Saturday, October 13, 2012


I hadn’t had a real date in a few months, so I had really been looking forward to tonight. I had been introduced to Tom through a mutual friend and we hit it off pretty well. I had almost forgotten what it felt like to be stared at and admired like that, but when I saw Tom from across the room, I could see him watching me. The smile on his face told me he liked what he saw.
Tom wasn’t the first older man I had dated. In fact, my ‘first’ was an older man. His name was Jim Masterson. I call him my first, but he wasn’t the first boy I actually had sex with. There were a couple others before Jim, but he was the first one that knew what he was doing, and the first man to really fuck me.
I grew up in a small down in the Midwest. When it came to boyfriends there weren’t very many options to choose from. I was taller than most other girls and I let my hair grow long. Boys didn’t notice me until my breasts started showing, but by the time I was a senior in high school, I had turned town every boy in town…except for maybe two or three.
I had gone to college the summer before I started to decide if it was the place for me. The campus was huge and I felt completely out of place. Even in the summer time there were lots and lots of people walking everywhere. I must have looked as out of place as I felt, ‘cause that’s when he found me. I was sitting alone on a bench wondering what I was going to do next when I saw a man walking towards me with a grin. I watched as he got closer, and wondered who he might be.
“You must be new here.” He sat down next to me and held out his hand. “Let me be the first to welcome you to our little campus. My name is Jim Masterson.”
“Hi…Maggie, my name is Maggie.” I shook his hand and was surprised at how long he held my hand in his. He seemed to almost caress or squeeze my hand gently as we talked. “Was it that obvious that I don’t belong here?”
“Everyone feels awkward their first time. You are new here and don’t know your way around. You don’t know anyone here yet and so it’s only natural for you to want to go back home where all your friends and family are. Don’t worry though, that feeling will pass and soon you will have all the friends you could ask for. A beautiful young girl like you shouldn’t have any trouble fitting in here.”
“That’s true.” He kept his blue eyes on me the whole time he talked. I hadn’t even noticed how close he was sitting next to me, but with his deep voice and that smile of his, I didn’t seem to mind at all. “I’m not alone anymore. I mean I know one person now so that’s progress.”
“Yes Maggie, you now have one friend here and that is a very good start. Why don’t I get you started on your tour and point you in the right direction.”
“That would be great. I’d really appreciate that. I didn’t realize there would be so many different buildings.” I showed him my map I had and the different buildings I was looking for. He explained the best way to get around and things to avoid while navigating my way around. After all his help, he made one more offer that took me by surprise.
“When you are done here, give me a call. Here’s my card. I’d love to take you to dinner and answer any questions you might have.” Jim handed me his card and again placed my hand in his as we said goodbye.
“I will do that. Thank you Jim for being so nice. I don’t know what I would have done without you.”
I called him a few hours later and he picked me up shortly after. He wanted to stop at a local bar before dinner he said and so we parked in a back alley and went in the back door.
“A good friend of mine owns this place. You’re gonna love it.” He opened the door and let me through a dark narrow hall into a back room.
“Jim…wait…I’m only nineteen. I don’t think I’m supposed to be in here.” I didn’t know if I said that in case he didn’t know, or if I wanted to make sure he knew I was…legal, but either way I told him and he only smiled and told me not to worry about that.
“I tell you what Maggie. I won’t hold it against you that you are nineteen, if you don’t hold it against me that I am twenty nine. Deal?” He took a couple glasses from behind the bar and grabbed a bottle of wine. If he hadn’t told me the bar belonged to his friend, I would have assumed this was his place.
“Deal,” I answered back acting a little shy, “I’ve never gone out with an older boy before. I hope you’re not trying to get me drunk then have your way with me Mr. Masterson. I’ve been warned about men like you.”
“Don’t worry Maggie; those are not my plans at all.” He handed me my glass and waited for me to take a sip. “You will be completely sober when I have my way with you. I want you to remember every minute of it.”
I was completely caught off guard with his words and before I could response, he leaned in and kissed me. His lips felt so soft and smooth against mine. He licked my tongue with his as if tasting me and my glass nearly slipped out of my hand. I felt his hand slide around my back and pull me in tighter against his body as we kissed deeper.
“I think we need to skip dinner, Mr. Masterson.” I felt a sudden warmth flow through my body as I whispered the next few words. “Is there someplace more private we can go to?”
“You are full of surprises Maggie. I know just the place, and might even have a few surprises for you before the night is over.”
