How Annette Turned Me

Over the years I've dated a lot of women. One of the things I've found interesting about them is the many secrets they have. Some share them, some don't. It is just a matter of getting them to come out of their shell.

This rings most true in the bedroom. When you take a woman to bed, you really don't know who you are taking the first time. Even then, you really don't know who you are in bed with. The sluttiest of women can be rather reserved in the bedroom and the most straight-laced women can turn into sluts. In my 20s, I prided myself on the fact that women would say to me, "I've never done that before."

I've been burned, of course. I dated a woman for a long time and she was amazing in bed. Blow jobs at the drop of a hat, anal sex, we acted out porn movies, etc. Later on, I discovered she had many personal issues and suddenly a blow job was sexual abuse. There is nothing worse than being with a woman who used to go down on you in a second to feeling like you are a sex fiend if you want one.

As I said, for the most part, I could peel their layers and open them up to the things I enjoyed. The one exception I had in my 20s was one Annette Bishop. I was in the army and traveled around quite a bit. For about 3 years I was stationed at Fort Leonard Wood in Missouri and made my way through the bars. A few years older than me, Annette could have easily been in the army. Yeah, there were all types of women in the army, but she fit the profile of the army wanted in a female: very slender, breast cup size A or B, short black hair and arms that looked like she could keep pace with the boys on the army PT test. Don't get me wrong, she was very attractive, and when she dressed up, she looked like a knockout. At the same time, though, she also looked like she could handle a 26 mile road march and not think anything of it. I guess the way I could describe her is an attractive version of Demi Moore in the movie G.I. Jane (but with hair) - which is fitting because it came out around the time I first got stationed there (late 90s).

While I met a lot of ladies in bars, I met Annette at the gym. I hated working out at the gym on the base and honestly didn't pay much attention to the ladies there. I would get in my zone and wouldn't notice them. Yeah, when I was done with my workout I would see the ladies in the tight shorts, etc., but I didn't notice Annette, she noticed me. It wasn't like we hit it off right away, though we did poke fun at each other and even got into a competition on the stationary bikes. What I really liked about her is that she would sweat just enough that when she began to cool down, her nipples would poke through her tank top like pencil erasures. I had been working out there in the summer of 2001 and eventually I figured out her schedule. After weeks of timing my work out to be at the gym the same time as her, I finally got up the nerve to ask her out.

We went out a couple of times before we had sex the first time and bluntly put, it was rather vanilla. I am not saying she sucked at it, only that she didn't make a lot of noise and outside of the warm-up BJ, it was pretty normal stuff. In fact, I was worried that she didn't enjoy herself at all and had doubts that she would want to go out with me again. I stayed the night, but I had to be at morning formation at 5 am the next day, so I didn't wake her when I left. I did leave a note and was happy when she texted me asking if I was going to be at the gym that day.

At the gym she asked if we were going out again and didn't say anything negative about the sex. In reality, it was killing me. I always felt good about my ability to please a woman and for the first time, I felt like I hadn't. A few nights later we went out and I was happy that she invited me back to her place again (I lived on base and it wasn't much of a place). I was bound and determined to make her feel like I was the best lover ever and spent a lot of time going down on her. The sex was passionate, but I still felt I let her down. As time went on we had sex a few more times, but never had those fireworks. Worst of all, I was not in the typical position of getting her to explore my kinks. Usually by the 3rd or 4th time in bed, the ladies I would be dating would start talking about things I enjoyed and more often than not, the women would try to follow through to make me happy. In her case, none of this happened. Oh, she was good to me, great at giving head and things, but I tried different avenues to really get her off without much success.

One day, I had a little alcohol and shared my fears with her. I guess she had a little more alcohol than usual, too, because she opened up as well - started playfully saying that she needed another man to show me how to do things. We even talked about her making me watch her get fucked and as we had sex scenario-playing like that, the sex got hotter and hotter.

Some of the times it would involve her masturbating with a large dildo while I would tell her how hot it was watching her get fucked. Sometimes she would make me masturbate myself and sometimes she would have me get on her and take "sloppy seconds." As time went on, the scenario set up would get more and more detailed. One time she tied me in a chair and made me watch as she used one dildo on her pussy and slid a smaller one in her ass. She talked about making me watch her service two guys. The saving grace of that situation was that when she was done, she came over and gave me a blowjob (while I was still tied up). She talked dirty through the whole thing and said things like, "I want your load so I can have cum in all three holes." She swallowed it down with a smile and it was by far the best blowjob I ever had. As she untied me, she winked at me and said, "We need to make it happen."

