Mike Finds Himself - 19. Who Becomes an Enthusiastic Bottom? / Readers’ Choice

Following Mike asking, Have you ever fucked or considered being fucked?, Bob replied, “Yes and No! Early in our relationship, Chuck made it very clear that he wanted to give his ass to me. At first I was hesitant. Then just to please him, I did it. Eventually, I became a lusting top that resulted from the combination of his passionate reaction to my making love to him and the wonderful feeling my dick received. My entire body tingled as I topped him. Having our bodies coupled that way was pure bliss. Sometimes in the middle of the night, I would wake with his body spooned against mine with my dick at his crack. The invitation was obvious. Without a word I would slip in as he opened to me. Following a gentle fuck, I would fall asleep still in him. In the morning, we would wake in a mess of pleasure. We got used to waking with stained sheets resulting from my cum that had dribbled out of him and his from cumming as I fucked. We put a plastic cover over the mattress under the padded mattress pad so as not ruin the mattress from the juices of joy.”

“The subject of his topping me never came up by word or action. My pleasure came from making him, my dick and my entire body happy. What we were doing was wonderful and we never considered reversing. So the basic answer is, Yes, I have never been fucked. NO, I have never desired to be the submissive one.”

Mike responded, “I told you about my encounters prior to meeting you. However, I omitted the fucking part. Both Alan and Farmer Bruce were bottoms. Alan taught me the joy of fucking which made my dick very happy. Doing it with him was an athletic exercise, basically bam, bam and cum. Fucking Bruce gave me a totally different feeling. With him it was not just a sweaty fuck, but an expression of desire. As I told you earlier, with Alan I felt only lust while with Bruce I felt emotional connection. With the strong feelings I had for Bruce, the entire sex act, not just the fucking, was total passion.

Bob replied, “It appears we have both had experiences of loving emotion being expressed by our coupling in the most intimate way possible. I wonder. Are we both having the same thought? Does each of us have a desire to express our love in this way?”

Mike wrapped his arms around his love, “My fantasy is to couple with you. The fantasy alternates between you ravishing me and me pounding your ass.”

“Shall we continue this discussion this evening? Right now my balls are turning blue from anticipation.”

The two continued their edging adventure (which began in the previous chapter), culminating with Mike kneeling over Bob while cumming on his dick and balls. Bob then used Mike’s cum to lube his dick and blast onto his own chest.

After playfully showering together, they dressed in in their conservative office attire.

Both had trouble concentrating on their work. Mike eventually sent Bob an email: Our project this evening could get messy. After work I will pick up appropriate supplies.

Bob sent a reply: Using my laptop, I found a site that discussed how beginners should prepare for our project. Will share it with you at home. While Bob was using his personal laptop, he knew Mike was sending and reading emails on a company computer. Therefore, neither sent messages that might contain inappropriate or embarrassing material.

Note to Readers – the website Bob found with first time information was: https://endinghiv.org.au/blog/10-t,ips-for-first-time-tops/

On his way home from the office that afternoon, Mike, wanting to be incognito, stopped at a pharmacy where he had never shopped. He had assumed that a condom was just a condom and was overwhelmed with the selection of brands and types. He did not want to loiter in the family planning aisle, so he quickly grabbed a box of Trojan Double Ecstasy Lubricated Condoms, as well as a tube of K-Y lubrication. While he was embarrassed to place his purchases on the counter at the checkout, the middle aged female clerk showed no emotion.

Bob was already home when Mike arrived. Usually, they would discuss their day at work while preparing supper. This evening was different. Bob’s laptop was on the counter displaying the ‘first-time-tops’ site. As Mike read the material, Bob stood behind him massaging his shoulders, then moving down to the nipples, abs and finally, dick. Supper was forgotten and the two soon found themselves in the bedroom. In a frenzy of passion each undressed the other. Then naked, facing each other with precum oozing dick heads that were kissing, both realized they did not know how to proceed.

After ‘eye fucking’ each other, Bob commented, “At this point the fucking should begin. The site recommended that for a first fuck the top should lay on his back in what is called the cowboy position. After rolling on a condom and lubricating the hard dick and ass, the bottom should kneel facing the top, reach back and aim the dick to his hole. I assume this position is suggested so the guy being impaled is in total control as to how fast and how deep he receives the dick. So, which one of us gets on his back and which one gets fucked?”

Following a period of silence, as the two hard dicks began to deflate, Mike suggested, “Let’s flip a coin. Heads, I lay on my back and you, my friend, get fucked. Tails, I get fucked.”

Mike reached for his pants and took a quarter from the pocket. He handed it to Bob who flipped it into the air. The coin landed on the floor and rolled into the corner. The two naked guys got on their hands and knees to examine the coin showing its TAIL side.

Taking the advice of the website with first time bottoming information, the two had agreed the cowboy position (the top on his back, the virgin bottom lowering down) seemed to be the most comfortable position for newbie bottoms to start a session. The site stated, ‘This is also a great position because it allows pretty good angle control. Your partner can position themselves to make the most out of your member’.