We drove around town for a while before he finally pulled into a hotel parking lot. I expected him to take me to his house or an apartment, but not to a hotel. He opened the car door for me and held my hand as we walked in the hotel. He didn’t sign in or even talk to the girl behind the desk, but headed straight for the elevator.
It seemed a bit surreal for me to be here with a man I had just met, but it felt good. It was exciting to feel his hands on my body as we walked down the hall. It felt exhilarating knowing this older man found me attractive and wanted to be with me. He made me feel good.
“Before we go in Maggie, put this on.” He pulled out a scarf from his pocket and began folding it. “Don’t worry; I’ll take good care of you.” He wrapped the blindfold around my head and adjusted it until I couldn’t see a single thing in front of me. I heard the door open and his hands grabbed both of mine. “Follow me in.”
The room felt colder as I took a few steps inside. He led me further into the room then let go. A few seconds later I heard the door shut. I turned in circles trying to get a feel for where he was, but I couldn’t tell. I couldn’t hear him anymore and didn’t want to walk around and run into anything, so I held still and called out for him.
“Jim…where are you? Where’d you go?”
“I’m right here Maggie,” his familiar voice whispered directly in front of me. I felt him move closer then felt his kisses once more. His hands began unbuttoning my shirt while he kissed me. I tried to get his shirt off, but he held my hands back. I stood there with my hands to my side as he undressed me slowly. His lips kissed my neck gently as my shirt slipped off my shoulders and slid to the floor.
He moved behind me and quietly removed my bra and then my belt. He knelt down behind me and slid one shoe off, then the next. He placed his hands on my waist and gently moved down my body, taking my pants down at the same time. His lips pressed against my ass and kissed me a few times as I stepped out of my pants. Then his fingers played with the band on my panties, and then slowly pulled them down also.
“You are amazingly beautiful Maggie. You are stunning. Let me look at you for a few minutes.” The room got quiet again and I could hardly stand still. I could almost feel his eyes admiring my every curve. My hands moved gently over my skin as I touched my breasts for him. I imagined him smiling at the sight of me holding my full breasts in my hands…gently tugging at my nipples while he watched. I was wondering how much longer he was going to make me wait, or how much longer I would be able to wait until he touched me again, then I felt it.
His strong hands grabbed my waist from behind and pulled me against his naked body. His lips moved down my body as again he knelt down behind me. He spread my legs and slid one hand up against the inside of my thigh until his fingers rest against my moist flesh. He moved his fingers back and forth against my lips with one hand, while the other reached around and rubbed my clit. His finger easily slid between my wet lips and slowly began fucking me. My hips pushed back harder…wanting him deeper inside me…wanting to feel his cock inside me.
He must have been reading my mind, and soon stood up behind me and let his hard cock slip between my legs. His hands again grabbed my waist and pulled me back closer against his body. I bent over a little and grabbed his cock as he moved back and forth against my pussy. My wrapped my fingers around his cock and felt how wet he already was, and couldn’t but feel how wet my pussy already was. I rubbed the head of his cock against my clit a few times, and then pushed him inside me.
He stood still as I pushed back against him, taking him slowly inside my tight pussy. He moved gently at first. He took his time and gave me a little more of cock every few minutes. He felt so big inside me. He was definitely bigger than any other boy I had been with. I wanted to look down and see his thick hard cock sliding in and out between my tight wet lips, but remembered the blindfold.
“That’s it baby,” I whispered as he began moving faster. “Fuck me faster Jim…give it all to me.”
Soon I was taking every inch of him inside me over and over again. He grew harder and longer as he fucked me faster. My body grew weaker as he held me tighter in his hands and began pounding my pussy with his rock hard cock until I was ready to cum. I squeezed my nipples between my fingertips and moaned out his name a few times…”I’m ready Jim…almost Jim…Keep fucking me Jim.” Something about hearing my voice say his name made me closer and closer to cumming.
Then he kissed me.
“Trust me Maggie,” he whispered and kissed my lips. He pulled the blindfold off of me and I found him standing naked directly in front of me. He held my face with his hands and kissed me again. “Don’t turn around…trust me Maggie…cum for me Maggie.”
I wanted to turn around and see who was behind me. The truth was at that exact moment, I didn’t care who was behind me. I was getting fucked like never before. The man girls like me only dream of was standing in front of me kissing me. In the darkness I reached down and found Jim’s cock hard and ready. I began stroking him as the cock inside my pussy picked up speed again.
“Cum for me baby,” Jim whispered again and as if on command it hit me. He didn’t stop fucking me, but kept moving fast and hard. I could feel my lips almost vibrating against his cock, until he quickly pulled out. A few seconds later I felt him cum all over my ass. I could almost still feel him inside me and wondered what it would have felt like to have him cum inside me.
