Anal Surrogate

I'd enjoyed anal sex with a previous girlfriend named Linda. Neither of us had done it before but after trying it, we both enjoyed it. As it turned out, she enjoyed it a little too much because one night we were at a party and I'd left her talking with some of her girlfriends. When I went looking for her a bit later, a guy was just coming in from the yard and told me if I wanted a shot at a hot piece of ass, I'd better get out there before Jason was done. When I got to the yard, there was Linda, bent over a pool chair in a dark area of the yard, getting her ass fucked by Jason.

Jason was the typical jock, great at football, soccer or pretty much any sport and even more outstanding was the size of his cock. We'd all seen him in the shower after gym and it was at least 7" soft. Now seeing him fucking Linda, I could see he had to be at least 10" hard, thicker than I was and while she was moaning and whimpering, she was taking every inch he could give her and it seemed like he wasn't the first one of the night.

I dumped her about 15 seconds after seeing that and after a couple of short relationships, I'd met Janet and we'd been going out for about 8 months, I was 22 and she'd just turned 20. She was my first 'serious' girlfriend - we both enjoyed sports, walking, biking, camping - pretty much anything outdoors as well as pretty much the same for what music and movies we liked. I thought she was hot...long, dark hair, dark eyes, firm boobs/ass and an awesome smile. Her mom was a definite MILF and looked young enough that she could easily pass for an older sister. Janet had a younger sister named Carol who'd just turned 18, she was really nice but didn't look much like her sister. At best she was an 'A' cup, thinner and unless her jeans were really tight, she didn't look like she had much of a bum at all. One day, Janet showed me some pictures of her from a few years earlier and she looked about the same as Carol did now so I guessed that Carol just hadn't 'bloomed' yet and when she did, she'd likely be just as hot as Janet.

Thankfully my room was in the basement and my parents' bedroom was on the second floor so I'd never had a problem having a girlfriend over for some fun and I even had a couch and a tv so I could sit and play video games or watch a movie. We'd been having sex since about the third date and that was great too...she gave great blowjobs, I loved making her cum with my tongue and we fucked in just about any position we could think of. The only thing I learned very quickly was she wasn't into any sort of anal penetration.

She was fine with a finger brushing over her pucker and didn't seem to mind if my tongue drifted a little too far when I was going down on her but the one time that I tried easing a fingertip into her bum, I got a loud "fuck no" followed by a lecture on anal penetration being nasty and something not done by 'normal' people and if I tried it again we were through.

If that was the only thing she wasn't into, I figured I could live with it so we smoothed things over and carried on. Everything went great until a month or so later. We'd been out at a party, had more than a few drinks and my parents were out so we went back to my place. Soon, she was bent over my bed while I slid in and out of her pussy. As I thrust in, she pushed back and we were both enjoying the feeling of what we were doing. At the same time as I was watching her pussy opening to take my cock on each thrust, I was also watching her asshole pucker and relax with each thrust. Maybe it was the beer, maybe it was just testosterone but either way, I decided to pull out and push the head of my cock against her pucker. Not realizing I'd shifted, she pushed back again and before she could stop, the head of my cock was suddenly in her ass.

She screamed and pulled away, I tried apologizing and blaming it on a 'mis-stroke' but in the end, we argued and after telling me we were through, she left.

I kinda wanted her back but at the same time was thinking maybe I should just wait and see what happened. About a week later, I got a text from Carol that said, "I'd like to come over and talk with you about you and Janet if I can."

I didn't really want her in the middle of things but figured it couldn't hurt so I replied, "Sure...9ish" and got a smiley face back.

It was already 6 so I grabbed a shower, some fresh clothes and waited. She was there just before 9 and we went downstairs to talk. I could tell she was a bit nervous so I offered her a beer which she accepted with a smile. After a bit of small talk, she finally said, "Janet told me what happened a week or so ago and said she really missed seeing you. The two of you seem so great together so I wondered if you still wanted to go out with her?"

"I do but if you've already talked with her, you know what happened and I'm not sure I'll be able to not try playing with her ass again."