During the next few weeks, it got dirtier still and I was willing to do whatever it took to make her happy. So long as she was happy, I had incredible orgasms. There was never a night of plain sex or lovemaking. It always involved talk about bringing others into the bedroom. Then one day I texted her and asked, "What would you like me to do for you tonight?"

She texted back, "Bring a friend with you and make sure he is hung."

I laughed it off, but showed a buddy of mine who was intrigued by her dirty talk. I showed up at her place that night and she was dressed in a corset, thigh highs and had her makeup done up. I had wood the second she answered the door, but a few moments later, I could see she was upset. She playfully asked, "No friend?" and I laughingly apologized. She followed up with, "Well, I will make due, but you will be punished."

I wasn't sure if she was serious or not, but when we got to the bedroom she tied me up again. She pulled out the two dildos and played with herself, talking about as nasty as ever. She looked so hot in the outfit that I almost came without being able to touch myself. I was so happy when she was done and came over to me. Instead of the blowjob, however, she only freed up one hand and arm. She stood in front of me seductively and said, "You didn't give me what I want so now you don't get what you want. Take care of yourself, but don't make a mess." While I did this, she belittled me and said things like, "you think I would let you stick that little thing in me after not giving me what I want? You need to bring a MAN over to really make me cum." I eventually came (she DID look hot in that outfit). When I was done, she untied me and told me to get out.

What got into her? Roleplay was one thing, but did she really want me to bring a guy home to fuck her? Was I really that bad in bed?

I didn't call her after that, but one day when I left the base, she followed me to a bar. She sat down next to me and asked why I hadn't called her. When I gave her the reason, she frowned. "I guess I thought you were different," she said. "I thought you wanted to please me. I guess that isn't the case. The sex could have been really good, but apparently not with you. I thought we were doing a good job of pleasing each other, but I was wrong."

"Of course I want to please you," I begged, letting my other head do the talking. "If that is what you really want, I will make it happen. If you want to fuck me and another guy, I'll find someone."

"Did I say that?" she replied. "No, I want you to WATCH me fuck another man."

"What, do you want me to find some guy on line or something?

"On line? No," she continued. "I don't want some stranger from a chat room. I want you to bring me a guy from the army. I want you to watch me fuck one of your friends. Besides, I don't do rubbers and you guys get constantly checked out. Don't worry," she followed as she stroked my cock through my jeans, "I will make it worth your while." With that, she kissed me on the lips and walked out.

I sat at the bar milking my beer. "What the hell?" I thought. I liked this woman, I really did, but something about this wasn't sitting well. In a way I had fallen for her. Not in an "I want to get married" sort of way, but in a way that said, "I need to keep her in my life and I need to keep her happy." Was this the way some women felt about me? Was that why they did what they did?

I knew the friend I would get. It was the one I showed the text to. He wasn't a best friend, but he also wasn't one who would brag about the situation, either. He was kind of quiet about what he did with his lady friends and he had a few of them. Some guys bragged but didn't succeed. This guy succeeded but didn't brag. I had just got up the nerve to talk to him after afternoon formation when I got the text from Annette. It said, "It needs to happen tonight. Eight o'clock sharp."

I grabbed Bill after formation. He was a squad leader from another platoon, but since I was a platoon sergeant, he knew me well enough. He could tell I wanted a private conversation so we walked away.

"What's up, Jon?" he asked.

"You remember that text I showed you from a few weeks ago? The one where the woman I am seeing told me to bring a friend?"

"Yeah," responded Bill. "Are you still seeing her?" Bill had just grabbed a diet coke from the machine.

"I am, though..." I trailed off. "I am not sure quite how I feel about this woman. The sex is GREAT, but she is different than any woman I have seen. Thing is, she was serious about that text."

"Sppooooot." Bill spit out his big sip of the Diet coke and I think some had gotten up his nose. When he caught his breath he asked, "Are you going to do it?"

"Well, that is kind of why I am talking to you. Would you be interested??"

