Tom returned home from his second semester at Lyling Military University to find out that his mother and father would be gone for the next year to France leaving him home for his 2 week semester break alone with Deana; the Woman left in charge of the care of the house and to manage the servants until their return. This was not the news Tom had hoped for, Deana was a very strict by the rules woman. She was middle aged, had 2 children that had left home, and her husband had long been gone from the scene. 22 year old Tom on the other hand, wanted a break from strictness and rules. After 6 years in all male military schools he wanted to take the family Jag down to the local college and find a girl. 22 years old and he still was inexperienced. Tom had brief back seat romps, but never more than an awkward fumbling. It was time to do more and try all those things he had heard about, seen on the internet, but he himself had never expierenced. Plenty of lonely nights in a dorm room had led to surfing of web sites with images and pictures of people having sex in ways he could only fantasize about. He thought to himself all the wasted opportunity, I haven’t even ever had a woman touch my cock, nor have I ever touched a pussy or a breast. In fact Tom’s one and only partner was his ex-girlfriend Gina. Gina’s idea of sex was that she would pull her skirt up and let tom pump away till he was satisfied, but never any more than that and never did they get nude or explore each other’s bodys like he yearned too. Tom knew nothing of fore play other than what he had seen in the video’s. That was about to change, 2 weeks down at the local college with the senior class girls and he would be caught up, and have all his fantasy’s fulfilled.
Deana was not at all impressed that the Wilton’s had not mentioned that she would be babysitting every time Tom returned home on a break. Oh well there was only 3 breaks this year, and at the end of this school year Tom would be graduating and starting his enlistment in the army, besides how bad could it be he was 22 and should be pretty self sufficient. Plus he was not hard to look at 6 years of running and push up’s defiantly showed in the young man’s physique. At dinner that night, they talked about what had happened at school. Deanna was shocked to hear that the only free time Tom ever had was late at night after lights out, this did not leave much time for a social life. Something she had heard Tom’s parents mention he had no skills in. “So what are you going to do with your break then”? Asked Deana “I am going to take the Jag down to Trep University and visit some friends for the first week”. Said Tom. “Oh…..I am sorry Tom but the Jag Was sent to the shop for restoration last week, and your parents lent the Mercedes to your grand mother.” Replied Deana. “So you mean there are no car’s here, what do you get around in”? He replied in a very hostile tone. “Tom, I’m sorry but I don’t need a car here, if I need a ride I call a Cab, or today I borrowed a car from the Chef. I’m sorry Tom but I did not even know you were coming home till this morning. Now please finish up your dinner so that Sarah can get the dishes washed and get home before it gets too late.” As Deana left the room Tom shoved his plate away, very unhappy that his 2 weeks off would be spent walking the halls of his house with stiff old Deana. Just great. Later that evening the Tom sat and watched TV as Deana paid the estate bills. As the show ended Deana walked through, well I am off to bed. You can stay in your fathers’ business guest room. “Fine, thanks” Tom sat on the Sofa for another 10 minutes till he decided he was bored, he turned the lights off and went up stairs. As he neared the top of the stairs he saw Deana in the mirror reflecting from her room across the hall. She was undressing and trying clothes on. He saw her in a very nice silk teddy which she had been hiding under stuffy clothes all day. Tom thought to himself, for a middle aged woman she has a very nice body, in fact a devastating body. She put a dress on that soon covered her large breast and vivacious curves, bringing her back to the frumpy strict woman Tom knew her as. She then disappeared from the mirror and the door closed. Tom made the turn at the top of the stairs in the opposite direction and continued to his room. As Deana lay in her bed she thought to her self that Tom was a very difficult person, 6 years in military schools had kept him from developing socially, and he seemed to have very little care for others fellings. Perhaps she would arrange a car tomorrow so that he could visit his friends, which would probably do him some good. Tom entered the room with his bag and looked around it was a nice room with a large bed, a radio, a TV, and it was all his for 2 weeks. He thought this is funny it’s just like a large dorm room. Tom opened the closet to put his clothes away as he tried to put his last sweater away it hit something in the top of the closet. He looked and saw a small lap top computer. He pulled it down and recognized the tag on it immediately. It said Wilton INC.; it was his fathers work computer. Tom knew the rules, everyone in the house did. His father explicitly prohibited anyone from using it, the work files were very sensitive and his father could not risk losing them. He must have left it by accident before leaving for France. Tom put the lap top away, turned on his radio and crawled in to bed. 15 Minutes latter he still lay there stewing about not being able to venture out and enjoy the women of Trep University. How could his parents not leave him a car? Well they want me to stay here…fine then I am going to enjoy myself a little bit. He got up opened the closet and grabbed the lap top. On his way back across the room, he turned the radio up, to cover the noise of his plan. He removed his Pajama’s and crawled on to the bed naked, his 7 inches of man hood already beginning to swell with the anticipation of relief. As he logged on to the computer