Todd's Dream Date

When I left home for the Navy at 18, I could care less about the situation at home. Don't get me wrong, I love my family, every member, from my Mom and dad, to my older sister and my adopted little sister. But when I graduated from High School, my dad announced that he was moving out and divorcing my mom, saying that now that his children were adults and could fend for themselves, there was no reason to keep up with his sham marriage. That was harsh. My little sister, who my family had adopted when I was still in diapers, was graduating with me, jumped one year, so we both were leaving. I guess that's why dad decided it was time to leave, even though technically one of his kids was still 17.

The divorce had not been pretty. All kinds of things came out, things that should have been kept in the dark. For example, it turned out that Allison, my little sister, was actually my mom's kid all along, but with a different man. When Allison's real father, Mister Delaney from next door, refused to accept her, my dad had done the noble thing and taken her in. But then, it turned out that my dad always held that over my mom's head and used it as his get out of jail free card whenever he cheated. In the end, I found out that my dad had won his case to never have to pay alimony, even if my mom had dropped out of school to support his college years and had never held a job because she had been a full time mom. That was a bit rough, but with all the fighting all around, and everyone expecting me to defend them, I had to get out of there.

The Navy, it turned out, was my best option. I was stationed on the USS Boxer, based out of San Diego. My family lives in the Midwest, so I knew I would never run into them. And I never did. Whenever we were at shore, I maintained a small apartment and I never ran into anyone I knew. I was able to start my life over, completely and effectively.

Three years after I joined the Navy, some of the guys got me involved in online dating sites. It worked out a little bit, I found a large number of women who wanted to sleep with a navy guy. I mean, I was a pretty fit guy in general, so I had that going for me, and once I said, "US Navy," well then there were a whole lot of one night stand requests in which I wore my uniform.

Eventually, these sites led me to webcams and initially I wasn't interested. Why would I, I was banging girls all the time. But once you've banged most of the bangeable girls on a dating site, at least all the ones paying attention to you, you start to explore. And explore I did. I made a few friendships with models, joked around with them, threw my money at them, and basically had a good time. It worked out when I was out on some deployment, 'cause I could just jump into their room or private chat with them and it was all well.

That's how things started with my mom. Let me first explain how I came across her. I was online waiting for one of the regular girls, a young redhead, and I was getting bored, so I decided to bounce around. I came across a model calling herself OhioMom, and I thought she looked familiar. You have to understand that I hadn't been home in three years, so I didn't know that after the divorce, my mom lost about fifty pounds and got a boob job to attract men. Actually, it was to attract men online. The only job she had been able to get was doing the webcam thing and apparently it was paying well. Well enough for her to get a boob job, which apparently gets a model more money in the long run.

So I clicked on it and entered the room. The model was turned away from the camera, shoving a long pink dildo inside of her pussy and making all the wonderful noises a woman can make in those situations. I noticed other people dropped tips and to be polite, I did too. I watched for about 5 minutes until OhioMom reached the climax of her orgasm and collapsed into her bed, the liquid gush soaking into her blankets. I was pulled myself out and was stroking at this point, but I wasn't finished yet. I figured I'd keep watching this woman and them probably ask for a private link so that I could request things.

When she turned around and looked into the camera, I got the deep pang sense that I knew this woman. She looked extremely familiar and I just couldn't place it. I kept stroking myself while I listened to her thank her audience, thank her tippers and do all the motions I'd seen several times. The more I watched, the more she seemed familiar.

I decided to send her a private message and she was kind enough to reply. I asked her basic stuff, like if she had videos, how often she was online, etc. But then I asked her where she lived in Ohio. I told her that I grew up in Ohio and thought it was cool that she was from there. She told me that she lived in McClure. You have to understand, the town of McClure is very small, less than a thousand people, so when she said McClure, the wheels began turning. I lied and told her I was from Cleveland, since most everyone else is, and that was the end of that.

