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After The Train

Part 3, Chapter 6: The Next Weekend In Chicago That Wasn't - Abby Surrenders Her Virginity

At the time, I didn't know the vocabulary to use to "classify" Catie. I think in today's vernacular she might be described as a switch. But I'm not really sure. Sometimes she was a Domme. Sometimes submissive. We all probably have a bit of both to get what we want and to give to another what they want or need. But I was often surprised by her and what she wanted and what she was willing to do to get it.

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"Is this what you and Abby have been planning?" I asked. She shook her head yes. After a short pause, I followed with next question.

"Abby has decided this is what she wants to do? Or is it something that you want her to do?" I'm sure it sounded as accusatory as it looks written down.

"She seems pretty certain," Catie said.

"Well, this is a really big choice. She can't get her virginity back. Have you told her that?" I asked.

"Not directly," Catie said.

"I think it's a decision that I ought to have some say about, too, don't you?"

Catie was surprised by my saying this. She assumed that I would leap at the chance to "deflower" a virgin.

"There are things we should discuss before any of us go down this road including things like whether she really wants to do this now and with me. There's also birth control and just what the two of you expect from me."

"I expect that you'll be your wonderful self and I have no doubt that you'll give her and me the time of our lives."

"And you're okay with this?"

"Yes."

"Why?"

"Why, what?"

"Why are you okay with it and why now?"

"She likes you, she likes what she's seen with us, she likes the way you made her feel. She wants more of that. She wants to feel what it's like with someone who knows what he's doing."

"She wants what I have."

No five words that Catie ever said to me were ever so prophetic, though I didn't imagine the way that might turn out in that moment. I certainly was thinking about the intensity of the excitement in sexual discovery and awakening, particularly when experienced for the first time. It didn't occur to me that it might become a matter of being a possessive tug of war between two sisters.

"If you don't mind, I'd like to talk with her about it before things go too much farther."

"If you have to," Catie said. I could tell she was a bit put out by my reluctance.

"Yes, I have to. I have to hear it from her rather than just assuming it's okay," I said.

We laid there quietly for a few minutes cuddled next to each other. My marriage had come undone, in part, by having a third person involved in my closest relationship. Here I was, now, in the process of sharing or being shared in a new close relationship. I was (and still am after all these years) struck by the irony of the situation.

Finally, I broke the silence with a question; "How are we going to hang the bags?"

The rest of the morning was uneventful. Catie and I ate breakfast with Marianne. Catie and I went over to the hospital and we sat with her dad. The TV was on in his room, the doctor came by to give an update to Catie, and the nurses came and went for periodic checks and whatever else they needed to do. I would describe Catie's dad as being "in and out." Neither of us were very hungry at lunchtime, so we skipped going to lunch at the hospital.

Marianne arrived at the hospital a little after 2 PM. Shortly after that, the doctor came by again. After the latest update from him, Catie and I prepared to leave.

"Are you headed home?" Marianne asked.

"No, we are heading over to REI to see if there's something I just can't live without before I head back to North Carolina." At the time, there wasn't an REI near me. I had been to their Seattle store and the Portland (Jantzen Beach) store, but those were the only two I had visited at the time. They were expanding the number of stores and during those days, visiting new stores was something of a bucket list thing to do. But the thing about buying clothing and related gear in Oregon was no sales tax.

We left the hospital and I did buy some stuff at REI to take back to NC. It was mostly related to climbing and not so much skiing. I know Catie was anxious to get back to the house and my shopping made the anticipation of what was to come (or cum) all the more tantalizing.

When we arrived, Abby was not there (yet). She was planning on leaving the high school and going directly to the hospital. I asked Catie what she wanted me to do. She directed me to retrieve an unused coat/hat tree from one of the downstairs rooms and bring it up to the bedroom I was in. I saw that Catie had retrieved another coat tree when I brought it in the room. She was already hanging her enema bag on one of the hooks. I placed the rack I brought upstairs on the other side of the bed. Catie had me get my enema bag out of my suitcase and hang it up (empty).

"And now we wait."