"In a three way?" Bills voice carried a little but he silenced down and followed with, "Are you asking me to do a three way with this chick?"

"Well, not really," I said kind of fading out again. "Thing is, she wants me to watch."

"Woah! I am not really into that," Bill said putting his hands up. "To be honest, I have never actually done anything like that in front of someone. Yeah, I had a three way with two chicks once, but I never felt I was on stage. To be honest, I would be worried about getting it up."

"I understand if you aren't interested," I replied encouragingly. "I am not sure if I would be. This is all new to me. As for getting it up, if any woman can get you up, she can. Stage or no stage. Don't' worry about it, I will try to find someone else."

"Hold the phone," Bill interrupted before I could leave. I'll do it. To be honest, I have been in a little bit of a cold spell since Julie and I parted. I could use something that isn't my hand. Are you cool with this? I mean...well...you know?"

"I won't say it isn't awkward. It is. That is why it has taken so long. Can you meet me at 1930? She wants to do this tonight."

"TONIGHT!! Thanks for the notice, bro." Bill was only half joking. "OK, I'll see you at 1930."

We met up at the NCO club and each had a shot of whiskey. We were both nervous, but for different reasons. I didn't know how I would act and Bill didn't know what was going to happen. The drive there was pretty quiet, but he did ask for any ground rules.

"Two," I said. "First is no condoms...I'm sure that won't bother you. The other is that if I give you the cue to go, please do so - no matter what transpires beforehand."

I knocked on the door and was again greeted by Annette wearing thigh highs, heels and a corset. She looked even hotter. Her face lit up at the site of Bill and she greeted me with a kiss. I introduced them and she greeted Bill with an even bigger kiss. By what I could tell, Bill no longer had the erection concern.

Annette guided us to her bedroom; her ass looked sexier than ever. When we got to the room, she had a recliner there and there was no sign of handcuffs or things to tie me down with. She told me to sit and watch and proceeded to lean into Bill. There wasn't much conversation and I don't think Bill minded. He was clearly horny at the sight of her and once they started kissing he got even more excited. Bill wasn't assertive at all, waiting for Annette to make all of the moves. Slowly but surely she started to unbutton his shirt and undo his pants. While I wasn't jealous of the kissing so much, at this point I started to stir.

When she heard the creaking of the chair, Annette looked over at me and said, "Please feel free to move the chair so you have a better view. Maybe you can learn something." My face turned beat red, but Bill never let on - he was too caught up in the seduction.

When she undid his pants it became clear that Bill was going combat. His cock sprang out at her, smacking her in the face. "Whoa," she said, grabbing a hold of his cock. "This large of a tool won't need any teaching." She was right. Bill was clearly an inch thicker in diameter and a couple inches longer. I wasn't small, but Bill didn't have a normal sized cock. She helped Bill out of his pants and then proceeded to lick his shaft. Bill was more than appreciative when she started to give him head, and got down on her knees to do the task. Like with her first time with me, she was deep-throating him - taking every inch of his cock in. Unlike the first time with me, she was gagging in the process, while at the same time she seemed to be getting into it more.

She played with her pussy a bit and took her mouth off of his cock while still stroking it with her other hand. With this, she looked up at Bill and said, "I need to get my pussy ready for a cock this big," and went back to sucking it while playing with herself with her free hand. I could tell that Bill wanted to cum, but he also clearly wanted to fuck her. Annette was reaching around and grabbing his ass with her stroking hand and pulling him in, but then she stood up and said, "I think my pussy is ready for you now. Would you like to fuck my little pussy? Would you like to show Jon how to fuck a woman like a real man?"

Bill didn't need any more encouraging. He climbed on top of her and she spread her legs and wrapped them around him. He buried himself in her with one slow steady thrust. Annette gave a little squeal of delight as he did this and said, "I love having a big cock in me." Bill began a rather rhythmic motion and with each thrust he got a similar squeal - a noise I had never heard her make. To top it off, Annette started to say things like, "put your cum deep in my pussy" and "give me that sticky load and make me yours."

I am not sure if it was the dirty talk or the sounds Annette started to make when she climaxed, but something sent Bill right over the top and he thrust several deep thrusts before finally resting with his cock fully in her. Annette kissed Bill full on the lips and it almost appeared that she was trying to keep his cock in her while it went flaccid. Eventually, though, he got up and when I gave him the motion to dismiss him, he quietly dressed and left the room.