The next day, I called my little sister, much to her joy and surprise. We ended up talking for several hours and I found out that she had missed me more than I could have imagined. She told me that she had tried living with mom for a little while, but when she lost all the weight and starting trying to date, despite having money, it was not a very fun situation to be in, so she'd moved in with our older sister. The two of them were working at the local burger place, even though they both wanted to leave, and she congratulated me on getting out. It was a good conversation and I sent her my email so that she could contact me when I was out.

I kept up my online relationship with OhioMom, watching her do all kinds of things for all kinds of people. Eventually, I got brave and started having my own private sessions, never linking cam to cam with her. I shot my load in all kinds of situations, some of them so disturbing that I would never admit to them even if you'd asked me to. But it was fun, and I could tell that OhioMom was liking me too. Besides, I tipped very well each time.

Of course, Allison had sent me an updated photo of everyone and I now knew that OhioMom was, in fact, my mother. That made all the depraved sexual things I was making her do on camera for me even hotter. One day, I took her into private and just chatted. No sex, just chat. I paid her for the time and gave her about $50 to thank her. I had been as vague as possible, but she told me all about the divorce, her children, the boyfriends she'd had since the divorce, and she mentioned a serious regret for losing contact with her son.

The next day, I was about to call her and reconnect, but I saw that she was being invited to travel with some of the other models to SF for a week in which each girl was going to bring 1 guest for a private alone night there and maybe a group sex if the person (s) involved reached a combined goal of tips that paid for the whole trip. The key was that they were going to bring their highest tipper at the end of the month. Forming a plan, I took advantage of the situation.

I began tipping like crazy. Seriously, I made some many tips so often than anytime anyone tipped her, I tipped them slightly more. I was tipping all the time and eventually, I climbed to the top of the Highest Tippers and then surpassed everyone so far that no one was even willing to try to keep up. When I won my date with OhioMom, I was not surprised, although I did not manage to get the group sex, which was a bummer.

My mom contacted me via email and gave me the details of the trip and informed me that I would have to get my own airfare. I told her that I was working in SF, though I was actually in San Diego, but they are close enough, and that's why I had been so motivated to win and she appeared to be impressed with that. We set up our private date and decided that if it went well, we might spend a few nights together with her coming to my place.

The day after that, I got a call from my mom. Allison had given her the number and we talked for a long time on the phone. It was like old times, hearing my mom's voice, and I remembered how much I loved her. I also felt pangs of longing to see her again, missing her and home. There was a creeping, nagging feeling in my head that I should admit that it was me she was meeting in SF, but somehow I managed to keep that locked away. I must have been channeling Oedipus because I let it go unsaid. However, I agreed to meet my Mom, telling her I was stationed in San Diego (she had no idea where that was and offered to pay my travel expenses), when she came to the Bay Area. I told her it was an hour and a half flight and agreed to meet her the day after our previously arranged date, claiming that I had urgent business until then.

A couple weeks passed and I tried to maintain my online contact, but I was nervous and afraid that I would mess something up and blow it. So, I maintained a minimal access, not agreeing to any kind of private conversations, claiming I wanted to save it for our date. I bought a cheap prepaid phone so that she could text me and get a hold of me if necessary. On the day her flight left, she texted me that she was on her way and hoped I was ready for the best night of my life.

My one hour and 30 minute flight to San Francisco turned into the longest flight I'd ever been on. We actually landed a little early, but for me, it stretched on for hours, pulling me into an anxiety that I had to borrow some medication to prevent. When I landed, I would be meeting up with my Mom to fuck her. That was my plan. And if she recognized me, which I was sure that she would, I would play it off like I managed to arrange my business and get there a day early, playing it off entirely.

My taxi ride to the hotel was equally as bad as the plane, but I felt the anxiety medication finally kicking in, and by the time I picked up the rental car outside the hotel and drove to the rented villa the camgirls were at, I was feeling pretty relaxed. The edge was gone, but the excitement was still there. I was forced to cradle a hard cock for the whole drive there.