I was expecting her to say that if I really loved Janet, I could do without any anal play so I was totally floored when she said, "Yes, she told me and I told her she should loosen the hell up and let you try anal with her, there's a good chance she'd enjoy it."

She must have seen the confusion on my face because she laughed and said, "Not what you were expecting?"

I grinned and said, "nope!"

"Well, I've been trying to figure out how to say it but I can't think of an easy way so here's what I'm thinking. When I started dating, I decided I didn't want to have sex until I got married, nothing religious, I just want the guy who gets my virginity to also be my husband. That's really crimped my dating because as soon as a guy finds out I'm only going to blow them and make out but not going to have sex, they usually break up with me. Then a few months ago, I went out with a guy who convinced me to try anal sex. I figured I'd still be a virgin so I said yes. The good news was that I loved the feel of a cock in my bum, the bad news was he figured that he could also convince me to give up my virginity and dumped me when I wouldn't. I've got a toy that I use but it's not as good as the real thing but I know how fast news spreads so I also don't want to be known as 'the ass fuck girl'. I guess what I'm saying is I enjoy anal sex but don't want to deal with guys who expect to put it in my pussy too. You enjoy anal sex but Janet's not open to any ass play. What if you and I looked after each other anal wise then maybe you and Janet could get back together and you could stay away from her ass?

I'm not sure if I could have been any more surprised but I had to admit the thought of sliding my cock into Carol's ass was causing my cock to harden. "Gotta admit it makes sense but I don't want to be anywhere around when Janet finds out I've been fucking your ass."

Carol got a funny look on her face and said, "Well, it may not be as bad as you think."

"What?"

"Well, when I told her she should try anal, she said it wasn't going to happen but if I thought I'd like it, then maybe I should get you to fuck my ass instead. Just joking, I said "Good idea, I like the feel of a hard one in my bum and then he won't be as interested in playing with yours."

She continued with "Well, that got a 'I'm not fucking sharing my boyfriend' and turned into a pretty heated argument with her finally telling me I was just a 'butt slut' and storming into her room. The next night, she came to my room and apologized and we talked for a while. She said she'd thought about it a bit and just wanted to make sure that I had no plans to steal you away and that it would just be a physical thing without any emotional connection. I explained that I wanted to stay a virgin until I got married so we wouldn't be having regular sex at all and I was fine that it was just physical."

"Has she said yes or no yet?"

"No, she said she'd think about it but seeing as right now the two of you are technically not dating, how about giving it a try and see what we think?"

By now, I was fully hard and I'm pretty sure Carol could see the bulge in my pants. "Just remember - just like Janet doesn't want anything in her ass, you don't put anything in my pussy."

I told her I was fine with that and said, "Bed or couch?"

With a grin she just said, "Bed!"

My bedroom was only 15 feet away so it didn't take long to get there and almost as quickly, our clothes were hitting the floor. She'd always done her best to hide her lack of tits and ass but naked, she had a very sexy look and the first thing that caught my eye was how dark her areola were and how long and hard her nipples were.

She must have noticed me looking because she said, "Ya, I know - pretty sad when your nipples stick out further than your boobs."

I chuckled and said, "I'll give you that but they're damn sexy - almost too bad this is all about your ass."

After thinking for a second or two Carol said, "Well, I only said nothing goes in my pussy and Janet said no kissing but I didn't say you couldn't touch me."

Hearing that, I reached forward to feel one of her nipples and when she moaned, I took a chance and leaned forward even further and sucked one into my mouth. That got a few even louder moans before she pulled away and with a sexy smile over her shoulder she kneeled in the center of the bed and raised her ass up nice and high.

When I said I wasn't sure I had any lube handy, she just grinned and held up the tube she'd been holding in her hand and then put her head down on a pillow. As I moved behind her, I just had to lean forward and run my tongue up, down and around her darker pucker. Hearing a "Oh fuck, I wasn't expecting that but it feels amazing!"

That was all the incentive I needed to do it several more times, even sliding the tip of my tongue as far as it would go into her bum. As I did, her statement that she didn't want anything 'in' her pussy flashed through my mind so on the next lick, I kept going and traced a line the full length of her pussy right up to her clit. That got another moan followed by, "That feels really good too but right now I want something bigger than your tongue in my ass."

