Reuben's Surprise

We all have first times, well maybe not all, but us lucky ones will remember it for as long as we can. Me, well it might have come later than normal, I was never that lucky with the ladies when I was back in high school, but the way in which it came about, I would not change at all.

It was one of my closest friend's ideas. He later told me it came to him because he was sick and tired of having one sided conversations. Ever since high school he had been telling me stories of his exploits, and all I could do was listen. At first you would think he was bragging, maybe even making it up as he loved having an audience. But if you knew him as well as I did, you would know it to be the truth. He was unashamed and would go into as much detail as his audience demanded, even if it would show him in a slightly embarrassing situation.

"Hey Daniel! Tell us again how you creamed yourself before you could even start", one of the bullies would laugh.

Daniel would just have a slight grin when replying. "Yeah maybe when you can eventually get someone to allow you to even touch her beforehand, you might do better. Maybe you can tell me in ten years, if you even get a chance by then."

I used to think about his stories when lying in bed, imagining myself in his shoes, doing anything and everything he did to all those women. Every night my imagination would match his stories and experiences, while his stories got more involved and advanced over time, so did my fantasies.

A couple years after high school he eventually got bored of having one sided conversations, and one day confronted me directly.

"Reuben! When are you ever going to get laid? I want to talk about these things together, it's boring with one person doing it alone."

He smirked at me when saying that last sentence and I didn't know if he meant it as a playful jibe at me having to go solo, or just plainly talking about how boring it was when, he alone, was telling stories. Knowing him, it was probably both.

Embarrassingly I told him that I was just too nervous to seek things out. That it was getting harder and harder to go through with it because my lack of experience was psyching me out.

"Anyway." I continued. "Even if I did go all the way with some chick, I'll probably be too embarrassed to even talk to you about it."

"Nonsense!" He exclaimed. "I'll make sure that when it happens you'll find it easy to talk to me about it."

I remember being in disbelief when he mentioned that, but I did not know just how easy he would make it.

A couple days later Daniel invited me over to his place. He was very adamant that I come over, but would not tell me why. Also, having no idea that he was planning anything was probably for the best, as I would have found a lame excuse to miss it.

On arriving at his place, Daniel invited me in. He seemed a little more animated than usual and practically pushed me into his room with the promise that he was going to show me something.

I was pretty startled to find that I was not alone with Daniel. He didn't mention having other company over, and this was not normal company either. It was Hailey, Daniel's girlfriend. Well I wouldn't call her his girlfriend, more of a friends with benefits type of person. I had met her once before at a party, but by now I knew quite a bit more about her than a normal acquaintance would. Daniel often spoke about Hailey and what they would get up to together.

"Hey Reuben!" Hailey shouted, smiling at me while coming in for a hug. "Nice to meet you again."

Curiously I looked over at Daniel while hugging her and made the best reply that I could muster. "Hi."

You see, I had a strong crush on her, probably developed by all the stories that Daniel would share with me. How she moaned when Daniel thrusted in her. How easily she could get off with just the application of his fingers. How her long brown hair would get all matted up and sticky from a facial.

Many a night would I picture her under me; her small feet on my shoulders, my hands on her subtle breasts, all the while I effortlessly entered her. How tight it would feel and how smooth it was as she had not a single hair below her neck. I would just last a few minutes on this fantasy alone before having to clean up my own sticky mess.

"Reuben, you remember Hailey right?" Before I even had a moment to answer, he answered for me. "Sure you do, from all those stories I would tell you about her." Now I was embarrassed, how could Daniel say that in front of her? Surely she would figure out that I would think about her intimately.

"Oh don't worry." Daniel continued as he saw my shocked expression. "She knows I talk to you about everything."

"Yeah, don't worry." Hailey replied quite playfully. "I kind of enjoy knowing that what we do is not a privately kept secret. In any case, Daniel and I talk about you too."

I was at a loss for words. I felt quite vulnerable. What did she know about me? What did Daniel tell her, that I was still a virgin? That I would jerk off thinking about her (Daniel must know that I do)?