Annette lay their quietly, but with a vivid glow on her face. She smiled over at me with her freshly-fucked face and said, "You did a very good job picking him out. Now come over her and fuck me. Stick your dick in my sloppy pussy."

Though slightly disturbed and humiliated, I also had a raging boner from watching Annette get fucked like that. I came over to her and saw that Bill was leaking out of her a tad. I put it out of my mind and slid my cock right in her. Her cunt was as loose and as wet as I had ever felt. She groaned a little from having the new cock in her, but not like she groaned with Bill. The dirty talk picked up right from our play with the vibrators. "That's it, push Bills cum deep in to my stretched out pussy. Show me how it pleases you to watch me get fucked like that. "

I have to admit that between the dirty talk and the kink of the situation, I was really getting into it. Lingerie, porn, etc are great for turning a guy on, but there is nothing that turned me on more than watching her face as she was cumming. I can't say it was a better orgasm than Bill gave her, but it was better than she had with me. As she laid there begging me to pound her deeper, I thought about depositing another load where Bill had just put one moments earlier. As I came, I kept thrusting, even after I was done. I wanted her to know who she was fucking and I wanted to make a mess of her pussy. At last I pulled out and flopped on her bed, but she hopped up and started sucking my cock right away. It seemed she was relishing in tasting our cum on my dick. Normally it took maybe 30 minutes before I would be ready to cum again, but the way she was worshiping my cock sprang me to life again, soon.

Annette proceeded to give me the sloppiest blowjob I ever head. She licked me all over, sucked my balls and literally drained me of every ounce of cum I had left in me. She continued to suck on my dick even after I came, but my penis was so sensitive at that point I had to get her to stop. She smiled, came up, put her head on my chest and wrapped her arms around me. I fell asleep about as content as I had ever been with Annette.

I had early formation the next morning, and I headed off to the base with Annette still sleeping contently. It was a long day for me and it wasn't until the end of the day that I got a text from Annette saying, "Thank you for an incredible night last night. Meet me at the gym on Friday at our regular time and I will give you a treat."

To Bill's credit, he didn't say anything to me, but waited for me to bring up the subject. Some guys would have run around the base talking about banging another guy's woman, not Bill. He was quieter. When we did talk he basically told me that he was starting a new relationship with a girl and if it went well over the weekend, he wouldn't do a repeat. He liked her and he was more of a "one woman at a time sort of guy." I respected that because I was, too. At this stage in my life, I was deeply into Annette and was willing to do whatever she wanted for me to please her.

When I got to the gym on Friday, it was practically empty. I was having a good workout even before Annette arrived. When she did, she was wearing some sort of spandex pants. Yoga pants are the style today, back then it was more spandex or something. She was also wearing a cut-off shirt, so when she was sweating on the treadmill, I could see beams of sweat forming and rolling down the small of her back. She asked, "Do you like how my ass looks in this outfit?"

I gave a quick acknowledgement of "Hell yeah!"

A little softer she said, "I am headed home right now. When I get home I want you to show me how much you like my ass. I want you to clean me with your tongue and then fuck my ass."

I stopped pedaling right away and headed right for the car. Though she had put a small vibrator in her ass before, we had never done anal sex. In fact, it had been well over a year since I had fucked a woman's ass.

It was a short drive from the gym to her place, yet we raced home faster than the characters in Basic Instinct. When we got to her bedroom, she still had sweat gleaming on her and she removed her shirt so that she was only in a sports bra and the spandex pants. She turned with her back towards me and instructed me to clean her up. I pulled down her pants slightly and kissed the small of her back. She bent over and I started to slide my tongue down her crack. At this point the pants were around her knees and she was bent forward, with her hands supporting her on the bed. I squatted down and removed her pants and she kneeled on the bed in front of me. I came in behind her and resumed my activities in her crack. Finally I slid my tongue into her butthole and she shuddered a little. I grabbed her by the hips and started to bury my tongue in her asshole. She grabbed me by the back of the head and forced me in as far as she could. The aroma was fairly sweet, despite where I was licking. She took her hand off of my head and started to rub her clit a little. It was here that the dirty talk started.