and began to surf he thought this is as close to a real woman I am going to get this year. He grabbed his cock and began to masturbate as he had for the last 6 yrs, watching the image of a woman masturbating and talking dirty to the camera filming her for his pleasure. Deana awoke to hear music blaring down the hall; half awake she sat and said to her self this is ridiculous. She got out of bed and put on the dress laid out for tomorrow, and went to the hallway. She immediately realized the music was coming form the guest room. As she approached the room she was so mad she did not even stop to think, and opened the door. There she saw Tom naked intently staring at a computer and stroking his cock furiously and awkwardly. In shock see stopped having opened the door just a few inches. She thought, right well, I’ll let him finish and he will go to sleep then, as she went to close the door she saw the Wilton INC. tag on the computer. Oh shit, how could she have forgotten Mr. Wilton asked her to send it to him two day’s ago. Now what will he think, he will see it has been used, and to watch Porn….he will fire me for sure she thought. Tom was in a world of his own; he never heard the door open, and all his attention was on the buxom blond about to orgasm on his screen. He feverously pounded away waiting for his release, but it just wasn’t happening. Great he thought, now I can’t even get my self off. Suddenly he saw a shadow move across the door and saw it was open……Deana he thought, the music must have woke her. Oh well his room mate had caught him before and it did’nt bother him then….in fact he thought why stop, let the old bird get a peak, maybe she will loosen up if she gets to see some cock. He refocused his attention on matters at hand and at the computer screen. Deana was totally lost; she knew she had to stop him, but how embarrassing for the both of them this will be. She knocked twice on the door with her head down and heard nothing. Tom lay on the bed ignoring the knocks. Deana Knocked again, and heard nothing. Right fine I have to go in Deana thought, she slipped through the door quietly trying to avoid eye contact with the muscular naked man stroking his hard cock in front of her, but it was hard to avert her eyes. “Thomas” she said. “What” replied Tom? “Can you please stop for a minute please” said Deana. “No” he replied. Deana was shocked ……what to do now. “Tom you can not use that computer for anything, especially for…..that, you know that”. Tom sighed and said “well what else am I going to do around here”? Deana was flustered, she didn’t know what to say, and with out thinking she replied “Tom you can do that all day long…I don’t care but you will have to use your mind and imagination, not your fathers’ computer”. Tom stopped and his mood changed immediately, he closed the computer and looked at Deana. “What do you mean”? For 6 years I’ve had to this quickly before some one intruded on me, I don’t have time to imagine it”. Suddenly Deana felt sympathy for Tom all his schooling had prevented him from enjoying his own body. Deana sat down and asked Tom “have you ever been with a girl Tom?” “Of course” he replied. As Tom covered him self with a sheet he explained how he had the 2 minute fully clothed romp with Gina his ex a few times. Deana thought this poor man……”Ok Tom, I’m sorry but your life so far has prevented you from learning some very pleasuring lessons”. Deana felt for the boy but this was awkward, her own life had started much the same but then in her early twenties she discovered the joy of sex with her husband. She had enjoyed about every possible sexual aspect she could for 10 years till her husband was killed 5 years ago. “Ok Tom this is awkward, but I think we need to teach you to use your mind and enjoy your own sexuality and not hurry through taking the time to enjoy yourself ”. Tom was stunned he actually was starting to feel a little awkward himself now. “Ok” he replied “what do you want to do, shall we fuck”? “No Tom, No, you need to know yourself before you can pleasure someone else. “Ok then what” said Tom. “First turn off the computer and hand it to me”. Tom lay on the bed as Deana sat in the chair, not able to believe she was doing this. “Tom close your eye’s and lay back on the bed, imagine one of you cam girls laying on the bed next to you slowly masturbating, look at her body, here her moans”. Tom’s cock immediately sprang to action. Deana was amazed, it was beautiful a nice large specimen, one she would salivated over in her younger day’s. “Now Tom slowly rub your cock, imagine her touching it” Tom immediately went from slow to furiously stroking. “Slow down Tom…Slow Down” Said Deana. “I can’t, I can’t I want to cum” said Tom. “Tom it is not just about the orgasm, it’s about the experience, the greater the stimulation the greater you’re orgasm, and hers will be”. Tom Suddenly felt Deana’s hands on his, slowing down his stroke, it felt odd, it felt good, but at the same time he felt his desire inside building, not just his cock wanting to explode. Deana was beside her self, she could not believe she was doing this, but he needs help she said to her self. She saw Tom seem to settle down and enjoy the slow teasing play, and his cock just kept getting harder. “That’s good Tom, now keep thinking about her body, her voice, what does it sound like. Deana was so hot at this point she decided she had to go soon, she had a vibrator she had not used in years in her dresser but tonight it was definitely going to be put to use. “What is she like Tom?” Tom never answered he was just breathing heavy and lost in his own mind. That was good he has found his imagination thought Deana, but Deana was ready to explode now too, she could feel her pussy was absolutely soaked. Her nipples were hard from the rubbing, that’s when she realized Tom’s hand was massaging her tits through her blouse. She looked down and didn’t even realize she was so caught up in the moment that Tom was no longer stroking his