If that was what she wanted, I was quite happy to oblige so after spending a few minutes lubing and opening her ass with one, then two, then three fingers, I was enjoying both the view and feel of her ass opening to accept the head of my cock. I was half expecting her to tell me to stop or at least pause for a few seconds but instead I heard, "Ya, that's good. Fuck me with just the head for a little bit then go deeper."

Damn, I'd always enjoyed the feeling when the head just popped past the muscle ring so I was quite happy to do just that and by the time I'd given her about 30 short strokes, I could feel how much she'd relaxed and loosened so on the next stroke, I slid in full length.

As soon as she realized I wasn't stopping after the first inch or so, she started moaning and the further I slid in, the louder the moan got. When the full 7 inches was in her ass, I slowly pulled back until I was almost all the way out and then pushed back in again.

"Oh fuck ya, just like that! Long, deep strokes, I love feeling my ass opening to take you in."

Holy fuck, I'd never have thought that she'd be that vocal but I was loving it. As I fucked her ass, I could hear what sounded like her fingering her pussy and after a few more minutes her whole body clenched, she let out a loud "Ohhhh, ya!" and then she relaxed again. When I asked if she'd just cum she said, "I did! I don't always cum when I'm getting it in the ass but when I do, it seems way more intense."

We fucked like that for a bit more before I pulled out and said, "How about you roll over?"

As she rolled onto her back she said, "Just remember, not in my pussy!"

"Oh don't worry, I'm totally loving the feel of your ass around my cock, I was hoping I could watch you play with yourself until I cum."

"Mmmm, that sounds like a plan!"

Now I had an even better view; fingers from one of her hands rubbing her clit, fingers from the other thrusting in and out of her pussy and her ass clinging to my cock as I pulled back and then spreading when I thrust back in again. With a combination like that it's hard to hold back and as much as I tried to hang on, all too soon I was erupting inside her ass.

As I softened and pulled out, there was a small, 'pfft' followed by a trickle of cum from her ass. Carol giggled and said, "wow, you did fill me up!"

We both laughed a little at that before she got up to go to the bathroom. When she came back, she said, "Well, whether or not you get back together with my sister, I'd love it if we looked after each other's anal urges on a regular basis."

"Me too, that was awesome!"

A few days later, I got a short text from Janet that said, "I'd really like to talk, can I come over?"

As soon as we were downstairs, I held her hands and said, "I'm sorry about what happened and I really miss you!"

That started a flood of "I miss you too!" and "Can we try again?" with lots of hugs and a few kisses in between.

Eventually I had to say, "You do know your sister came over the other night to talk to me about us getting back together?"

She got a bit of a funny look on her face and quietly said, "Yes."

"She told me that the two of you had talked and what she was thinking as a solution. I really..." then she cut me off with a finger on my lips followed by a long kiss.

"I don't know why the idea of anything anal turns me off so much but when I thought about it, I realized that if I hate it that much then it's reasonable that you would enjoy it that much. I've been thinking about it since Carol and I talked and even more since the two of you talked. I know lots of people would say it was wrong and I'm still not sure it'll work but I'm open to giving it a try with a few conditions."

I'd been expecting a total, "No" so I was quite surprised and now curious as to what her conditions were. "Ok, what are you thinking?"

"Well, I know it'll be happening but I don't want to know when or anything else about it from you or Carol."

"Fair enough, what else?"

"She's guaranteed me she wants her first actual sex to be when she gets married so I'm not worried about the two of you having sex and it may sound strange but I don't think I could handle the thought of the two of you kissing or doing anything else for that matter."

"No problem there either, what's the last thing?"

"Well" and she hesitated a few seconds before continuing, "If...and that's a big IF, I ever decide to let you put anything in my bum then I get to do exactly the same thing with you."

I had to think a few seconds on that one before replying, "Ya, that sounds fair too." and then as an afterthought I added, "and what's the chance that if I let you finger or toy my ass that you'd be more likely to let me do the same to you?"

That got a bit of a smile and a reply of, "No guarantees at all, but it's a possibility."

