Life's journey

Meeting Sam

I had noticed some change in Jake since he had moved in. Firstly, since Felix had left, he has become more relaxed, more like the house is his and no longer the third person in a relationship which of course he was. Moving into my bedroom and sleeping together has helped that too. We always find intimate personal moments throughout the day, I give hm a nice feel-good massage while he lays by the pool, with cream and oil to enhance and protect his skin from the sun but still allow him to tan up all over. He now has the most beautiful golden tan, full body. When we first go to bed each night he lays next to me, chest to chest, we kiss passionately and I caress his back and ass which we both find a big turn-on. It is amazing how something as basic as holding a beautiful ass in your hands can be so fulfilling.

We had not heard further from Van or Paulo since meeting then, it was more surprising with Van as he is at a loose end until University returns in Feb. Paulo on the other hand works full-time so he may be just busy with that – Jake and I agreed we would touch bases with Paulo in a week or so.

Sam was a surprise, originally, I thought he was a player and after having him over I thought we may have scared him off. He messaged us a few days later asking if he could come over again. Jake arranged for him to cover over after I finished work, we said he could stay the night if he wanted.

It was a much more relaxed and confident Sam who knocked on the door second time around, now familiar with us and our surroundings. We had a drink and asked him what he would like to do on this occasion. He said he would like to suck Jakes cock again and even try fucking him.

We headed out to the pool area, Jake set up our trusty padded apparatus for him to be comfy in the doggy position and we all got naked. We said we would coach Sam through it all and to ask any questions as we would rather teach him good than bad habits so that he always pleases both himself and the bottom.

Good preparation in this case would include Jake sucking Sam till he was hard and myself eating Jakes ass to open him up, and xplained that this also gets us in a good frame of mind to perform well. Sam laid on the couch and Jake crouched over him and starting to stroke him. Jakes crouching position gave me great access to his ass and I started to lick his hole applying some lube as I went.

Once he had stroked Sam somewhat hard Jake took his cock into his mouth and took him deep until he was fully erect. Jakes ass could be breakfast lunch and dinner for me, I could honestly eat it all day.

It was time for Sam's first ever man fuck, Jake made himself comfortable on the padded apparatus while I lubed up Sam’s throbbing cock. “Always be aware of what the bottom is feeling till you know them well” I said to Sam. “Hold you cockhead against Jakes hole, rub it up and down his annus” I continued. Sam did exactly as I asked. “Fuck me” instructed Jake. “Push only the cockhead in, hold it and make sure he is feeling comfortable” I told Sam. “Now push another inch or so and hold it” . “How does it feel” I asked Sam. “Tighter than a chicks pussy” he laughed. “That’s why you got to know how to do it properly” I responded. “Keep repeating that until you are all the way in and hold it there” I said. Sam duly obliged. “Feels good” said Jake, “got for it” he instructed.

“Now Sam, I want you to slowly pull out until only your cockhead remains inserted and hold it that position” I said. “Hold for 15 seconds then slowly push all the way in. Keep repeating that but don’t go faster or you will cum too soon”. Sam was very rigid and mechanical in the way he went about it, not a lot of passion, I guess that was the scenario of being coached through. “Imagine your driving a car with six gears, so far you have been in first only, time to move to second gear, so push in a little faster and harder and hold for less time before withdrawing” I instructed. Sam was doing a good job. “Do you feel like your gonna cum” I asked. “No I am fine” he said. “Ok well take it to 3rd gear” I said. It was good to watch a first timer having a crack at fucking ass, I had never seen such myself. Sam was concentrating hard not deviating from my instructions. “If ya still feeling good get it up to 4th gear” I said. “That’s better” cheered Jake now enjoying what felt like a pounding rather than a massage. “Can you find a 5th gear” I enquired. “Yes, but I think Iam about to cum” responded Sam. “Where do you want his cum Jake” I asked. “In me and in me only” demanded Jake, obviously keen to be the first person Sam seeds.

“I’m cumming” said Sam as his body shuddered and exploded into jake. “Make sure you empty fully before withdrawing” I told Sam.

Sam and Jake laid on the couch “Congrats mate” said Jake as he gave Sam a high five. “You did a great job for a first time” I said as I headed inside to retrieve some refreshments for them.

‘Would you like to experience how anal stimulation feels” I asked Sam. “Yeh, but I have never had anything up my as to take it easy” he replied. “It will be a massage, we stop when you say stop,” I assured him.

I retrieved a pillow from inside and got Sam to lie face down, ass in my lap, legs outstretched either side. I dripped some oil over his back, ass cheeks and into his crack. I have him a good 15 minutes should and back massage before moving to his ass cheeks. “I’m going to lightly caress the outside of your annus now, so just relax and enjoy” I forewarned Sam. I brushed my finger ever so gently over his hole and surrounding areas, slowly adding a little more pressure. He seemed to enjoy as he opened his legs wider, I could also feel his cock hardening in my lap. “So far so good” I thought to myself.

