The following story is based upon a true story. The story itself is largely fictional, but parts of the scenario are based upon true events or environments.
Vanessa and Tom had dated for quite some time. Vanessa was Tom's "first" sex partner and Tom was Vanessa's second partner, but really more like her first (her first experience was a short-lived unfulfilling stumble of an attempt at sex). After dating for a few years, Tom had enlisted in the US military and was due to go to boot camp in about 3 months. Vanessa was completely supportive of this and when Tom had returned home after boot camp he proposed to Vanessa, to which she gladly accepted. The only obstacle was Tom's first duty station was overseas for one year. They thought this will be a good test and if they survive it, they will get married immediately upon his return to the US. There was no doubt in either of their minds that they would not survive life apart. Boy were they wrong.
Vanessa lived with her mother and her stepdad, in a rather large house. They rented out two of the rooms and a makeshift room in the basement to a few middle-aged tenants (Denise, Jonathan and Daniel).
Denise really plays no part in this story, but she was the longest termed tenant and she acted as a nanny to the children throughout the years. She was in her mid 50's and she generally kept to herself in her room knitting or reading a book.
Jonathan was about 35 years old and had shoulder length straight brown hair that he could comb back into a pony tail or could let down and looked pretty handsome. He liked to play sports of all kinds and was very sociable.
Daniel on the other hand was in his early 40s and was a bit rougher around the edges. He was not very attractive and was slightly overweight. He was very kindhearted though and knew how to tell some jokes.
Tom knew these tenants and did not perceive them as a threat. They never said or did anything inappropriate to either himself or Vanessa. If only he had known then what he knows now, he would not be so trusting or naïve.
What he doesn't know is that Jonathan (the tenant who rented the makeshift bedroom in the basement) has always had feelings for Vanessa since she developed into a woman, but due to her being under the age of 18, had been very strict about not acting upon these feelings. But now that she was over 18 and her fiancée was going to be out of the picture, for at least 1 year, this was his opportunity to act upon his feelings.
Vanessa was a very beautiful young woman. She had developed a large 34 DD chest with an hourglass figure with a booty that just begged one to smack that ass. She had long wavy dark brown hair and her lips put Angelina Jolie to shame, they looked as if she could suck the chrome off a trailer hitch with little effort.
The first couple of weeks after Tom left, Vanessa was very lonely and depressed. Jonathan could sense her loneliness and felt it would be the key to him entering her world, sexually. Her love was still very strong for Tom though and Jonathan knew the time was not quite ready. So, he remained in that "friendly" stage biding his time before he would make a move.
Vanessa would hang out with Jonathan and Daniel (who rented a room upstairs), especially on the weekends. She did not want to go out with her friends to nightclubs. She felt this would only make her miss Tom more and would even possibly send the wrong idea if word got back to Tom that Vanessa was out clubbing while he was defending his country overseas.
There was a pool table in the basement and an electronic dart board. There was also a sofa set and Jonathan and Daniel both played guitar and they would often "jam" together, much to Vanessa's delight. It was really helping time go by and she was getting more and more relaxed and comfortable.
One night, about 3 months after Tom's deployment, the three of them (Vanessa, Jonathan, and Daniel) were hanging out and drinking some beers. Not getting too drunk, but loosening up, nonetheless. They had played a few rounds of pool and darts and Jonathan suggested a jam session, but Daniel declined. He said he was getting a bit of a headache and should call it a night as he retired to his room upstairs.
Jonathan and Vanessa sat downstairs and just talked about random things. Jonathan would get Vanessa to talk about her relationship with Tom and he (Jonathan) would play the consoling shoulder to lean on. When he sensed her getting sad, he would guide the conversation to positives about their history. He would inquire upon things like how they met (as if he really cared it was all just a guise) and then he would guide it into sexual topics, like was Tom her first partner and how did she like the sexual relationship with Tom.
Through this conversation Vanessa admitted that she was not very confident in her oral sex capabilities. She said that Tom loves blowjobs, and particularly wants her to deepthroat him but she could not avoid gagging and that she was very worried about puking if she pushed it too far. Furthermore, she does not like cum, especially in the mouth.
Jonathan viewed this as the perfect opportunity to take advantage of Vanessa and he had set himself up perfectly for it. Her inhibitions were lowered by the alcohol and her defenses had been reduced by his consoling behavior that she was totally trusting of him. Even so, he was still a bit nervous of taking that first step, what if he misjudged her and she blew up on him? Would he be evicted out of the house and be on the street? What would he do if that happened? But he decided it was now or never...so he jumped.
"You know now might be the only opportunity to fix that? And what a perfect opportunity it is!" Jonathan stated as he chuckled nervously awaiting her reply
"Opportunity? For what? What do you mean?" she replied as she turned her head towards him waiting for him to elaborate.
"Don't take this the wrong way, I am not trying to be a homewrecker or some creep. I am just trying to be a friend to you both." Jonathan replied.
Vanessa looked intently as Jonathan continued.
"I am offering you no strings attached blowjob lessons. I won't tell anyone, if you don't tell anyone either. I will teach you how to give high quality blowjobs and you can practice deepthroating any time you want and not be judged one bit if you puke. This can be a onetime thing, or if you want you can return for more until you feel comfortable." Jonathan explained.
"I am not looking for a relationship or to steal you away from your fiancée. I just want to offer you my knowledge and experience to help you in your relationship with Tom, which ultimately he will reap the benefits when he returns home to his fiancée that will now give expert level blowjobs." Jonathan continued.
He paused and looked at her hoping to get some sort acknowledgement of his offer, and hoping it was not resulting of him being thrown out of the house. He could see she was contemplating what he had just offered, but it seemed painstakingly long.
"Ok. But you don't tell ANYBODY...ever?" Vanessa asked.
"Not a soul." Jonathan confirmed.
"And nothing more than blowjobs?" Vanessa questioned.
"Not unless you make the request for something else." Jonathan retorted.
"and no cum in the mouth or on my face or body either." Vanessa demanded.
"Fine...not a problem."
"Ok...so how do you want to do this? How should we start?" Vanessa asked.