"I'd say that all sounds reasonable. Does that mean we're dating again?"

With an even bigger smile Janet said, "Well, that depends on how many times you make me cum in the next couple of hours."

I wasn't going to argue that and after a flurry of clothes hitting the floor, we were both naked on the bed. After enjoying just kissing and touching for a few minutes, I shifted so I could give her a good licking and found she was completely shaved, compared to the 'trimmed' look I was used to. I'd previously suggested that she went bare but she'd always said no so to show her how much I enjoyed it, I spent at least the 10- or 15-minutes licking, kissing, sucking and nibbling her to 4 maybe 5 orgasms and then moved up to kiss and suck her nipples while I fingered her to a couple more before she finally croaked out, "ok, enough for now".

I was good to keep going but when I looked up, her eyes were half closed and she whispered, "That was amazing and I definitely want more but I think I'll need a few minutes to recover."

That worked for me so she rolled against me and we spent the next few minutes hugging and gently kissing before I finally felt her reach down to fondle me saying, "I'm ready if you are."

I certainly was so when she rolled back over, I rolled with her and at the same slowly slid my full length inside her pussy. It had been less than a week since we broke up but I'd totally missed her smile, her kiss, her touch and of course the feel of her hot, slick pussy around my cock.

Depending on her mood, sometimes she'd cum harder from long, slow strokes and sometimes she'd cum harder from a hard, fast pounding and when she kept telling me to go harder, I knew which one it would be today. I lifted her legs a bit higher, thrust a little harder and sped up until there was a slapping sound every time our bodies hit. In less than 5 minutes I could tell it wouldn't be long before I came. I tried slowing down to make it last but every time I did, she told me to fuck her harder. A few minutes later and I was filling her pussy with cum but rather than slow down like I usually did, I kept fucking her hard and fast as I came until she exploded in orgasm as well.

Both of us were sweaty and breathing heavy when I rolled off and lay beside her. Janet rolled slightly so we were somewhat facing each other and whispered, "That was amazing, I told mom and dad we'd likely be getting back together and that if we did, I might not be home tonight. Would you like me to stay?"

We'd never spent the whole night together so that thought alone was enough to make my cock twitch and the feel of her running her fingers the length of my slippery cock got an even bigger twitch. With a bit of a chuckle she whispered, "I'll take that as a 'yes'?"

"Most definitely a yes!" and with that I pulled the blankets up over us and we curled up together. A while later I realized a few things, I'd dozed off, it was almost two hours later than the last time I'd looked at the clock and Janet's mouth and tongue were doing an awesome job of getting me hard again. It was the last one that surprised me the most because even though she loved giving head, she'd never done it after we'd had sex unless we'd showered because she said she didn't want to taste her own pussy juice on me.

Eventually we curled up and went to sleep with the hopes of an early morning blowjob before she had to go back home. As it was, I did wake up to the feeling of Janet's mouth and hand on my cock which was already nice and hard. Just when I was thinking that my hopes from the night before were going to end up happening, she stopped, looked at me and said, "I could keep going until you cum but I really want to feel you cum inside me before I have to go home."

I had no problem with that so I stayed where I was and Janet climbed on top and rode me. By the time I was getting close, she'd already had one orgasm and her second was almost at the same time that I came. We cuddled for a while before we got up, had a shower and headed home.

The next few months were a wonderful mix of sex, everything but anal with Janet and initially anal only with Carol but eventually not only did we start kissing, we also started enjoying each other orally as well. Neither Carol nor I every told Janet of anything we did and she never asked.

We've all been told that 'all good things come to an end' and it was almost 9 months later that Carol found who she was pretty sure was her 'one' and decided that if she was going to be serious with him then she'd have to quit meeting with me because he was doing a great job of keeping her anally satisfied. I kinda hoped that somewhere along the way Janet would decide to at least try anal sex but when Carol and I stopped getting together, she made it clear that nothing had changed and anal sex was still out of the question. When I somewhat jokingly suggested that I might be able to find someone to replace Janet, I got told that it had been hard enough knowing that her sister and I were doing it so there was no way she'd be able to handle someone she didn't know doing it with me.