cock, she was. She thought oh well what will it hurt if we turn each other on a bit, she unbuttoned her blouse and pulled a breast out and placed her nipple to Tom’s lip. Tom immediately sucked on the hard nipple, she was amazed how he enjoyed it he slowly massaged her breasts and Deana felt a hand running up her skirt. Deana thought ok I have to stop this, or do I? Maybe Tom should learn it all tonight, Gawd knows I have not had a good fuck in years, and oh how I have missed it. “Tom, how do you feel?” Tom replied “I can’t explain I just want to explode inside…all of me”. Deana knew this feeling; in fact she felt it right now. She stepped back and said “Tom you are ready for more” She unbuttoned her blouse and dropped her clothes to the floor, Tom Stared in Awe. Deana laid down naked next to Tom, he looked in amazement he had never seen a woman nude in person. She was beautiful. Tom thought she looked good earlier in the hallway, but he realized now how amazing she was in full form. Her breasts were soft and subtle with large hard luscious nipples, her curves flowed endlessly and her neck yearned to be kissed. Her pussy was beautiful. Deana obviously enjoyed keeping it trimmed and Tom could see it glisten with wetness in the light. He approached her and they kissed passionately, Deana continued to slowly rub his cock, and for the first time Tom was allowed to touch and rub a womans pussy. She immediately let out a soft moan, which tom took as a signal to heighten her pleasure, he kissed her neck down till he found her nipples flicking them twice with his tongue before sucking them gently. Deana continued to moan and breathe heavily. Tom thought this is it; this is what I have been missing. Deanna sat up with a new look in her eyes, a look of lust, she slowly lowered down and took Tom’s manhood in her mouth. Tom felt as if he would explode, he had never felt this, and while he was only rubbing Deana’s back, she acted and sounded as if she was on the verge of cumming her self. Tom thought I have more to do than finish here. He pulled Deana up and kissed her. “Deana I want to do the same for you, but I have never done that”. Don’t worry baby it will come naturally” said Deana. With that Tom disappeared between Deana’s legs. Tom knew nothing of female anatomy, at first he just kissed her pussy, till he found her clitoris Deana pulled his head forcefully on to it, and he realized this was the spot to stay on he sucked on her clit, and stroked her nipples with his finger’s. Deana was on fire almost gasping for air. Deana was in ecstasy , gawd he was good but she yearned to be penetrated. That is when she felt tom slip a finger in to her wet pussy, gawd it felt good, he fumbled about a bit then all of a sudden she felt something she had not felt in years, he had found her G-spot. Yes” she screamed yes keep doing that. Tom was amazed, was this the same woman he had dinner with. He thought not. Her body almost seemed to convulse. Her moans were now screams. Yes, yes tom … I’m‘Cumming. Tom Felt Deana’s body convulse and then almost go stiff at the same time he felt her pussy tighten and then she seemed to relax and every thing subside. Tom thought that was it, she would be done now, and he had missed his enjoyment, but nothing could be further form the truth. When he returned to his pillow he saw Deana with a look that almost scared him. She was a woman possessed. He had seen this look before with his sparring partners at the academy, he realized that there they were out to kill him. Deana had a different agenda, she intended to fuck his brains out, and she did not hide it. “Tom, tonight you will experience every thing you have ever wanted. With that Deana sat on top of Tom and guided his manhood in to her. It felt differently than when he had been with his ex. It was hotter, wetter, and defiantly more explosive. Deana was insatiable. She would fuck and cum almost like a machine. The two spent the next hour trying about every position tom had seen his movies and then some he had never. Finally almost exhausted he found himself on top of Deana, she was moaning and yelling “cum on me Tom Cum on me”. Tom felt his balls stiffen and an orgasm building, but it was moving slower, but felt more powerful then he had ever felt before. Finally he knew it was the final moment. Deana could see it in his face she knew it was Tom’s graduating moment. She quickly pushed him off her and took his manhood in her mouth for a moment then with a quick 2 or 3 frantic strokes, she felt Tom moan and his cock spasm, as his spunk covered her breast’s she rubbed it around her nipples almost like suntan lotion, savoring every little drop . In the end Tom’s cock went limp, he was exhausted, and she was exhausted. She climbed from the bed and Tom said “thank you”, she in return said, “No Thank you, I have been denying myself that for years”. Deana said “I suppose I had better go”, not really wanting to leave. Tom stopped her at the door “if it’s not too much, I would really like it if you stayed in here tonight”. Deana almost felt a tear swell in her eye, the two retired to the bed that they had turned into a love shrine for the previous 2 hours. The both quickly drifted off to sleep. In the morning, Deana awoke in a panic. It was 9 AM she usually started her day at 6. She quickly showered, dressed and prepared her self then ran down stairs. As she stepped on to landing she smelled fresh bread and saw fresh cut flowers. She saw Tom pouring Coffee and buttering some toast with 2 places at the table. “Thank you Tom, said Deana. Tom replied this is the least I could do, my first day home was the best night of my life”. Deana blushed. “Tom I thought we would go rent you a car so you can visit your friends” “Thank you Deana, but I think I would prefer to stay home during my break”. Again Deana blushed. Tom this could be awkward, the servants don’t go home till late, so we have to be careful all day long” “I know “said Tom….That’s why I gave them all the next 2 weeks off.