It was just before 4 PM when Abby arrived home. We were sitting in the living room when we heard her car pull into the driveway. Catie and I had been trying to talk through the alternatives she and Abby had discussed the night before and early in the morning. But without Abby, it was difficult to know what was really going to happen. I looked out the window and saw there was a second car that pulled in behind Abby's car. I told Catie that there was somebody else outside. Catie looked out and told me it was one of Abby's friends (her name was Stephanie).

"This just keeps getting better and better" I remember thinking, somewhat sarcastically.

They came into the house and Abby introduced Stephanie to me (Catie already knew Stephanie). My instincts told me that Abby and Stephanie had talked about what had happened (so far, and what might happen?). My instincts also told me that she was one of Abby's sexually active friends. It was just the vibe I was getting from her and the whole situation like she was sizing me up. But not quite "Hi! I'm Stephanie Big Tit, you wanna fuck?" But I also told myself that I could just be imagining it all, that this was another high school senior, and to keep it all civil and pleasant conversation.

"We're going upstairs for a few minutes," Abby said after all the pleasantries were concluded.

We watched them go up the stairs, heard a bedroom door open and close, and heard some music playing from Abby's bedroom. We could hear muffled conversation and laughter from time to time.

"What's that about? Is this part of the plan?" I asked Catie. She had no idea. But Catie did confirm what I thought, that this was one of Abby's sexually active friends.

We sat downstairs in quiet conversation and anticipation of what was next. About 20 minutes later we heard Abby's bedroom door open, the upstairs bathroom being used, and then finally Stephanie saying goodbye to Abby and coming down the stairs. As she came through the living room she told me that it was nice meeting me and that she hoped that we had a good evening. She was grinning so much that she could hardly get the words out. Then she went out the front door to her car and left.

Catie and I just looked at each other not knowing for sure what that was all about. We didn't have to wait long.

Abby came down the stairs slowly and carefully. She was quite a sight to behold. She was wearing a sheer black negligee and was coming down the stairs in Lucite heeled black shoes. She wasn't wearing much underneath, just a garter belt that held up a pair of black laced-topped hose. She was also "dolled up," wearing more make up than I'd seen her wear so far (mostly around her eyes and lips). Catie had never dressed up for me this way (though she was fond of letting me know when she wasn't wearing underwear).

"WOW Abby!" was about all I could get out as she reached the bottom of the stairs. I certainly didn't expect this. If Catie said anything, I didn't hear it or it didn't register. I thought that Abby was coming down the stairs slowly because of the shoes she was wearing. But when she reached the bottom of the stairs, I could tell she was perceptibly shaking. I asked if she was okay and if she wanted to sit down. She indicated that it was a little cool downstairs and she was nervous as she sat down.

"Well, we all need to talk," I said. Abby asked if we could go back upstairs where it was a little warmer.

"Where?"

"My bedroom," Abby replied.

We agreed. Abby got up and headed up the stairs and I followed. Catie said she'd make sure the doors were locked. It was a wonderful view for me looking through that sheer negligee and the way the the lace-topped hosiery framed her ass. I remember thinking that we needed to get Catie some of this lingerie because it would nicely frame her assets. When we got to the top of the steps, she asked me to go get the enema equipment and bring it into her room. I figured that she knew and had seen that Catie and I had set it up in the bedroom where we had all been together earlier that morning. I went into that bedroom and brought the coat tree's with their empty enema bags into Abby's bedroom.

The lights were on in her room and they were fairly bright making the room warmer than than the hallway. In many ways, Abby's bedroom was a typical teenage girl's bedroom (or at least what I knew about them). Yes, the posters on the wall had changed with the times. When I first saw her room when I arrived on Saturday, she had a collection of stuffed animals and stuffed toys scattered about the room and mostly on her bed. The ones on her bed were all removed and piled up on her desk beyond the foot of her (queen size) bed. There were pillows and a stack of towels on her bed. I put one of the coat trees on the far side of the bed (which she adjusted a bit) and the other to the near side. About that time, Catie arrived in Abby's room.

"So, let's talk. All of us," I said.

Abby sat down on the far side of the bed. Catie moved up to the head of the bed where the pillows were and laid across the bed. I sat down on the near side of the bed to complete the triangle between us. The door to her bedroom was partly open but it was just the three of us in the house.