As Bob stood and then laid on the bed on his back, Mike opened a condom packet and rolled it on his love’s now revived and eager dick. Mike, with some reluctance, mounted the bed. He opened the tube of lube and generously greased his ass and Bob’s dick. As Mike knelt facing his friend, his dick totally deflated. He wondered if the softening resulted from fear of the unknown and possible pain from being impaled. Gingerly, Mike reached behind and reached for Bob’s hard shaft, placing it against his hole. Then leaning back, the generously lubed dick slid less than an inch (2.5 cm) into him. There was a very uncomfortable feeling down there accompanied with some pain. While the pain was moderate, he realized there could be more as the dick had barely penetrated him. Mike gently pushed down as the dick slowly slid in. The deeper the dick, the greater the pain.

When he assumed Bob was about half way in, Mike leaned forward resulting in Bob’s piece sliding out. “Let’s try again. Please do not move. I need to control how fast and how far you go. Although it hurts, I want you all the way in, eventually.”

The lack of action and concern about Mike’s pain resulted in the softening of Bob. Bob reached for his dick and jacked it hard. Mike started the process again. He reached back for the now hard shaft and placed it against his hole. He then slowly leaned back forcing Bob deeper and deeper. He no longer could ignore the pain. He raised himself and Bob’s dick fell out.

“I’m sorry. I thought I could continue, but the pain was too much.”

Bob pulled his love down next to him and held him. He whispered, “I love you so much. I do not want to do anything to hurt you. Maybe it won’t happen. That changes nothing about my feelings toward you.” For about fifteen minutes the two remained wrapped in each other’s arms.

Finally Mike spoke, “Right now, my ass still hurts like hell. Would I be willing to ride you again? My ass says ‘no’, at least as for now. How will I feel later? Who knows? Let’s go out to dinner. Right now, a change of scenery would make my ass feel better.”

As the two sat in a booth at the Olympia Diner eating dinner size chef’s salads, Mike whispered, “Thinking of me being on top is causing nice feelings below the belt. Hopefully my dick will work better than my ass. As soon as we get home, it’s my turn.” He picked up his bottle of beer holding it in a ‘cheers’ position. Then he said, “I need extra strength so I can give it my all. I’m going to have a piece of lemon meringue pie. Join me?” While the two health conscious guys supported each other in eating healthy and rarely had dessert, both considered this a special occasion. Bob ordered cherry pie with ice cream.

When they returned from dinner, there was no conversation about what might happen. They went directly to the bedroom. Bob, with mixed emotions, wanted to give his virgin ass to his man. While he desired the connection he would feel as Mike entered him, he feared the pain his ass would endure from being pierced. This fear was highlighted by Mike’s reaction earlier.

Remembering the first time web site’s suggestion for extensive foreplay, Mike decided to prolong the pre-fuck activity. When they entered the bedroom, Mike laid on his back and opened the tube of K-Y and generously lubed his dick. Bob laid next to him and put some on his dick. They both gently stroked each other’s slippery dicks. Then Mike sat up and put more lube on his fingers. He gently rubbed around Bob’s ass. Bob told him it really felt good. Then Mike bit by bit inserted one finger. He felt Bob get tense. He leaned forward, keeping his finger in the ass, and kissed Bob. “Be calm, my man. I would never hurt you. If you say ‘stop’ I will stop. Relax.” They kissed as Mike kept his finger in Bob’s hole. He gently moved his finger in and out.

“Ummm. That feels soooooooooooo good,” Bob said. Mike continued finger fucking the virgin hole as he leaned in, kissing his man. This time, Bob felt pain in his ass. However, he did not want Mike to stop. He endured the pain and moaned, half from the pleasure he was receiving and half from the pain. Mike took his finger out and applied some more lube. When Mike gently reinserted his finger, Bob cried out softly from the pain. Mike asked if he should stop. “No way!” Bob said. Finally, there was less pain.

Mike asked if he was ready. Bob told him he thought so. Bob knelt in the cowboy position over Mike who was still on his back. Mike gave himself a couple of strokes to intensify his hardness and pushed it against Bob’s hole. He pushed in less than an inch (2.5 cm.). Then Bob asked him to stop. “Please pull out. It hurts.” Mike pulled out and gently massaged the outside of Bob’s hole while holding him.

“I’m sorry. I thought I could.”

They laid there for a while. Then Bob suggested, “This time, let me go down on you. Don’t push up. Let’s try it again.”

With Bob squatted over Mike’s hard dick, while facing him, he lowered himself, and inch by inch, slid down onto Mike’s dick. He told Mike not to move. It was painful. He hoped his asshole would get accustomed to Mike’s dick. Gradually, the pain lessened. Bob moved up and down slightly. “That hurts like hell yet feels fantastic. Don’t move. I am going to make your dick fuck my ass.”