Hailey now grinned at Daniel. "You were right, shame, look at his face, he looks so innocent and sweet, I can't wait to start."

"Yeah, come on Reuben, don't look so shocked. I told you I would get you laid sometime, and that time is now. We're going to have sex, right here, right now. You, me and our dear friend, Hailey."

I struggled to reply, trying to mouth and form words at this point was difficult. Was this a joke? A dream? I did manage to catch one part though, one main part. I put all my energy and strength into saying this one word. It came out soft, but the meaning was clear. "We're?"

Hailey was the first to reply. She sat down on the bed still facing me. "Yeah that's right, you're a virgin, I've never been with a virgin and Daniel has never been in a three-way. It's a first for everyone. A win, win, win."

That was true as far as I knew. I had never had sex. Hell, I had never had a release that wasn't self-induced. Daniel had never once told me about a threesome that he had, so it must mean he has never had one as he would have definitely told me. So assuming those were true, then it must also be true that Hailey had never been with a virgin. It would only occur to me later that she heavily implied that she had been in a threesome herself before. I'm kind of glad I didn't catch onto that immediately as that would have distracted me more.

Thereafter it seemed that Daniel was the one taking charge and that both Hailey and I were just following instructions. It made me feel closer to Hailey and also made me feel slightly less insecure about the whole situation.

"Exactly, and this way if any early 'spillage' happens with either one of us, the other could take over." I knew what Daniel was implying and I'm grateful that he both mentioned it now and did not actually point it out that it was more than likely that I would have the early release. The way he said it made it seem like we were on equal footing. "Also you won't be embarrassed talking to me about it afterward as I was involved in the whole thing with you."

I still had barely said a word since the announcement that we would be having sex. That I would finally lose my virginity and not only that, that it would involve a threesome. I wasn't sure if I was even ready for all this to happen now. I tried coming up with an excuse or something, but I was frozen. It was then that Daniel took charge.

"Reuben just stand there for now and kick off your shoes. Hailey will help with your pants."

This I managed to do, but not with the ease that it should have been. I had one shoe off and was about to toe my other shoe off with my foot when I felt Hailey in front of me. I almost lost my balance as I felt her reach out to unbutton and unzip me. Still sitting on the bed, she gave a firm tug and shortly my pants fell down to my ankles.

I stepped out of the leg of my pants and at the same time kicked off my remaining shoe. I was now standing in my shirt, socks and underwear with Hailey sitting down on the bed, her head at the exact height as my underwear. Having no idea what she would do next, I held my breath in suspense. Would she suck me off?

She was really close to me now, her head mere inches away, but she held my gaze, smirking all the time. That was when I started feeling apprehensive. Am I even hard? In all this excitement, my brain did not register anything. I was scared I would be one of those people who couldn't get it up when required.

Before I could continue with those thoughts, I felt my underwear being tugged down from the rear. I had forgotten that Daniel was also there and he was the one who finally stripped me down.

"Oh yeah, he's ready." Hailey was so close to me that I felt her breath as she directed this statement to Daniel. My fears were put to ease, I was definitely hard.

"Now Reuben, you are not to touch yourself in anyway. Don't want you ruining the whole experience now, do we?" This instruction came from Daniel, who was now almost completely naked, having left only his socks on. He walked back to the bed and sat behind Hailey and pulled her backwards into his arms.

As she moved away from me, Hailey lifted up the bottom of my shirt and dropped it so that it would partially cover me up. I was completely hard and sticking straight up, so my shirt managed to cover quite a bit past the head. The fabric touching me and the fact that I did not drop it myself caused a slight throbbing to occur. I fought the urge to touch myself, even just a little.

I had only managed a glimpse of Daniel earlier and now that he was sitting directly behind Hailey, I couldn't see much more. But I was more focussed on the fact that Daniel was taking off Hailey's top.

Her arms in the air, Daniel lifted her top off in a quick motion leaving her bare from the waist up. She had apparently not worn a bra. Daniel's left hand then went down towards her left breast and carefully cupped it. His other hand went lower and started taking off her pants.