When I arrived, I found that all the cars parked outside were rented, and many of them were economy class vehicles like mine, which made me feel better. This trip hadn't broke my bank, but it gouged me, that's for sure. I figured, though, it would be worth it if things went according to plan. I mean, I had become quite fond of my mom's naked body and had, more than once, imagined filling her cunt, the vagina that I had been born through, with my cum.

I rang the door bell and was greeted by one of the hottest girls I had ever seen before. I was vaguely aware that her name was Crystal or something of that nature, and I was introduced to her special date, David. He was an older businessman, dressed for a casual day out, but he shook my hand with the grip of someone who did that for a living. I was given a beer and shown out to the back patio where the other girls were swimming naked. It was like something from a 70's porn film, with everyone frolicking around and having a good time.

I stepped outside to see my mom, sunbathing naked near the pool, a glass of iced tea next to her. She always preferred ice tea and I smiled. I walked up to her slowly, feeling all the emotions, first the happiness and excitement of a prodigal son, then the emotions and excitement of sex, each competing for dominance in my chest, but each equally driving my heart rate up, destroying the effects of the pills. I imagined that if I hadn't taken the pills, I probably would have had a heart attack.

My mom pulled her sunglasses down and looked at me for a long moment and I felt for sure she recognized me. She turned her head to the side once and then pulled her sun glasses off entirely. She was gorgeous, more beautiful than I remembered her, but then I remember her 50 pounds heavier. She also didn't have huge tits when I last saw her and usually kept her face hidden behind her hair, but now she had died it an auburn, pulled it out of her face, and looked on the world proudly, knowing that everyone else was appreciating her.

"ArmoredCock?" she asked slowly.

"Yes Ma'am," I returned, pulling in my Midwest politeness.

She smiled and stood up, crossing the distance between us quickly and giving me a hug. It wasn't the tight, long hug of a mother seeing her child again, it was a soft, almost barely touching hug that lasted maybe a little longer than first hugs usually do, but she broke off. She kissed me gently on the lips, this time making it a long affair, before pulling away and looking at me.

"I was afraid you weren't going to make it," she said, "You're the last one to arrive."

"Sorry, Ma'am," I replied. "Lot's of work at the office."

"That's alright," she said, "you're here now." She led me to the chair next hers and offered me some tea. She told me that it was homemade and I couldn't refuse. I had never been able to refuse my mom's tea, it being the best in Ohio.

"That's good tea, Ma'am," I said. "Reminds me of home."

"It should," she said, "I brought everything with me in my luggage. Couldn't trust anything out her in Hippyland. And stop calling me, Ma'am. I'm already extremely nervous to be fucking a guy as young as my kids, no reason to make it worse."

I laughed nervously and drank some more of the tea. I noticed the bottle of anti-anxiety pills on the ground next to her chair and realized that she had done the same thing I had. And then I realized that I had gained about 30 pounds of muscle, shaved my shaggy hair, removed the wispy teenage beard, grown about 3 inches, and had gotten some reconstructive surgery on my jaw when I had taken a door in the face while rushing during my first battle exercise. My mom probably didn't recognize me, at least I looked different enough that the pills and maybe some alcohol, combined with a heavy dose of nerves, probably made it so that even if she did recognize me a little, she would have blown it off as a mistake of the situation.

Especially if she was nervous to be with a man the same age as her son. Chances were that she did recognize me in that first moment but told herself that she was imagining the similarities because she was nervous about comparing me to her son. She probably wrote them off as illusions that he might was playing on her. It occurred to me right then that I would be able to do whatever I wanted to my mom and she would let it happen, never suspecting that I was actually her son.