“I’m going to gently enter you, is that OK” I asked. “Yes but be gentle” he replied. “Just focus on relaxing your ass muscles and breathing”. Ever so gently I pushed my lubed index finger into him, he jumped at first but after further reassurance to relax and focus on his breathing I was able to enter more easily. “I’m going to use the same technique with my finger as you did with your cock to Jake, but stay slow as it’s a massage” I advised him adding “my finger isn’t that long”.  I gently pushed my finger in, holding it and then withdrawing it time after time for several minutes.

“How are you feeling” I checked in. “It hurt when you first entered but now I am used to it feels really good, so relaxing” he responded. “With us its always about one’s comfort and pleasure” I assured him before adding “your cock sure feels like he’s enjoying it”. “I’m as fucking hard as!” he said, “is this how it is supposed to be?”. “Yes Sam” Jake and I responded simultaneously.

“While your feeling good and your ass is open and receptive, would you like to try cock” I tentatively asked not knowing what reaction I would get. “Yeh, I wanna know how I made Jake feel” he surprisingly responded. “Bare or condom” I asked. “Bare like Jake” he said again to my surprise.

My cock was had and ready to go having had his pressing against it. I got Sam to kneel in an upright position, legs as wide as possible, I got him to watch as I applied lube to my hard cock. “I’m going to do exactly as you did to Jake, it will hurt initially more than my finger because my cock is wider, so relax your body, focus on your breathing then the pleasures will come”.

I rubbed my hard cock on the outside of his hole, “Are you ready I asked’. “Yes” he said so I pushed my cockhead into, he burst out a cry of pain, Jake and I continued to reassure him to relax and focus on this breathing. “Do you want me to stop” I asked. “No” he said. I pushed in inch by inch stopping each time for him to adjust. Jake continued to coach him through his feelings. “I am all the way in now” I said as I held then started the withdrawal process. I continued the same method as I had coached him through when fucking Jake. I told him 4th to 6th gears were for another day as I moved into 2nd and then 3rd gear.

My cock was feeling as if it was being squeezed to death such was the tightness of his ass as I knew I would be blowing soon. “Where do you want me to cum when the time comes” I said. “In me same as Jake” was again the response. “When I’m going to cum I will go a little harder to bring it on” I advised as I reached around to feel his cock which was still hard as concrete. I began to stroke it, this bought on some heavier breathing and moans from Sam. I made sure I was jerking him at the same speed I was fucking him.

His body started to go into overdrive as did his moans, I felt his ass muscles contract around my cock, “I’m gonna cum” he said, I quickly upped the pace so we would both blow concurrently. I felt his cock shoot his loads on the towel below, I fucked him harder and within around 2 minutes I felt myself unloading into his ass.

Jakes help Sam to a resting position, again offering the big high five, “you have been seeded mate” he declared to Sam, “how does it feel?” he asked. Sam was still catching his breath and have a few mouthfuls of drink before responding. “I didn’t know what to expect, but it was different to what I expected” he laughed as his own nonsense. “That was amazing, so happy I have had man to man love” he added.  “No, you have had man to man sex” I said “now you know what you’re doing you can work on man to man love” I added.

I walked Sam over to our outdoor shower and rinsed him clean lushing out my cum from his ass. “I’m gonna sleep well tonight” he said. “Stay over?” I asked. “Sure can” he affirmed. Jake had meanwhile cleaned up the area we had been playing, took our clothes inside and prepared our last drinks for the day.

We all climbed into our bed, me spooning Jake, cock resting against his ass and Jake spooning Sam, cock resting against his ass.

We slept well.

As tends to be the case with a full bed, once one awakes, all awake and this was the case. I reckon Sam had good dreams as he was as hard as a rock. Jake noticed and asked if he could help him out. Seizing the moment Jake lubed himself up and climbed aboard Sam’s pole, letting him experience being ridden for the first time and the fuckee driving the experience rather that the fucker.

I smiled and headed for the shower as it was a workday ahead for me. On my return to find some clothes for the day there was Sam now riding Jake with Jake coaching him through it.

I headed for the kitchen for my morning coffee and then to the inside office to start work.

About 20 minutes later Sam came into the room, naked and thanked me for last night. He had remembered my words from last night and asked if he could come back again so he could turn “sex into love”.

“Your welcome anytime Sam” I responded.

Sam dressed and headed on his way, Jake entered my office, again still naked. I pushed my chair back. He climbed on nd sat on my lap facing me, put his arms around me and said “Love you JA” before kissing me on the lips. “Love you too Jakey” I said adding “its your birthday this week we got to do something special”.

“Let me think about it” he said before kissing me again.