I was mesmerized and didn't know where to look. Do I look at her pants as they're coming off? Or do I look at her right firm breast? Or maybe even look at her other breast and watch Daniel, who was now slowly tweaking Hailey's nipple, playing with her.

I decided on gazing at her pants. I figured that as I had never seen a fully naked woman before (apart from porn), that I should take this opportunity and see her fully revealed.

The right choice was made. Hailey was wearing loose fitting shorts. When Daniel's hand reached into them to take them off, I could tell Hailey was looking directly at me when she gave a slight, but maybe exaggerated, moan. Her pants easily fell off and she was in fact not wearing anything else. She was completely naked, and true to Daniel's stories, completely hairless down there.

The way that Daniel took off her pants, from the front centre downwards made it so that his hand was mostly obscuring what I desperately wanted to see. I'm pretty sure they planned this so it would have maximum effect on me. This was further proven as Daniel started raising his hand ever so slowly. His middle finger lingering behind until it was caught in the folds of her 'lips'.

Once he reached the top, his finger popped out and I let out my breath that I did not know I was holding. Both Daniel and Hailey gave a small laugh at the sound I made when I released my breath. Their laugh did not phase me as I was intently staring at Hailey's most intimate parts. I dared not to blink for fear of missing out of even one second of this glorious display. I never felt as aroused in my entire life as I did right then.

My erection was still partially obscured by my shirt, the type and colour of which made it easily highlight any type of dampness on it. It was grey, and in my obvious bulge, you could see a much darker spot where I was beginning to leak. Now usually my circumcised penis does not produce too much precum when I masturbate, and if it does, it's only after a really long session. But now, without any manipulation, I had already started to produce some, and it was quite obviously being absorbed into my shirt.

I was still completely focused on the imagery when Daniel pulled Hailey's head onto his right shoulder. Both still facing me, Daniel took his left hand and while sitting behind her, reached around and inserted his finger into Hailey once again. From my position I could see almost all of Hailey, her breasts and her smooth and hairless pussy, which was now being fingered. Of Daniel I could really only see his face, left arm and the back of his hand. It was his hand that I focused on the most, mainly because of what it was doing.

He started quite fast, his middle finger rubbing up and down while also shaking his hand so his fingers would a vibrating sensation. I couldn't tell how deep he was penetrating her, but it looked like it wasn't too deep, maybe up to his middle finger's first knuckle. He must have done this before as it had an instant effect on Hailey. She lifted her pelvis slightly and made a slight moan of pleasure. Her head fell further back onto Daniel's shoulder causing her to push out her breasts a bit. Her breasts weren't too big, but I've never really liked big ones. Her ones were perfectly sized for me, big enough that I could cup each one in my hand completely.

Daniel kept at it for a good minute or two, at a decent speed making sure Hailey felt each twitch and motion of his fingers. He was moving his hand up and down along the length of her 'opening'. By this point it looked like Hailey was trying to gain back some control that she had lost to the pleasure she was receiving. She sat forward a bit and closed her legs in order to slow down Daniel's manipulations. He did slow down, but I think the loss in pleasure instantly made Hailey open her legs again.

Daniel continued at a slower speed for a bit, but it did look like he was applying more pressure and going deeper. Hailey was now starting to moan. Actually it was maybe a sort of a combination of a squeak and a moan. I remember it being very cute considering what was happening. Her face also looked pretty hot now, it was like she was grimacing from some pain, but it was something else. She wanted him to go faster it seemed.

When Daniel eventually started to go faster, her cries increased in response. She now had given herself to the pleasure she was receiving from Daniel's fingers. She looked so lost to the pleasure, that she might have forgot that I was even there. I thought this as I felt just as lost, standing there staring at them with the hardest erection in my life wearing just my socks and shirt.

Suddenly Hailey cried out and jumped forward somewhat. My complete lack of experience made me think she had just had an orgasm. It was now when Daniel spoke to me again. "I'll need some minor help bringing her over the edge." Smirking the entire time at me he pushed Hailey down so she was lying backwards on the bed over his legs.

