Getting a job: Desperate: Proposition: Gentle
From Create Your Own Story
Tom walks up to me and brushes a few strands of my hair out of my face. I can't help but blush as he looks into my eyes. He leans in and I allow him to kiss me.
He is a good kisser, and the kisses distract me as his hands start to roam. Slowly a strap to my dress falls, then another, the dress falls leaving me in my underwear. If I knew this was going to happen I might have picked a thong rather than my skinny boy shorts, and a sexy lace bra than one of my normal ones. I get a little uncomfortable being so exposed and Tom responds by kissing my neck and then nibbling my ear, which starts to help me let myself go.
His shirt is the next piece of clothing to go. I can see how in shape he is, for an older man, Mr Hunter is quiet sexy. My hands explore his pecks and abs, while he waits for me to get adjusted. I turn around and let Tom unhook my bra. I instinctively cover my breasts, and then feel kisses on my neck and his hands pulling mine away exposing myself.
"Why would you cover those up? They're amazing." He says.
I respond "You don't think they are small? My friend Megan has much bigger..."
"They are prefect! You want what looks good for your body, and those aren't small either" as he says that he reaches around and grips them. He starts playing with my nipples and I start feeling hot. He definitely has experience with this kind of foreplay because you can't help but moan in pleasure, as he alternates between pinching, tickling, and messaging your perky gravity defying breasts. Before you know it his right hand slides down and starts rubbing your pussy through your underwear. "I see I'm doing a good job".
I continue to moan to his fondling and feel shocked when he stops. He takes my hand and leads me to his desk, I lay down on the desk and he slides my panties off. I look away and feel his tongue sliding up my folds, he finds my clit and jots of energy shoot up my spin. I have pleasured myself before but it never felt like this. His tongue feels amazing, but the mood is kind of ruined as he starts probing me with a finger. It is an odd sensation that I have never felt and I just can't relax. It gets even worse when he goes from one finger to two... I can't help but start wiggling my hips, Mr Hunter seems to think that's a good reaction but its not.
He finally stops and I finally relax, and lift my head and look down and see Toms raging hard on. I have seen a penis before, given my boyfriend a few hand jobs, but Toms dick was much longer that I had seen before. He spat on his hands and then smired it on his dick. "Relax, I still need to lube up" he said has I felt the tip of his dick kiss love box. He then started rubbing the shaft alongside my cunt picking up my juices. The anticipation was an odd mix of anxiety and curiosity. Tom went back to kissing me in various places and then pulled me to the edge of the desk giving his penis access.
I then felt him shift his dick into my outer folds. I closed my eyes and felt him press in. There was immediate tension and pain. I felt he made it in about two inches in and stopped.
"This is going to hurt", and he did a powerful thrust. There was a sharp pain as my hymen tore, but not as bad as I was expecting but still painful.
"OW!" I reacted. "Please go slow, it hurts"
It felt like he was slamming himself in me, while in reality he was going so slow that he was getting little out of it himself. Slowly but surely he was getting deeper and deeper in me, stretching me as he went. Not only did it not feel good, it sounded horrible as trapped gas He bottomed out and there was a sharp pain, he hit my cervix.
"OOWWW!!!" I yelped!
"Sorry, guess your not into it enough for me to go balls deep." he responds.
What started off as an acute pain subsides to a dull one as other feelings start to kick in. He seems to have a pattern where he has a few slow and long insertions and then a hard thrust. When he doesn't go deep it actually starts feeling somewhat pleasurable, but you can see its the deep hard thrusts that brings him pleasure. The longer it went on the more more he thrusted and the less into it you got. It then then turned into all thrusts, and once it was all thrusts he didn't last long.
"AHHHH Ahhhhh ahhhh" he moaned and then I felt hot ribbons enter me. I could feel him cum inside me as he collapsed on top of me. As I felt his dick shrink inside of me, I kind of underwelmed. Mid-way through it was actually pleasurable but only just, when he got rough the pain was just to much to enjoy it.
Tom finally pulls out and then slowly puts his boxers and then pants back on, "You know, you were my first, virgin that is."
This came to you as a shock, Mr Hunter was a catch, "Really?" feeling slightly insecure to the comparison "So was it special?"
Mr Hunter now is buttoning his shirt and says "It was special, I just wish I lasted longer, it was hard to hold back and you are REALLY tight." He then opens the door to his office bathroom and brings you a towel. He gently wipes the semen that leaked out of me and then helps me up. I'm still trying to process all that just happened and dress in silence, and that silence seems to unnerve Tom.
"You ok Lilly?" he says.
I break down, "I.. I.. I feel so dirty, I sold myself." and the tears start to flow.
He reacts very conforting and hugs me, "Lilly, Lilly, you did nothing wrong. I'm the bad guy here, I shouldn't have taken advantage of your desperation. You are saving your mother, that's a noble act."
His words somehow relax me, and I wipe away the tears.
He then says "Well, why don't you go home and get yourself cleaned up, I will see you tomorrow at 3:15"
He is surprisingly gentle