I started first with "I know you two have been playing around and coming up with some sort of plan for me. And it's very, very exciting (for me) to know that." At the moment it was also very exciting because I was looking directly at Abby, her breasts visible through the sheer fabric and the opening of her negligee.

We got down to the meat of the conversation, so to speak.

On what she wanted to do and why (me): She "wanted to be fucked the way I fucked Catie." Well, that was blunt. She wanted to feel what it feels like to have someone who knows what they are doing explore her inside and out. She wanted to know what it feels like to have me cum inside her and maybe cum together. She liked what she felt when my lips and tongue were at her pussy. She was very specific about what she wanted to do, particularly with vaginal AND anal sex. She wasn't being coy or shy about it.

I told her, and she was aware, that there is a certain fantasy about older men and a young woman. But not all those relationships are healthy ones. Part of the fun is sometimes fumbling along together with someone your own age. I expressed concerns that I was 32 and she was 18. She said I wasn't too old for her, or something like that.

On virginity: I had asked her directly if she was a virgin. From my perspective, she seemed embarrassed to admit to her virginity, but she did. She told me that she had given a guy a blow job once on a dare. I asked her what she thought. She told us he came so fast that she hardly had a chance to take his cock into her mouth and then his semen dripped onto her breasts since she was wearing a scoop neck shirt. Nothing like what she experienced with me in her mouth, at least.

I told her that once she surrendered her virginity, to me or anyone else, she couldn't get it back. I also told her that I wouldn't be offended if she decided that she'd rather wait or wanted to find someone else "to play with." I was trying to give her (and me) an out. I even mentioned my friend who used anal sex to preserve her vaginal virginity for whoever she married and pointed out that was always an option. No, she was really interested in "losing" her virginity to me, particularly with her sister there "to help." What she had seen between Catie and I and what she experienced with the three of us really convinced her that she wanted to do this and I was the one she wanted. She was aware from everything she knew that there might be both blood and some pain and discomfort from being penetrated the first time (both vaginally and anally).

Catie said very little, intent on letting me have the conversation that I hadn't had yet.

On birth control: she was taking birth control pills to control her periods. She had some problems in the previous years after she reached puberty with unpredictable and painful periods. She had been on birth control pills for roughly a year and her periods were predictable and much easier to deal with. Now that she was an adult, she didn't need her parent's permission but it was something that was not controversial for medical reasons.

She told me that she was at the place on her pill pack where she was just about to start her menstrual period. That was another blood concern. Abby asked me if that bothered me.

"No, it's just something to deal with."

As I have always told any partner of mine since I became sexually active, if at any time that she wanted to stop, all she had to do was tell me and I would stop. No anger or guilt trip. I've always felt that way. I asked her if she had any questions. She asked them and I/we answered them.

"So, you've been thinking about this all day?" I asked. She said she had and then went on to describe what her day was like, how wet she was all day, how she had to change her panties, etc. I asked about Stephanie. Yes, she had told Stephanie that she was planning to sleep with me and Stephanie also helped "prepare" her. All of this conversation took less than 20 minutes.

During this last part of the conversation Catie had become restless and wanting to remove her clothing. She asked Abby, more than me, if she was ready.

"I'm ready," she finally said.

With that both Abby and Catie got up off the bed. Catie removed her clothing first and then came to me from the head of the bed. Abby got some pillows from the head of the bed and placed them on near side of the bed in front of me. She laid out some towels on the bed and then came around to me and the two of them undressed me. There wasn't much for me to undress when it came to Abby. I merely had to slip the negligee off of her shoulders. I asked if she wanted to remove her garter belt and hosiery and she said "No, it makes me feel sexy." I assured her that she had no problem when it came to being sexy, with or without the lingerie.

It was obvious how Abby wanted us to lay across the bed and so I took her hand and lead her back around to the other side. I told her that she should be on top so that, as her sister had told her, she could be in control of penetration. I wasn't "concerned" about enemas at that time. I sat down on the bed and pushed myself across the bed to lay my head on the pillows. Catie got on the bed on my right side. Abby crawled onto the bed like she was on the prowl. She was on all fours as she placed herself above me and I took the opportunity take her very erect nipples into my mouth and gently suck one and then the other, back and forth. This excited Abby even more than she already was.