"Take off your shirt and grab her feet," he directed at me. He had positioned her so I had a perfect view on only her pussy and legs. "Hold her feet up and apart so you can see everything."

Like a lamb I followed his instructions to the letter. Taking off my shirt, then grabbing her bare feet to force her legs apart. I was in a trance, here I was eventually touching a completely naked woman. I know it was just her feet, but they were soft and warm to the touch.

I stretched out my arms to pull her feet as far apart as I could, opening her up even more. This allowed Daniel to have more room for his fingers to penetrate her, but it was also giving me a perfect view of everything. In this position I was so close that I thought some of my leaking dick would actually drip on her. However, I couldn't really tell if that actually happened, as at this distance I could see how wet she had become, and any additional fluids would not be noticeable.

This natural lube of hers allowed Daniel to go at full speed. Expertly rubbing her up and down, while his middle finger and two nearby fingers were almost fully inside her. Hailey's cries were ecstatic and I now realised why Daniel wanted me to hold her feet. Her toes were twitching and curling, while her entire feet shook in conjunction with her whole body. She tried closing her legs multiple times, but with my grip on her feet she stopped each time. Unable to close her legs to slow down Daniel's motion, she started thrusting her pelvis up to meet Daniel's fingers, to try and get more of them inside her.

When she started thrashing about from the pleasure that she was experiencing, I decided to slightly massage her feet with my thumbs. I gripped her feet in such a way that my thumb was just under her middle toes. Applying some pressure I ran my thumbs in small circles. This way, it felt like I was at least doing something. Although, I don't think she even noticed what I was doing because of Daniel's expert fingering.

Daniel now had all four of his fingers rubbing up and down at a rate that even her thrusts couldn't match. Going like this she didn't last long until she gasped out a final "Yes!" I correctly figured out that she was climaxing.

It was amazing, I could feel her orgasm from just my grip on her feet, her toes twitching erratically, while flexing the arches of her feet. In her last throws of her orgasm, she had lifted her whole pelvis up - in order to get as much of Daniel's fingers inside of her. So reared so far up that I had trouble gripping both of her feet as she had to spread her legs wide apart.

Daniel had slowed down completely and now without his blurred hands in the way I could fully see how wet Hailey had become. I figured girls could get this wet, but seeing it was something else. Daniel took off one of his socks and used it like a small towel to dry Hailey. You could even see the dampness on his sock grow after each wipe.

I had let go of Hailey's feet by now, but was still mesmerized by the entire sight and experience. My balls were aching by this point as well. It was then that Daniel looked at me directly and gave a small smirk before whispering something into Hailey's ear. She still wasn't completely aware, but managed to open her eyes and look at me as well.

Repositioning slightly she stretched out her leg until I felt something warm, but damp, press against my dick. I remember distinctly gasping out loud and looking down at the same time. It was Hailey's left foot pressing directly on me. The dampness however, was from me. All the precum that I had been leaking the entire time was dripping down my shaft. With it acting as a lubricant she firmly pressed her foot down and moved it up until her toes curled around my head. She wiggled her toes and continued to press firmly for a couple seconds, but those seconds was all it took.

I came, and made slightly embarrassing grunting noises each time I shot. Her toes were fully covering my slit so each shot of cum couldn't go anywhere, so it spread under all her toes. Some of it even seeped through the slight gaps between each of them, but most of it coated the underside and dripped down onto the rest of her foot.

After a short time Hailey pulled her foot away and held it up directly at me so I could see it dead on. She moved, straightened and wriggled each of her toes showing me my own cum as it stuck to her. You could see strands of cum stick in between her toes, like a webbing, even though she was spreading them apart and moving them as individually as she could.

I didn't even notice that Daniel had moved until I felt him cleaning my dick. He was wiping me with the same sock he used earlier to wipe Hailey after her orgasm. He even squeezed me through his sock to get the lingering drop or two out. Daniel then pushed me to the bed and told me to sit down or lie down before I collapse.