I could hear someone breathing heaving behind me. Jim leaned into me and held my nipples between his lips. He kissed my breasts and slid his hands around my sweaty body. Suddenly the lights turned on. I looked over to the door and found the stranger standing there…my new lover…an incredibly good looking man with a strong muscular body. He only smiled at me as I stared down at his big beautiful cock. He grabbed a towel and came back to me. He stood behind me gently whipping my cheeks and my back as he kissed my neck as if saying thank you.
“I told you I had a few surprises for you tonight Maggie. This is the friend I told you about…the one who owns the bar.” Jim led me to the bed and sat me down. I still didn’t know what to say or think about what had just happened and Jim knew that. “You were magnificent Maggie. You have no idea how incredibly sexy you are. Just watching you move and listening to you…wow…just amazing.”
He kissed me again with his soft smooth lips and looked at me with those eyes I had only just met this morning. I moved up in bed and lay down with Jim still at my feet watching me. I pulled my knees up and spread my legs and smiled at Jim. He didn’t make me ask twice, and soon his soft lips were gently sucking on my pussy. His tongue danced against my clit and soon I was ready to cum again. My fingers tangled through his hair and pushed his mouth tighter against my clit as he licked me faster. I looked around for Jim’s friend but didn’t see him in the room anymore. I almost wished he was there again so I could see the huge cock that had just fucked me.
“That’s it Jim…you’re gonna make me cum again…don’t stop…” My voice gave out as he rubbed the underside of his tongue against his clit from side to side until I came in his mouth.
“Mmmmmm,” Jim moaned as he kept licking me slowly, “Damn you taste good Maggie.”
I was ready for his friend to come back. I was waiting for both of them to line up and ask me to suck both of them. I was ready for them to take turns fucking me over and over again all night long. I was not ready for what happened next.
Jim kissed my pussy softly a few times then moved up my body. He kissed my stomach a few times then gently licked my nipples. He moved up over me and moved the tip of his cock against my clit. He teased me with his cock for a minute until I wrapped my legs around him and pulled him inside me. He moved slow and steady inside me. He never took his eyes off of me. He kissed me and whispered in my ear every minute or so.
“You look so beautiful Maggie. I’m so lucky to have found you today.” He slid his cock deep inside me and pulled completely out. Over and over again he fucked me like this and I wondered if he was ever going to cum. I could feel him throbbing stronger and stronger inside my tight pussy the longer he went, but still he fucked me long and slow. “You just don’t know how special you really are, do you Maggie?”
“I bet you say that to all the girls Mr. Masterson.” I joked and wrapped my arms around his neck. “Mmmmm…but I bet you don’t kiss them quite like that…you do know how to make a girl feel special.”
He kept kissing me as finally he picked up speed. My body lay beneath him getting hotter and hotter. With the lights turned off again and our eyes locked together, he fucked me fast and hard for another minute, and then stopped deep inside me. His lips parted as he came inside me and he smiled down at me until he was done. I pulled him back inside me with my legs as he tried to escape, and let my pussy squeeze every last drop before letting him go.
“That was…well, that was…amazing. I had no idea sex could be that good.” I said as Jim lay down next to me. “I don’t know what that was.”
“That wasn’t sex Maggie. Anybody can have sex…anyone can simply fuck…but there are no words to describe what you and I just did.”
“I wonder what other surprises you have in store for me in the future. I have a feeling you and I are going to be seeing a lot of each other next semester.” I rolled over on top of him and smiled down at him. “You didn’t tell me you were Professor Jim Masterson…who teaches philosophy…first period…which I have.”
“I think I will be giving you a lot of extra credit this year.” Jim wrapped his arms around me and held my head against his chest. I thought about how much I had changed in just a few hours. From the naïve young schoolgirl who literally stepped off the bus that morning, to the woman I had become this very same night.
“I think I am going to love college.”
As it turned out, I did love college and have many cherished memories from my younger days…my wild and crazy days. The doorbell rang and so I stood up and opened the door for my date with Tom. Just thinking about Jim and his friend these last few minutes had gotten me excited and I only hoped Tom had the energy to keep up with me tonight.
“Hello Maggie, you look great tonight,” Tom started in the usual way before I turned the tables on him.
“Change of plans Tom. We’re not going out…we’re staying in.” I grabbed him by his tie and led him straight to the bedroom.
Copyright 2011 Damian Santiago

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