Slowly Bob moved up and down. In less than 30 seconds Mike cried out, “I’m cumming!” Mike thrust up and Bob could feel him throbbing. As Mike’s dick pulsated while it filled the condom, he gave one more big thrust up. The pain Bob felt was nowhere near as great as the pleasure he experienced. He grabbed his own cock and with Mike still in him he shot all over Mike’s chest and face with a big glob landing on the smiling mouth. He was surprised at the intensity of the eruption, as he had only stroked himself a couple of times before he shot. Bob fell forward onto Mike. As Mike’s dick slid out of Bob’s hole, they kissed with Bob tasting his own cum on Mike’s lips.

“My ass hurts like hell you, raunchy bastard! But, give me time to recover and we will do it again. I am now an addicted bottom to your dick!”

They quietly laid in bed, each with thoughts concerning what had happened. Bob blissfully considered his feelings as he had submitted to his love. It had been an amazing feeling. He hoped Mike enjoyed ramming into him as much as he loved it. Mike next to him was having different thoughts. He had mixed feelings about the experience. Would he be able to give his love’s dick the pleasure his felt?

As the sun streamed into the window, Bob woke. He observed the sleeping mate who had kicked off his blanket and displayed a glorious morning woodie. When Bob returned from his morning piss, Mike was awake, laying on his back with his extended dick pointed up. Before getting back in bed Bob reached for a condom and rolled it on Mike. He then squatted over his friend and soon was enjoying another ride. Again, the pulsating of Mike’s dick cumming brought Bob to a simultaneous blastoff onto Mike’s chest.

Bob got up and returned with a damp towel. He cleaned his cum off of Mike and pulled the condom off the soft dick. As they snuggled, Mike told his love, “I want to try again. My ass says ‘NO’, but my heart says ‘YES’. Hopefully, if we take time out for breakfast, our bodies will be rejuvenated following our wake-up cums, and we will be ready for another round.”

Bob reached for Mike’s soft dick as he replied, “Sounds like a plan. Give my dick ten minutes and it should be very ready, very willing and very able to take care of my man.”

By the time the two naked men finished their coffee, cereal and fruit, both had rock hard dicks as they placed dirty dishes to the sink.

Bob decided the same long foreplay session Mike had used would hopefully both lubricate him for easier entry as well as heighten his desire to the point that any pain would be overshadowed by pleasure.

Bob told his love to lie on his back. Bob then straddled him in the same position they would be in for the fuck, except then, Mike would be on his back. Bob leaned forward and kissed his man. He then brought Mike’s left hand to his lips. After sucking and kissing each finger, he ran his tongue down the arm, briefly nipped the manscaped arm pit and let his tongue move across the chest to the other pit. Following a brief pit nip, his tongue licked up the arm to the right hand and then made love to each finger. After moving his tongue to Mike’s lips, they deep kissed. Then, he caressed and nibbled each nipple. After sliding his tongue down past the stomach, each ball was kissed. Ignoring Mike’s hard and now wet dick, Bob continued and gently caressed each foot and toe with his hands and then tongue. Realizing the level of Mike’s arousal could result in an early cumming, Bob ignored the dick. He then squeezed a generous amount of lube on his finger and gently spread Mike’s legs. He moved his hand down between the spread legs while bringing his head up to Mike’s. As his lips touched Mike’s, his finger massaged around the tender hole. Mike responded with a soft moan. As he continued the hole massage, Mike spread his legs further apart to encourage the soft touch. As their lips touched and tongues kissed, Bob gently inserted one finger. Mike responded with a moan. Bob gently finger fucked going no farther than an inch (2.5 cm). Mike responded by wrapping his arms around Bob and raising his ass. Bob finger fucked deeper. When his finger touched a certain spot, Mike yelped.

Bob asked, “Did I hurt you?”

“No, just the opposite! Just keep rubbing that place!”

Bob was afraid that if he continued, he would bring Mike over the edge before the fuck, so he gently withdrew his finger.

“Why did you stop?”

“Because it is time for the real thing.”

As Bob rolled on a condom they reversed positions. The two assumed the cowboy position with Bob on his back and Mike kneeling over him, ready to ride. Bob forced Mike to slow down. He was afraid that Mike’s passion was so high that he might go too deep too soon and again suffer fuck-stopping pain.

As Mike leaned back on the ready dick, Bob advised, “Go Slow. Just take a little and then stop. Then a little more.”

Mike slowly lowered himself. The pain was there, but so was the pleasure. Slowly, slowly, slowly, Mike pushed down and then raised up. As he leaned forward the implanted dick rode up. As he leaned back, the dick dug in deeper. The pain was intense, but so was the pleasure, a feeling that he could not describe. As he leaned back, the dick head touched that special spot. It was as if it had pressed a button that would start a motor. As soon as the dick hit that spot inside Mike, his dick erupted. Although Mike had not touched his dick, it shot harder and further than ever. As the dick throbbed, his hole contracted, gripping Bob’s dick. Between the sight of cum spewing over his chest and face, and the tightening of Mike around his dick, Bob blasted, filling the condom.

Mike fell forward. As his chest rubbed against his love’s cum covered chest, he kissed Bob’s cum-covered lips. As he embraced his friend, he realized his ass was stinging with pain. Then, he thought to himself, how true the statement, ‘No pain, No gain.’

The two lovers were now totally captivated with the feeling of both getting and giving.