"I'm ready...." Abby exhaled.

She reached down between her legs to position my cock so she could slide down it. Catie told her to take it slow and that as she took me in, try to keep me inside her if she needed to back off because it was too intense. In a moment, I felt the tip of my cock make first contact with the wetness of her labia lips. Between my pre-cum and her wetness, we were probably very well lubricated. We could add some "help" (lubricant) if needed, but we didn't start off that way. The tip and the head of my cock seemed to easily slip in and then beyond that I sensed "tightness." Abby propped herself up with her hands on my shoulders, her arms supporting her.

It took about 47 seconds to lower herself to the point where there seemed to be maximum resistance and then a sudden giving way. I assumed that this was her hymen giving way under her weight. She stopped and held there for a moment. I asked if she was okay and she nodded her head that she was. I heard Catie tell Abby that she's "almost there." It took her another minute to bury me inside her balls deep as she sat straight up on me 1:51 after "first contact."

There was a dialog going on between Abby and Catie, though it was pretty clipped as Abby was adjusting to the sensations of having a cock inside her vagina. With slow and deliberate movements she began to slide up and down me with more vigorous strokes. Her first orgasm with me inside her came at 2:37 after she bottomed out on me. She was very warm, very tight, and very wet. About 10 minutes after she had first started to insert me and as she finished another orgasm, she wanted to roll over and have me on top of her.

We tried to complete the roll without me coming out of her, but we didn't quite have it (practice was needed, obviously). She rearranged herself on the bed so that I could reenter her. But before I did, I went down on her to check out how she was doing (with my lips and tongue, of course). There was a little blood and had that metallic taste in my mouth. But it wasn't much to be concerned with. I did this for a couple of minutes before moving up her body to continue her first intercourse.

Throughout this session Catie continued to give guidance and encouragement, mostly to Abby.

Positioned back between her legs (which she drew up), I brought my cock back into contact and asked if she was ready to continue. She was and I took my time getting back into her. I felt myself getting closer to cumming and at one point she asked me to pull out to take a look at my cock because it was "getting bigger." Catie assured her that it only felt that way as it was only a little increase in size. I slid back into her and continued stroking into her. She had her legs up and her ankles around my shoulders as I was ready to cum. I pressed myself in as deeply as as I could and 27 minutes and 52 seconds after "first contact" I began spurting my cum deep inside her.

As the last contractions dribbled in the semen from my "filled up balls," I released her legs so that she could lay them back on the bed. I was propped up on my elbows over her. I kept myself inside her and asked how she was doing.

"Wonderful," Abby said as she gently stroked my body with her hands. I told her that I was going to try to stay inside her as long as I could. I didn't put my full weight on her but she had me in her arms. I was still pretty hard and didn't really go flaccid very quickly. I could feel myself coming out of the refractory recovery period and very gently started to stroke inside her. This usually proved to keep me harder for a longer period of time.

"Can you fuck me, again?" she asked.

I looked up at Catie, who had been fingering herself throughout the interlude between Abby and I.

"Can I fuck her again?" I asked.

"CAN YOU EVER!" Catie exclaimed.

And so round two between Abby and I began. I got hard again inside her as I began stroking in and out of her. As I did, the combination of my cum and her pussy juices leaked out and ran down her butt crack to form an enlarging wet spot on the towels underneath her. Her second time was a much more vigorous fucking, but I didn't pound her like I could have. She was still tight, but the natural lubrication was working well.

It took me about 23 minutes to cum inside of Abby the second time.

Once again, I stayed inside her after cumming and I would have stayed longer except she told me that she needed to pee. I slowly, and reluctantly, withdrew my cock and it released a flood of semen out of her. I rolled off to her left side towards Catie to let her get up. She took the towel that was under her to the bathroom while holding it between her legs.

"Was it as good for you as it was for me?" I asked Catie.

"It was something to behold," Catie said. She had more to say about it than just that, but she was interrupted by Abby calling for her from the bathroom. Catie left for the bathroom.

A few minutes later. Catie returned to Abby's bedroom.

"Is everything okay?" I asked.

"Everything is fine." Catie said. With that, she took one of the enema bags from one of the coat trees and told me it was enema time and I needed to prepare myself.