I looked at her then, appreciating her as a woman rather than a naked version of my mom. I felt my tension roll away and placed in her in my mind in the category of beautiful women I had been given the pleasure to enjoy. While she was in her late fifties, my mom had a grace and elegance that was hard to possess for a woman half her age and also had no signs of bad aging. Call it genes or call it a life of the proper amounts of wholesome, homegrown food, but she was definitely attractive. If I didn't know her exact age, down to the birthday, I would have guessed that she was actually more in early 40s. She had clearly been working out, since she had a well defined body, even if she had looser skin in parts due to age. But still, her pussy was beautifully pink, her tits were round and wonderful, she was a pretty woman anyway, and I realized that I would be a seriously lucky guy to get to enjoy her body under mine. I would consider the motherly aspect later, maybe right when I shoot my load all over her face or something.

We talked about the sunshine and the heat of California, she asked me about my work and I made up stories based on real administrative activities on our ship but placed them in an office in San Francisco, and made up a couple of situations that could only have taken place in San Francisco. The conversation s took up a good amount of time, obviously time to relax and get used to each other, before it was announced that a local fine dining establishment had brought dinner and wine, and that the ladies were going to get into their dresses so that we could have an elegant dinner together.

I share conversation with the other guys while I waited, not really listening to what they were saying. When David privately took a viagra pill, I saw it and pulled him aside. We had a long conversation about how young people shouldn't take viagra when they're young as it might cause problems later. I assured him that this was my first time considering it and that I was only considering it because I wanted to enjoy everyone moment I paid for. He could respect that and gave me a pill, which I drank immediately.

When the ladies came back in, they were stunning. It was hard to point out which of them looked the best, for they all had their high points, but when my mom sat next to me, I could tell she had taken another anxiety pill. She was smiling a bit awkwardly and kissed me on the mouth again, this time probing me with her tongue. I accepted it and the kiss, feeling the warmth of her body against mine. I grabbed her head and gently pulled her into me for a deeper kiss.

I don't know how long we were doing that, but by the time we finished, someone had poured up both a glass of red wine and had placed the first of four courses in front of us. I sipped my glass for the rest of the evening, but my mom downed the first one like it was nothing, clearly still nervous, and took her time with the next one. No one seemed to notice, since everyone was in varying states of anxiety and excitement. A great conversation about sex toys and the comparison to their real life counterparts started and the tension eased, many of the guys in the room relaxing with laughter.

Before long, the dinner was over and we all parted to go on our separate "dates." My mom and I entered her room, which was a fairly large portion of the villa. It was big enough to have a lot of room around the large California king bed and the oversize dresser and vanity across from it. There was a large bathroom with a shower and you could lay on the bed and look in to watch the person showering if you wanted.

My mom told me to lay down and she went into the shower, cleaning herself off. I smiled and leaned over, watching her from bed until the steam blocked my vision. Feeling the nervousness creep in again, I walked over to the large widow and looked out, seeing a view of buildings and lights. It wasn't the greatest scenery, but it was to be expected in an urban setting like that.

"Nervous?" I heard from behind me. I turned slowly to see my mom wrapped in a white towel, the cleavage from her large breasts very evident and her auburn hair pulled back from her face. I could see her age now and still found her extremely attractive.

"Yes," I admitted. She smiled and walked over to me. I felt her come close and thought she was coming in for a kiss, but she stopped short. A moment later, I felt her hand sliding up the length of my khakis and coming to rest on my cock. I felt the blood flow in quickly and quietly thanked David and his viagra.

She smiled and led me over to the bed, lying me down. She climbed on top of me, straddling me and looking down. I could feel the weight of her on my pelvis and it made my erection grow harder. I looked up at her and smiled, seeing then, when I was looking just into her face, my mom and not the different woman I had been imagining she was.

"I have a surprise," my mom said. She reached down and took my hands in hers, placing them on to her hips. I held her there while she leaned over and pulled a black bag from under the bed and set it down next to us. She opened it to reveal a Sony camcorder. She pulled out the camera and held it in both hands, showing me the HDR-CX900 on the side. I had no idea what that meant, but I got the feeling that it was an HD Camcorder.