, realizing my option were total public humiliation or personal humiliation. I gave what seemed like the appropriate response, "What do I have to do?" Again she smiled and looked at her friend, "This is Tiffany. Tiffany is a very curious girl who given current circumstance I am able to assist. Rob strip for us.
Immediately I was in shock and she said it again, "Now Robert." So I did what I was told. I kicked of my sneakers, slid of my socks, pulled off my shirt, and dropped my pants and boxers at the same time. I ware bare naked in front of my sister and her friend and Claire just smiled. Tiffany on the other hand was enthralled. Tiffany sat staring at my slowly enlarging member till finally Claire broke the silence, "Tiff you may explore to your heart's content. When you are satisfied we can move on to the other things we talked about." Turning to me, "Let her do whatever she wants."
Tiff was looking at my penis like it was a rare species of aardvark. She gently grabbed me, which led to rubbing, then surprise licking. I was in a hell of sensation, both emotional and physical. Tiffany looked back at Claire and Claire nodded. Tiffany a moment later engulfs my penis in her mouth and raked her teeth all the way down the length.
Tiffany stood up and for the first time I actually looked at her I realized she was really good looking. She was blond with blue eyes and a cute little nose. She was a definite second to Claire but she was nice to look at. While I made my observation she looked back at Claire and nodded which to my surprise brought Claire to her feet.
"Rob get on your knees." I went down and watched my incredibly sexy sister slowly strip her moderately sexy friend. I was in agony watching her shirt and bra disappear. Watching my sister's hands slide the girl's jeans then clean white panties down her thighs, past her knees, then off her feet were painful seconds. Slowly Claire set her on the bed with her socked feet pressed in tight against her thighs. Claire gave another satisfied smirk and looked at me, "I want you to crawl over her and lick her. I want her to cum hard. She has never been with a man so this shouldn't be hard for a boy like you."
I crawled as fast as I could and drove my face into her pussy like it was the last thing I would ever eat. The whole time Claire coached me, "Lick up and down... Aim for the little nub... Yes suck and hum." Claire was right; between my eagerness and her know how she came hard in minutes. The feeling of her juices covering my face and the sound of her gasping did allow me a small bit of pride but Claire took the right away.
Claire walked up behind me her crotch right at the back of my head and lifted her legs straight up. Looking down at me Claire spoke, "Good, now her asshole." I was already past the point of thought so I began lapping at Tiffany's tight little hole like there was no tomorrow. I licked, sucked, and tongue fucked that girl's ass for all I was worth. I don't know if she got off or not but Claire was satisfied and told me to go to my room, jerk off and take Tiffany's panties with me.
Once again I did what I was told and left her room to tend to myself. The next night Claire appeared at my bedroom door with the same smile, "Rob I have a new friend over and she would love to meet you would you come over to my room?" Knowing the routine I followed and as soon as the door closed I stripped. The new friend wore a short black skirt and a black tee shirt. Her hair was dark black and she was not in the least bit attractive. Claire told me, "This is Emma. Same rules as last night just do what you are told. One difference dear is Emma really doesn't like men."
Emma lifted her skirt to reveal a hairy bush and no panties. Pointing to the floor Emma began, "I want you on your back on the floor." I laid down and she began lowering herself to me face, "I have not wipe my dirty little pussy or my brown little shit hole so you are going to clean it for me. When you finish Claire will inspect your progress. If you do a good job I might give you a treat." With that she grinded her pussy over my face smearing what I would guess to be piss all over me. The aroma was horrid and the taste worse. I let her fuck me face till she was satisfied and she shifted forward, "Now the brown you little shit." Her asshole was crusted and I couldn't help letting little bits fall down my through. I was disgusted. But at least tonight it was over quick or so I thought. Emma rose from my face and bent in front of Claire. Claire shook her head and ran a finger down Emma's ass thru her pussy and said, "Horrible you may punish him. Rob please gets on your hands and knees for Emma." Emma sat behind me and grabbed my cock with force and bent it all the way back. Before I had a chance to adjust she shoved a finger up my virgin ass with no ceremony. I looked up to see I was facing Claire's seat. When she noticed me looking up at her she stood and stripped. I watched my sister sit, coat her middle finger in saliva, and push it slowly up her ass. Claire nodded to Emma so Emma would finger fuck my ass in time with her own ass fingering.
I watch my sister finger slide in and out while feeling Emma's finger. Emma suddenly removed her finger, again I thought it was over, and replaced it with two fingers. Emma pounded my ass with two then three fingers when finally Claire said, "That is enough for tonight." Emma ripped her fingers from my ass and as I tried to stand she shoved them in my mouth. I could taste myself on her fingers as she finger fucked my mouth. Satisfied with herself Emma Let me up and I went to my bedroom to jerk off again. I knew then this wasn't going to be over quick. I brought myself to climax as quickly as I could and passed out.